Islamorada Vacation Rental 4.5 Star Review

Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wi-Fi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof t.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

114 Anglers Way
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many kid friendly features.
Outfitte.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.6 Star Review

Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced conk) is a three bedroom, two bath ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds and sip.......read more

5 Bedrooms - Sleeps 14
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port Antigua is one of the best neighborhoods in Islamorada. Not only does it offer a private beach, but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean just through chan.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe (south part of Islamorada). This home is the second one on the point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffeemaker, toaster, and blender. There are two flat panel TVs in the house, as wel.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

107 San Remo Drive - Comfortable Venetian Shores canal home that has two-bedroom one bath upstairs and a one bedroom one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened porch off the living room upstairs. The home has an awesome dockage that is 70'. Easy ocean or b.......read more

3 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct ocean views, and overlooks the resort style swimming pool. Dock space is available to rent as well for boats up to 31 ft.
This home is great for a family vacation. There is also a beach.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.4 Star Review

75691 Overseas Highway (aka Breezy Point Cottage) - With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this tr.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

We are so proud to say our tropical Bungalow now has 65 Straight 5 STAR REVIEWS on VRBO

What sets us apart from "just a vacation rental"? As your hosts, we have spent a lifetime in the hospitality industry. When we chose to purchase, remodel and refurnish the property we set out to achieve 6 main goals. LACBSC, or Location, Amenities, Comfo.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast access to both Ocean & Bay, fuel, bait, and provisions.

Key Features of Salty B:

- The House: Upstairs has Two Bedrooms, with a king-size bed in the Master, and a Full/Twin Bunks (2) in the other guest suite, There i.......read more

2 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your home away from home.
Fully remodeled home on the water, washer and dryer inside the house. TVs in living room and bedrooms. Smart TV and internet are included. Bedrooms include: 1 King Size Bed, 1 Queen Size Bed, 2 Full Size Beds.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is show up with your shorts and swimsuit. Boat slip is optional. You can be in your boat and heading out to enjoy spectacular fishing, diving, snorkeling, boating, or just cruising and watching the sunset in a flash.

Located .......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 4.6 Star Review

75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. View beautiful sunsets from the screened porch that includes tables and .......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Now available January and part of February - You will see amazing sunsets in our community sandy beach, fish or relax on pier, dip in the heated pool, take a few bikes for ride to Founders Park next door, slide over the water on our kayaks. You can also simply work from home from one of our TWO ready-to-go functional offices

Yes - Last minu.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Apartment

Waterfront one bedroom one bathroom located right on overseas highway on Islamorada. The shimmering blue hues of the Atlantic Ocean greet you upon arrival as the fun calls your name. Utilities are included which are water, internet garbage service and electricity. The apartment is fully furnished however it could possibly be rented partially furnis.......read more

1 Bedrooms - Sleeps 2
Apartment in Islamorada

Islamorada Condo

Fabulous 'Sea Breeze 41' is available for rent FURNISHED RENTAL A 30' Boat Slip is available in the CHC Marina. Available 03/20/2023 Experience high-end coastal luxury while staying in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally.......read more

3 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 4.5 Star Review

Executive Bay G-5 - Executive Bay is a bayside townhome that is sure to be your home away from home! This unit has been completely renovated and decorated beautifully with two bedrooms and three bathrooms. (1) King Bed, (1) Queen Bed with a bonus room off the Master that has 2 twin beds. Executive Bay Club is a bayside complex. It is a gated commun.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo 4.7 Star Review

Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 4 people. Stay in touch with family & friends with free wireless int.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Condo 4.9 Star Review

Beautifully renovated second floor condo at Futura Yacht Club, a private, gated complex with a fabulous marina and pool, just 67 miles south of Miami, at mile marker 88.5 in Islamorada, considered the Sportfishing Capital of the World.
Excellent access to the Ocean through Tavernier Creek or Snake Creek for boating, fishing or snorkeling. Relax.......read more

2 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Condo 4.9 Star Review

“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.

This 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental

Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have access to a large private sandy beach with zero entry to waist deep water to sit and sun bathe and bring the kids for a splash. 4 beach cruiser bicycles are included for riding around the neighborhood. The dock has a large fish cle.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Villa

Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two living spaces, downstairs and upstairs. You will enjoy amazing ocean views from the 3rd floor-viewing porch. Enjoy a nice lunch out on the dock, which includes a round concrete picnic table. Midnight Runner has all the amenities for .......read more

5 Bedrooms - Sleeps 10
Villa in Islamorada

Islamorada Villa 3.0 Star Review

Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean. Newly built-in outdoor shower! This home features an inviting living room with a sliding glass wall and a stunning 180-deg.......read more

4 Bedrooms - Sleeps 12
Villa in Islamorada

Islamorada Villa 4.9 Star Review

Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches, shopping, fishing, diving, snorkeling, bike riding, etc.

We provide bikes, kayaks and you can snorkel right from our dock. There are some resident iguanas in our mangroves and with luck you will see a manatee or great wh.......read more

1 Bedrooms - Sleeps 4
Villa in Islamorada

Islamorada Vacation Rental 4.9 Star Review

This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. You cannot go wrong with the protected boat basin for your boat or jet skis. If snorkeling, swimming or kayaking is your thing, look no further! Either enjoy amazing sunsets in the comfort of the backyard or walk to a fun local h.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

NOTE:
--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE.
--DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)
The bed configuration is different than the photos but the same beds are all there, as follows: Large bedroom with King bed an.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renovated in the last year. Serene and spacious outdoor area with brand new wooden deck, private pool and private homeowners beach. Two bedrooms/ two baths upstairs. Master Suite with ensuite bathroom. Second Master downstairs with ful.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with quick access to the Atlantic Ocean and Florida bay. The property offers lush tropical landscaping, 100 foot dockage. Outdoor covered living area with grill, dining table, and TV. The main floor has 1 master king with shower, and 2 ad.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in Bay Harbour, Islamorada Florida. This quiet gated community allows one to truly escape. Have the trip of a lifetime with Just a couple of friends & BRING YOUR BOAT too (up to 30')!

Amenities include; Large heated/cool p.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle to every place in town.
Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate u.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

This unique home gives you the quintessential keys experience. Nestled in a small, quaint gated, private community with ocean views, the house rests on a privately owned cove which empties into the Atlantic Ocean. The cove contains much wildlife including our neighborhood manatees. The community pool overlooks the Ocean affording spectacular view.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

*****New Owners/Listing so you may not see reviews yet for that reason******

***** Please email and I will answer any questions you have!*****


Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home has endless views of the ocean from every room. If you enj.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Welcome to the “Sailfish House” at Tarpon Point!

Soak up the sun and take in the spectacular views at this opulent 4 bedroom, 4 bath home located in the private community of Tarpon Point. Accommodating up to eight adults, this impressive home makes it easy to both entertain and unwind with its open floor plan and incredible panoramic vie.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for instant ocean and bay access. Totally renovated 3800 sq. ft home with all new furnishings. Open concept kitchen, dining room and living room...ready for your extended family with three bedrooms and three bathrooms upstairs, plus tw.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Mobile home 5.0 Star Review

Islamorada Windley Key affordable . 2 bedroom 2 bath rental. BRAND NEW PARK MODEL. Steps away from the gorgeous turquoise ocean. Bayside is also very close. Beautiful sunsets and sunrises.World class fishing, snorkeling, diving, Ecosystem, Founders Park close by -with all the amenities.
Theater By The Sea, swim with dolphins, mammals close by. .......read more

2 Bedrooms - Sleeps 5
Mobile home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small.......read more

4 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Apartment 4.8 Star Review

Welcome to our Green Turtle!
My family and I relocated to the beautiful Florida Keys, from Orlando. The property we purchased has a 1 bedroom, 1 bath downstairs apartment. We are conveniently located within miles of restaurants, shopping, parks, beach, grocery stores and retail stores. We are on a private road, surrounded by conservation for to.......read more

1 Bedrooms - Sleeps 2
Apartment in Islamorada

Islamorada Vacation Rental

Cozy, canal front, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. Excellent outdoor living and entertaining areas, summer kitchen, Wi-Fi, 65ft of deep-water dockage, a fish cleaning station, and a pool. Downstairs apartment with kitchenette and tw.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts, alon.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 3.3 Star Review

Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and has amazing views of the Atlantic. Some additional amenities:.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront three bedroom, two bath flat unit offers an open concept living and dining room with ocean views, an expansive kitchen with an island and bar seating, and large screened in porch overlooking the Atlantic. The m.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Villa 5.0 Star Review

3 story bayside home with its own beach. Great location. Private residential area, yet close to Everything. Due to unique location, one of only a hand full of homes on the island with views of both the Bay and the Ocean. Three (3) good sized bedrooms and 3 baths. Each bedroom has its own distinct views. The practical - high speed internet, s.......read more

3 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Bay Villa #9 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Bay Villa #9 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock along wi.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Cottage 4.9 Star Review

1940s Keys Cottage with *dockage available. Waterfront and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! We can arrange custom days of stay, less than 7 days, if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural waters edge property.......read more

1 Bedrooms - Sleeps 2
Cottage in Islamorada

Islamorada Vacation Rental 4.9 Star Review

PLEASE INQUIRE WITHIN FOR STAYS AND SPECIAL DEALS!!!

OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access.
This Open Water home HAS IT ALL.
-Brand New (Sept 2017) Huge, heated salt water swimming pool
-Brand New (Jan .......read more

4 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within a gated community with 24 hr. security. Includes fully equipped kitchen w/ granite countertops, microwave and s/s appliances; With washer & dryer, plasma TV, electric outdoor grill, cable, and phone. S.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Condo 4.9 Star Review

COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning and laundry.

Islamorada, Florida, is known as the Sports Fishing Capital of the Florida Keys. The Maison resort property in Islamorada is half way between Key West and mainland Florida. "Sunris.......read more

3 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This beautiful deep saltwater canal front 3 bedroom 3 bathroom pool home with an additional one bedroom one bath "in-laws" quarters is located inside of one of the finest neighborhoods in all of the Florida Keys - Venetian Shores. Inside, the home is fully equipped for entertaining, cooking, or just kicking back and relaxing. Outside the home offer.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.6 Star Review

132 Columbus Drive - Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in the house, you'll never want to leave. This two-bedroom two bath home has a great back porch, large yard and shaded carport/sitting area. Located in Lower Matecumbe, this house is close to downtown Islamorada, with shopping, grocer.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS —

A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys.   This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Introducing Maison Residences Unit 202, Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS —

A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys.   This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversize.......read more

4 Bedrooms - Sleeps 8
Condo in Islamorada

Islamorada Vacation Rental 4.9 Star Review

***POOL Built in July 2019; Tropical landscaping installed 2020/2021 with great privacy***

Located in Islamorada the premier Key of the Florida Keys, which is known as the Sports Fishing Capital of the world. Islamorada is actually made up of five Keys and this beautiful 3-story home is located in Lower Matecumbe Key, which in my opinion is .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.2 Star Review

113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! This home truly has an amazing water frontage. The home has plenty of room for your whole family to relax, having two bedrooms upstairs and two bedrooms downstairs!

Near the house is the small Anne's Beach. There are nature .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Reef is a quiet oceanfront community in the Florida Ke.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.1 Star Review

Windy Cove #1 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Port of Call C-2 - Charming two bedroom, two and a half baths condo with ocean views, a sunroom for a dining room, and newly renovated kitchen. Enjoy your coffee as you watch the sunrise over the Atlantic Ocean on your balcony or sit and relax in the pool. This great complex also offers a fantastic view of the Florida Keys from the rooftop deck, a .......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.6 Star Review

Welcome to Islamorada- the Fishing Capital of the World.

Oceanfront living doesn't get better than this. In the heart of Islamorada, this vacation home is located on the exclusive Millionaire's Row. Once you enter into the private oceanfront estate, you have arrived in paradise!

The house has two levels which are accessed via the ou.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

The Dock View House is one of three homes at Mermaid's Bay Boutique Estate. This private waterfront oasis sprawls 3.5 acres in the heart of Islamorada, just moments away from all of the top attractions and restaurants. The estate features over 300 feet of open-water views, a large boat basin and a resort-style pool and spa. 

This estate-sty.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering five bedrooms and three full baths on two living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equipped kitchen with .......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

TED’S PLACE

License # VR052 - Minimum Stay 1 Week, Saturday thru Saturday – Unbeatable Location - 1.5 acres – Bayfront – Gated & Secluded – Walking Distance to Lorelei and other great spots - 5/4 Home with Heated Infinity Pool and Hot Tub – Protected Dockage for Boats up to 30’ – Easy safe and secure parking for your boat tra.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Apartment

Great location in the heart of paradise! Small building in Islamorada, FL - centrally located. Next to great restaurants. Two bedrooms and one and a half bathroom. Full kitchen and king size bed in master suite. Heated pool, private beach, secured parking, billiards room, gym facilities, laundry room, party room by the pool. Enjoy beautiful sunsets.......read more

2 Bedrooms - Sleeps 4
Apartment in Islamorada

Islamorada Vacation Rental

This home has two master bedrooms with full baths and two kitchens an additional half bath. On the Ocean with large deck! Pool Hot Tub, Boat Slip!

Looking for the right folks that appreciate a very private unique property!.......read more

2 Bedrooms - Sleeps 3
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

DOCK RIGHT AT THE HOUSE! GUEST BATHROOM TOTALLY RENOVATED AND UPDATED! NICE PROTECTED DOCKAGE WITH DIRECT QUICK ACCESS TO CRYSTAL CLEAR ATLANTIC OCEAN! LOTS TO SEE AND DO CLOSE BY! EVERGLADES NATIONAL PARK JUST AROUND THE CORNER ON THE BAYSIDE!
WE ARE THE TYPE OF OWNERS WHO UNDERSTAND THE IMPORTANCE OF A VACATION! WE MAKE COMMUNICATION EASY .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the "Fishing Capital of the World". All amenities needed in order to enjoy a relaxing vacation. The property has a swimming pool, tennis court, pickleball court, shuffleboard, boat ramp and dock space for a boat up to 25' as stated in boat registration.
<.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Coral Harbor is the best kept secret in Islamorada. Quiet, gated community with ocean views, clubhouse, pool and a saltwater lagoon with beach. Minutes from all the best restaurants; both casual and fine dining. Great marinas, movie theater, Founders Park and 2 large grocery stores are all minutes away.

This spacious, 2/2 recently updated.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, tiki hut on private beach, heated pool and wireless .......read more

5 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled along Millionaire's Row in Islamorada on the Atlantic Ocean, Mile Marker 88.

Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, and a small sand beach. Peacocks are commonly seen on the property. The landscaping l.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.4 Star Review

Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on the Ocean side with lovely pool and dock.

Located near Morada way in the ‘Heart of Islamorada.’ Quietly located on the old road, walk or ride bikes to breakfast, lunch, dinner and festivals! A favorite for full moon pa.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Village of Islands Vacation Rental 4.9 Star Review

***Contact owner with description of group. *** Reach out to owner (from the contact owner section), to quickly get the most accurate open dates and rates.

WiFi Internet connectivity is provided.
Unassuming and relaxed elegance. Swim right off the dock or off Sea Oats Beach just out the front gate.
Great deep dockage and quick access.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada Village of Islands

Islamorada Villa 5.0 Star Review

Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great for eating your catch or simply enjoying a drink by the pool with your family and friends. Three bedrooms and three bathrooms on a quiet exclusive and private neighborhood. Minutes away from the best Islamorada restaurants and bars.......read more

3 Bedrooms - Sleeps 8
Villa in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Recently renovated! A beautiful 2 bedroom 2 full bath plus loft townhome located in Executive BayClub MM87, it is a private gated community (Bayside Waterfront) located in Islamorada, Florida Keys. Minutes from restaurants, attractions and grocery stores.

The unit is a two story with a third level loft. It has high end features and stainles.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Bay Villa #8 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Bay Villa #8 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock along wi.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with private beach , golf cart allowed on public road ,community access to private boat ramp. Will rent 3 month minimum to snowbirds From the month of November through April .Preferably to adults with no children and no pets. Access to 25'.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Key Lime Villa #3 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Key Lime Villa #3 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat doc.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Villa 4.8 Star Review

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air conditioned and there are ceiling fans throug.......read more

2 Bedrooms - Sleeps 4
Villa in Islamorada

Islamorada Mobile home 5.0 Star Review

One bedroom one bathroom mobile home located Oceanside on beautiful Windley key in Islamorada Florida keys the sport fishing capital of the world. This is a great spot for relaxing fishing and or exploring the keys situated 75 miles from Miami and 85 miles from Key West. Faces the ocean and gets cooling ocean breezes. Nicely furnished, very c.......read more

1 Bedrooms - Sleeps 2
Mobile home in Islamorada

Islamorada Condo 5.0 Star Review

Premier 1 bedroom unit with both that stunning bay view and a view of the pool off the balcony. Fully updated with the open concept kitchen open to the diving and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops through out the apartment. Comfortable queen size bed with a pull out couch in the Livingroom.......read more

1 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Villa 4.9 Star Review

Island Villa Rental Properties offers this two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83.

This stunning property is truly a tropical paradise with a private, sandy beach and observing pier.

Relax at the beach or cool down in the beachside pool.

The front home s.......read more

4 Bedrooms - Sleeps 10
Villa in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Futura Townhome #708 - Enjoy the spectacular view of the Florida Bay from either one of two balconies in this 2-story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TVs in the living room and master bedroom, phone (for local calls), a gas grill, and a charcoal grill.
There are tons of things to .......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Beautiful 5 bedroom, 3 bath pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a private apartment with two bedrooms, one has a queen and the other two queens. Has a full kitchen, living room, dining area and full bathroom. The second floor has three bedrooms, two with queens and the master has a king.
we .......read more

5 Bedrooms - Sleeps 13
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Escape to paradise and experience the ultimate vacation getaway at our stunning 4-bedroom, 3-bathroom canal home in the heart of Islamorada. Nestled along the crystal-clear waters of the Florida Keys, this exceptional rental offers a perfect blend of comfort, convenience, and natural beauty.

Key Features:
Spacious Accommodations: Our meti.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87

Our Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8.

Next door is Founders Park & Plantation Yacht Harbor.

A private gated community with 24hr security. The grounds have 2 tennis cou.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, dining, and fishing needs.
The Island-Design House is located in a quiet, private community with your own private gated sandy beach area with sunset views and crystal clear warm waters. For area info call or text Alexis .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

194 Airstream Lane - The most spectacular bay views from this stunning Islamorada home. This newly remodeled home offers three bedrooms and two baths upstairs with a beautiful kitchen and spacious living room overlooking the bay. Downstairs there is one bedroom and one bathroom, with another living room for guests. This perfect vacation home offers.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Maison Matecumbe #301 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centrally located right in the heart of Islamorada within walking and biking distance to many restaurants, cafes, shopping, marinas and Islamorada's Art District. The unit has been totally renovated and won’t fail to impress! Newly r.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo

Take a break & unwind at this charming Islamorada gem! Let this 1/1 bright & homey condo be your needed getaway to paradise. Take advantage of Islamorada’s breath taking waterways with access to the private boat ramp & dock with cleaning stations, water, electric, & trailer parking at first come/serve for a boat up to 25 ft in length. 300k liabil.......read more

1 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Bay Harbour D-114 - Beautiful modern luxury unit with three bedrooms and two full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room with Wi-Fi also included. The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish cleaning station, and Wi-Fi in th.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Villa 4.9 Star Review

The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Kottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ceiling.

The property is directly on Flori.......read more

2 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Vacation Rental 4.4 Star Review

* Beautiful 3/2 townhome with tile and wood floors, close to pool and beach
* 50' LCD TV with stereo system, DVD players, TVs in bedrooms, large sofa with 2 end recliners, large BBQ grill, washer and dryer
* Large Master Bedroom 'Sandy Shores' Room: King size bed & reclining chair
* Second Bedroom 'Nautilus' Room: Queen siz.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to the ocean by boat. 70' dock, fish cleaning station, commercial ice maker, bait freezer, outdoor rod racks and wash down stations make getting on the water quick and easy. Cool down at the end of the day in our new pool and at ni.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This is a brand new house. Just completed August 2014

This unique Gulf Front property is located among Gumbo Limbo, Mahogany, Royal Ponciana and palm trees sprinkled with other tropical foliage set directly on the Florida Bay/Gulf of Mexico. Hammocks and swings hang from the trees offering places to take frequent naps. The fabulous beach.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Conch Villa #4 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Conch Villa #4 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock alon.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Bay Villa #7 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Bay Villa #7 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock along wi.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

This Property is fully insured for rentals and licensed by the Village of Islamorada, license #VR-228.

Welcome to 134 Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our av.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Conch Villa #6 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the Art District of Islamorada. Conch Villa #6 offers three bedroom/three and a half baths and is fully furnished, has private decks with water/sunset views right on the bay! Guests can enjoy the property’s bayside boat dock alon.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

COVID-19 Update: Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning. and laundry.

Islamorada Florida is known as the Sports Fishing Capital of the Florida Keys. Our custom designed and built 5000 square foot home, “Sunset Reef,” is half way between Key West and ma.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

For the ultimate Keys experience, little can compare to settling into a custom-built home boasting its own private beach. Crafted with pleasure in mind, this luxurious five-bedroom, four-and-a-half bath house overlooks a full-size lap pool. Visitors can float on their inflatables, while contemplating the ocean, or, walk the soft-sand beach while da.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Villa

Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat included. Bicycles available. Close to many restaurants, bars and places of interest........read more

2 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Vacation Rental 5.0 Star Review

THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE TREES, BUT FOR PANORAMIC UNOBSTRUCTED OCEAN VIEWS - FROM INSIDE AND OUT - THERE IS ONLY ANGLERS REEF 140! See our many REVIEWS, which tell it all! Our home is known as "Aqua Vistas" and for good reason: THE OCEAN VIEWS DON'T GET ANY BETTER THAN FROM THIS HOME - inside from every room .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Apartment 4.9 Star Review

Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. Contact us for our available dates.

***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND AVAILABILITY FOR ALL SE.......read more

1 Bedrooms - Sleeps 2
Apartment in Islamorada

Islamorada Condo 4.9 Star Review

Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite cou.......read more

3 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This charming home sits on a large tropical lot (100' dock) with a great tiki and a large hot tub for late afternoon relaxation. Venetian Shores is a beautiful, quiet neighborhood perfect for strolling, jogging and bicycling. There is covered parking for one vehicle and a long driveway, and space to store a boat trailer off of the driveway. The ho.......read more

4 Bedrooms - Sleeps 9
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Latitude Adjustment, Islamorada, Florida
This home is our families' paradise in the Florida Keys and we want to share it with you.  When our family is not using it, it is ready for you to make your own memories. This home offers much more than your average resort stay -- and is a perfect home base for all of your water activities: snorkeling, .......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Relax and enjoy the Florida Keys lifestyle and outdoor living with full wrap around terraces. PLEASE NOTE: 28 night minimum rental. Seasonal rates available.

The Space

Recently renovated and beautifully furnished!

Pool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the who.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Beautiful home, facing ocean views indoors and out!
The house affords breath taking views of the atlantic ocean, Snorkel right off the shore line or fish right at the end of the dock for many you are a boater bring your boat and enjoy excellent fishing straight out of the dockage, the depth at low tide at the end of the dock is 2 feet. There a.......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Enjoy camaraderie with family and friends in this well-appointed, three-bedroom, ranch-style house in a lovely, private, Atlantic oceanfront, small gated-community setting; complete with large heated community pool and protected cove, and deep-water boat slip. Fishing boats, captains and crew abound in Islamorada's fishing capital environment. Re.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with two bedrooms, two full baths, full modern kitc.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.0 Star Review

75731 Overseas Highway - You are overcome with tranquility and relaxation as you pass through the gates of this oceanfront estate. You are greeted with ocean breezes and luscious landscaping making you feel like you've entered your own little oasis. This French Caribbean home has a large infinity pool, a private oceanfront beach, incredible porches.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Large Pool home in Venetian Shores in Islamorada, Florida. Mile Marker 86. 2 story home with 3 private bedroom suites with two suites on first level so no stairs. Formal dining room, family room, and large kitchen. 10,000# boat lift & large waterside chickee making outdoor entertaining a pleasure. Immediate ocean/bay access via Snake Creek. Paddl.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. Our home is a 2/2, and can comfortably sleep four, with two bedrooms upstairs. The Master has a queen bed, and a private bath. The second bedroom ha.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Adorable Key West style home for rent monthly in Anglers Reef. Small gated community located at MM 85 in Islamorada. Beautiful oceanfront pool, two beaches and a very convenient marina just stops from your front porch.
Call me for more information 305-240-0592.
Two bedrooms and two and a half baths with all the comforts of home. The mast.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

REDUCED BY 20% FOR LATE SUMMER/EARLY FALL.....Enjoy this stylishly remodeled townhome in the Heart of Islamorada at Executive Bay Club. This 7-guest retreat features top-of-the-line appliances, comfy furnishings, and a large patio with BBQ with a view of the Bay! Access all of the resort amenities including a beach, marina, swimming pool, tennis/pi.......read more

2 Bedrooms - Sleeps 7
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This canal front two bedroom two bathroom home offers a large open living area with kitchen and dining rooms opening to a large screened patio with ocean breezes - just a couple of homes away from the open ocean with unobstructed ocean views.
As you walk up the exterior steps you enter the main floor patio which is screened in and overlooks the .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Welcome to your dream vacation home in Islamorada, the jewel of the Florida Keys! This 3-bedroom condo boasts a prime location, with breathtaking views of the crystal-clear pool, Atlantic Ocean, and glistening white sand beach.
As soon as you step inside, you'll be enchanted by the bright and airy living space. The living area and balcony featur.......read more

3 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Check out our video tour! All NEW Anglers Reef Villa 103, a modern seaside retreat offering relaxation at its finest. Our Villa is perfect for families or couples seeking to make the best of their Florida Keys vacation. Enjoy a fresh cup of coffee each morning on the Patio or Even from above on the balcony and take in the fresh seaside air. Cook me.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Check out our video tour! All NEW Anglers Reef Villa 116, a modern beach retreat offering relaxation at its finest. Our Villa is perfect for families or couples seeking to make the best of their Florida Keys vacation. Enjoy a fresh cup of coffee each morning on the Patio or and take in the fresh seaside air. Cook meals with ease in the open and ful.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Island Villa Rental Properties offers Seas The Day in Islamorada, Florida Keys. Seas the Day is a fun, 4 bedroom house set on Lower Matecumbe Key in the beautiful Islamorada. On visiting the property, you ll first notice that it s just 3 small lots away from the Atlantic Ocean, and almost a straight shot to Alligator Reef Lighthouse (some of the m.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida Bay.
There are 3 bedrooms and two bathrooms upstairs, and a downstairs bedroom suite with private bathroom that opens onto the pool deck. The upstairs bedrooms are furnished with two king sized beds and one queen sized bed. Do.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people.

The Upper & Lower Duplex are each 1,500 sq ft uni.......read more

5 Bedrooms - Sleeps 18
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Completely renovated with Mom' touch, 2 story with spiral staircase bayside townhome at Executive Bay Club. Mile Marker 87.2./Aprox. 1300 sq. ft./ 2 bedrooms(1 King) 2 baths. Large living room and dining room. Breakfast
area. Fully furnished. Tile floors. Updated kitchen w/granite top
counter and top of the line brand named appliances. WI-F.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

- VR#258 - Saturday check in preferred, message for alternate days. 2 bedroom and 2.5 bath at 117 Anglers Way

Awesome family get-a-away in beautiful Islamorada. The ocean views from the back decks are amazing. The Oceanfront pool is serene! The gated community is a family friendly immaculately kept flora fauna park-like setting. Perfect for.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Venetian shores 4 bedroom 3 bath, pool, hotub, 300lbs ice machine with 20K boat lift, Master has a double walk-in shower, separate 1 bedroom with full bath on lower unit great for privacy, full kitchen with al stainless appliances.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo

This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated community. Includes a 30 foot boat slip in a protected marina with direct access to the ocean. Eat in kitchen with breakfast bar open to living area that looks out over the water. Expansive patio for open air dining or lounging. Main .......read more

2 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Apartment

Luxurious condo located at Mile Marker 75 on the Bayside in Islamorada.

Spacious Penthouse with every update possible is ready to become your vacation home on Islamorada. It has 4 fully staged bedrooms, 2 balconies, private rooftop lounge overviewing the ocean, movie room and gym room (can be used as an extra bedroom with a pull down king .......read more

5 Bedrooms - Sleeps 10
Apartment in Islamorada

Islamorada Vacation Rental 4.4 Star Review

Welcome to paradise! This waterfront home is in the heart of the Florida Keys. This 3 bedroom 3 bath home comfortably sleeps 10 adults. It features a 75 ft dock w/ a community boat ramp, full modern kitchen, spacious living and dinning area upstairs and downstairs. Charmingly furnished, the home also includes a washer/dryer, a/c, wifi, flat screen .......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Condo

This special place is close to everything, making it easy to plan your visit. Beautiful updated 2 bedroom 2 bath waterview condo in the much desired Coral Harbour community of Islamorada. Large outdoor patio and dining space. Updated furnishings and decor throughout. Open concept living and dining area with views to the lagoon. Community pool, mari.......read more

2 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled.... everything is tasteful, high quality, spotless and NEW!! HI SPEED WIFI and NetFlix is INCLUDED! Luxury heated pool / spa! Surrounded by a spectacular Dominican coral paver deck that does not get hot and has superior non skid p.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Breathtaking 3bedroom 3bathroom oceanfront vacation home is ready to welcome your family for your next getaway. Enjoy sunrises ad private beach views right from your bedroom. This house was built in 2019, and was only used by the owner. It features all new appliances and has everything you might need for an unforgettable vacation.

During yo.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.3 Star Review

Clean & updated oceanside canalfront home. Located at desirable
Lower Matecumbe in the Village of Islamorada,
M.M.74.Boat ramp on property,just pull up with your boat, launch, and
your off to fish or dive. Excellent deepwater dockage for up to a 29' boat,
fish cleaning station. Direct ocean & bay access. All the
comforts of home........read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs. Kitchen is fully equipped and recently renovated. Tile flooring throughout the home. Washer and Dr.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 degrees of breathtaking ocean vistas and four oversized bedrooms, each with their own bathroom.

On the main level, you will find the fully appointed chef’s kitchen which includes the finest high-end appliances to satisf.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Welcome to Executive Bay Club ~ Islamorada’s Hidden Gem!

This townhouse is located in the heart of Islamorada and offers everything you need for the perfect Florida Keys vacation. This fully upgraded unit is one of few that features 3 bedrooms, 3 full bathrooms, and even a loft with extra sleeping space. The modernized kitchen is fully sto.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Casa De Bliss - Canal front Venetian Shores...Unwind on your trip to the Keys at Casa De Bliss. This four bedrooms, four-and-a-half-bathroom house is located on a deep-water canal in one of Islamorada’s most sought-after neighborhoods, Venetian Shores. The spacious main living area and open kitchen are perfect for preparing meals together while e.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.3 Star Review

Enjoy breathtaking sunset from your own private beach.
Cottage nautical townhouse with your outside terrace.
Best restaurants in the keys are in Islamorada. Directly next door to Founders Park walking distance........read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Paradise Found! Enjoy fantastic sunsets in an updated 1400 sq. ft. townhouse in beautiful Executive Bay Club, on mile marker 87 in ISLAMORADA, Florida!

Amazing amenities- private beach with fishing dock, freshwater pool, clubhouse,
tennis/ pickleball courts in a private, gated community with 24-hour security. The waters are filled with ab.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Your slice of Islamorada awaits at the Key Lime Cottage! Located in the heart of the Florida Keys yet set in its own oasis, this charming 2 bedroom, 1 bath home with a full kitchen, access to a gorgeous (heated) community pool with only 6 other homes, outside patio with grill, beach chairs and key lime treats - there is something for everyone!
<.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

**Please contact owner directly via email if dates do not appear on calendar**

The Florida Keys can be considered the American Caribbean and features all the same amenities as other island destinations such as world class sport fishing, scuba diving and snorkeling, boating, sailing, kayaking and eco-tours.

Start enjoying the Florida.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Bayfront beautiful double townhouse with stunning bay views. Watch the sunsets from your balcony or from the beach right outside. This one a kind unit offers 4 bedrooms, 3 bathrooms and over 2800 square feet of living and entertaining space. Located inside of Executive Bay Club. Amenities include a sandy beach, large swimming pool, clubhouse, tenni.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo 4.7 Star Review

BEAUTIFUL REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUSTOM KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER, GLASS STOVE COUNTER TOP, MICROWAVE AND GARBAGE DISPOSAL. B.......read more

3 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Welcome to paradise! Come and relax in our beautiful newly renovated townhome in Islamorada. The executive Bay club is located in the sportfishing capital of the world. This is private gated community includes a heated Olympic size swimming pool, a clubhouse, two tennis court, a private beach where you will find a fishing and boat dock and and th.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo 4.6 Star Review

Executive Bay Club Condo M-1

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retrea.......read more

2 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Introducing the "Bonefish House," at Tarpon Point!

This opulent, luxury, home is equipped to accommodate eight adults with 4 bedrooms & 4 full bathrooms. The open living space offers easy entertaining and direct panoramic views of the community pool and Atlantic Ocean. The well-appointed and fully equipped chef’s kitchen offers the finest .......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

*3 Bedrooms, 2 Baths, Single Story Charming Keys House, Washer /dryer, Wifi/cable, backyard is completely fenced in

*strategically Located Between Miami and Key West( 2hrs from Ft Lauderdale International Airport & 1.5 Hrs from Miami

60 Foot of Dock With Electric & Water ; no fish cleaning station
Easy access to both Bay Side & .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Salty air and ocean breezes!
This 3 bedroom / 3 bath oceanfront home is located on the breathtaking key of Lower Matecumbe. Its new coastal inspired furnishings, add to the salty, beach charm.  It is equipped to comfortably sleep 10 adults, (2 queens, 2 twins, 1 pull out sofa, and 1 futon.) The charming kitchen is well stocked with everyt.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Townhome with all extras. Keys style with beautiful furnishings, newly remodeled with three bedrooms plus oversized loft with two full baths and many pluses. Across from marina and beach. Great community next to famous Founder's Park. Hurricane impact, Gated community with security. Always full of relaxing areas or areas for recreational fun l.......read more

4 Bedrooms - Sleeps 9
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Introducing “Bayview Paradise!”

This home rests in the midst Islamorada, also known as the Sport Fishing Capital of the World. If fishing is what you’ve come to the Keys for, this home gives you up to 80’ of dockage with 50amp shore power on an extra wide canal. Being one property away from the Bay, and within minutes from Channel .......read more

4 Bedrooms - Sleeps 9
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Welcome to the "Keys Life Cottage!"

This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned restaurants, breweries, marinas and boutiques in the F.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Islamorada

Islamorada Condo 4.7 Star Review

Escape to the breathtaking Gulf View Retreat in the highly coveted Bay Harbor community! Prepare to be enchanted by this hidden gem, nestled on the pristine shores of Lower Matecumbe Key in Islamorada, eagerly awaiting your arrival for your next unforgettable vacation. Discover the allure of Bay Harbor, a captivating four-building complex offering .......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Condo 4.0 Star Review

Cozy condo in Islamorada, mile maker 76.5. Walking or biking distance to Robbie's where you can feed the tarpons. Close to great restaurants and shops. 5 minute car ride to Anne's Beach. Canal view. Amenities: Pool with restroom and outside shower on-site, tennis & pickleball courts, Bar B Q Area with tiki, outdoor shuffleboard and horseshoe gaming.......read more

1 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental

The perfect Islamorada getaway awaits.

Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, a private sandy beach and protected dockage, canal-side.

This duplex features 3 bedrooms and 3 baths with an open layout for a spacious kitchen and dining room, and a living room with wall to wall sliding glass doo.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private beach, this townhome is the perfect Islamorada retreat.

This bayfront home features 3 bedrooms and 2.5 bathrooms, townhome style. The main floor offers a fully equipped kitchen, open living and dining room with water view.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

4 Bedrooms - Sleeps 16
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 3.0 Star Review

132 Atlantic Lane - Looking for your next home away from home You cannot go wrong with this recently renovated two-bedroom two bath canal home in Lower Matecumbe at the 76-mile marker. This home has everything you need for your next get-away in Islamorada. Only one property away from the Atlantic Ocean, you can literally watch the sun rise from the.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Alligator Reef - Conch Home - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced conk) is a three bedroom, two bath ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds a.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Come, Enjoy and Relax in our beautiful piece of PARADISE in the Florida Keys. The Executive Bay Club is located in Islamorada, the Diving/Snorkeling and Sport Fishing Capital of the world! This is a private, gated community with 24 hour security and easy accessible parking. The grounds have 2 tennis courts, heated swimming pool, club house, private.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Little Bay Upper Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Upper Duplex is a 1,500 sq ft unit with two bedrooms, two full baths, full modern kitc.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

125 Porto Vista Ct - No shoes, No shirt, No problem! In this Pt Antigua Pool Home, you will need to go nowhere to have an incredible Islamorada vacation!
Step inside this modern, updated, three-bedroom two bath and you'll never want to leave. The spacious open floor plan provides plenty of room for you and your guests to relax after a long day .......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And Queen Size Second Bedroom,sofa Bed In Living Room,extra folding bed, 4 Balconies, Gas BBQ, Satellite TV and WiFi. Carport For Two Cars. Pool, Tiki Hut. End Unit Provides Extra Sunlight And More Privacy. Boat slip .Boat rental ava.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 3.7 Star Review

141 Ocean Lane - "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the two-bedroom, two-bathroom house offers a 270-d.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

VILLAGE. RENTAL LICENSE # VR-007
Please always send email request with dates desired , as sometimes the dates on the calendar are not right.

From Dec 16 to April 16 are high season weeks/months.
From April 17 to Dec 15 are low season weeks/months.

House has access to all water recreational activities , close to open water and.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and generous space to enjoy the peaceful Keys atmosphere. Decorated in the fresh, natural hues of Islamorada and equipped with an incredible selection of amenities, each of our guest rooms and suites is infused with the easy elegance of.......read more

3 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.0 Star Review

Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% APRIL-JUNE!!

This amazing townhome features two bedroom and loft for your comfort is newly remodeled spacious townhome!! Owner has spared no expense with top of the line appliances, furnishings both indoor and outside. Unit features.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

20% OFF FROM APRIL-JUNE!!!

This 3 bed/2 bath features an open and spacious floor plan! Enjoy king beds, great sound system, oversized patio w/ BBQ and free parking in this gated Islamorada community with amazing amenities! Swim at the private beach or freshwater pool, Enjoy two tennis/pickleball courts, fishing off the jetty or strolling u.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This Keys Home is Located in Beautiful Port Antigua. 4 Br/ 3 Ba Sleeps 8 Comfortably. All Rooms Have Queen Sized Beds. Large Kitchen and Dining Room. Large Gathering Areas Throughout the House. There is Also a Barbecue and Gas Stove Downstairs. Features 60' Dock for Your Boat With Deep Water Access to the Florida Gulf and Atlantic Ocean in Minutes.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Cottage 5.0 Star Review

Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house sanitized when one guest leaves and another enters. We take pride in having our home immaculate and now we are taking extreme measures to have our guests feel safe during their say.

This downstairs portion of a dual family .......read more

1 Bedrooms - Sleeps 4
Cottage in Islamorada

Islamorada Villa

Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, relax in our hot tub or explore in our kayaks. Private boat ramp and boat slip!!.......read more

2 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Condo 4.9 Star Review

Summary:
*We can accommodate up to 8 people if two people are under the age of 6*

This brand new, three bedroom, three and a half bathroom penthouse unit is located within a luxury beachfront community in Islamorada. The Maison is at the heart of Islamorada with its own 350 feet of private beach and a 150’ pier out over the water. This .......read more

4 Bedrooms - Sleeps 8
Condo in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Vacation Rental License No VR-001
WEEKLY RENTAL
Located on the peaceful upper Keys, in Islamorada, this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is is just 75 miles from Miami and 86 miles from Key West. The average temperature is 8.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Island Villa Rental Properties offers fantastic panoramic views of the Atlantic Ocean from this 7 BR, oceanfront home in Islamorada, FL Keys. Located at MM 77 on Lower Matecumbe Key, this gated estate has everything needed for a Keys vacation… Pool, beach, views and sunrises!

The grounds have it all— At first glance, the magnificent pool.......read more

7 Bedrooms - Sleeps 14
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Bay Harbour A-304 – Beautiful three bedroom two and a half bath luxury penthouse condo located at mile marker 74.5 bayside. This condo is nicely decorated, fully appointed, and very spacious for you and your family. The unit has a beautiful, screened lanai off the living room and master bedroom with brand new furnishings to relax and watch the su.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Apartment

400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Oceanside. Great fishing in canal no need to go to a pier. Private beach. 25 ft of rear dockage for boat. Located in a private community heart and soul of Isalmorada. This is an exclusive neighborhood with near by restaurants and stor.......read more

1 Bedrooms - Sleeps 2
Apartment in Islamorada

Islamorada Condo 5.0 Star Review

Unit B106
Bay Harbour is a gated community located at MM 75 bayside in Islamorada, FL.
We are new owners of this existing vacation rental.
The location is quiet with the most beautiful blues and greens to make you feel like you have arrived in paradise, without actually leaving the country!
Call me for more information 305-240-05.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

We own 3 other vacation rentals in Islamorada:
VRBO/1054019 (5 bedroom)
VRBO/1977457 (7 bedroom)
VRBO/689629 (2 bedroom)

Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by n.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Cottage 4.8 Star Review

Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage home features two private bedrooms, a fully stocked kitchen, and a spacious living area to accommodate up to 4 guests comfortably.



There are many sights to see and activities to enjoy nearby. Within just a mile from our co.......read more

3 Bedrooms - Sleeps 4
Cottage in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Relax in this beautiful and comfortably updated bayside home in Port Antigua. Relax in this designer waterfront cul de sac home with 4 bedrooms, 3.5 bathrooms and 95' of dockage. Home is fully equipped with everything you need from WIFI, linens, towels, cooking, large capacity washer/dryer, BBQ, etc. Take pleasure in all the amenities this home.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

VR-203 We are one of Islamorada’s limited number of licensed weekly vacation homes.

This magnificent home with direct amazing ocean views is located in Islamorada at Mile Marker 85 in the gated community of Anglers Reef.

A relaxing retreat, with amenities that include lavishly landscaped pathways, a serene tropical community pool ov.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Wake up and go to sleep to the sounds of the ocean. Sunrise and sunset views. The beach is right outside your bedroom window. Newly renovated one bedroom, full bath, full kitchen, living room. Sleeps four........read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Villa 4.9 Star Review

This beautiful villa is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84 and has access to one of the few privately owned boat slips. The homes boat slip is available for rent for an additional $350/week, paid after booking and gives you access to the deep water channel right in front of the .......read more

2 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Vacation Rental

Bay Harbour A-101 - Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the waterfront balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitc.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house sanitized when one guest leaves and another enters. We take pride in having our home immaculate and now we are taking extreme measures to have our guests feel safe during their stay.

This upstairs portion of a dual family f.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Angler's Retreat is a 2 bedroom, 2.5 bathroom single family home with picturesque, ocean views, privacy and space. The property is located in Angler's Reef, a boutique complex of 52 homes donned with quintessential Keys charm. Amenities include lavishly landscaped pathways, a serene, tropical community pool overlooking the Atlantic Ocean (heated in.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.6 Star Review

This beautiful 4 bedroom/ 4 bathroom home has a 60' dock. Its canal leads straight out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores; in Islamorada, the fishing capital of the world. You are practically surrounded by water with ALL sorts of water a.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a master bedroom with king bed and bathroom with a balcony that has ocean views. The second floor has a bedroom with queen bed and bathroom right off of the living room and fully equipped and updated kitchen with a huge island. There .......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, bedding, electronics, appliances & more. New heated pool with 8 person hot tub. A true keys gem! Monthly calendar bookings only. .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.4 Star Review

Windy Cove #3 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Special Fall Rates for these weeks: 11-07-20 to 11-14-20, 11-14- to 11-21.., and 12-05 to 12-12-20.

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tr.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Welcome to the captivating Marlin House, an extraordinary 4-bedroom, 4-bath retreat nestled in the scenic paradise of Islamorada. Prepare to be enthralled by its exquisite design, unparalleled amenities, and sweeping ocean vistas that grace every level of this remarkable abode. Your journey begins as you pass through the gates of Tarpon Point, an e.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.8 Star Review

Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare), the villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.

The villa itself comes with a fully-equipped kitchen,.......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Last Resort Too - Welcome to Last Resort Too. This private hidden gem is situated on two prime oceanfront acres with a sprawling sandy beach. The beautifully maintained grounds are lush and shaded by coconut palms. The main home consists of five bedrooms and five and a half baths. The main level includes three king ensuites as well as a custom-buil.......read more

6 Bedrooms - Sleeps 14
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Gorgeous 2 bedroom 2 bath condo all on one floor with HEATED POOL, DOCK FOR FISHING, AND OUTDOOR BALCONY. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you will find stainless steel appliances, a master bedroom with queen size bed with large outdoor balcony! B.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Condo 5.0 Star Review

? PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, WATER SPORTS and ACTIVITIES!

?WE ARE ONE OF ONLY A FEW LEGAL 7 NIGHT RENTALS IN ISLAMORADA AND THE FLORIDA KEYS -THERE IS A 28 NIGHT MINIMUM RENTAL LAW & ILLEGAL RENTALS ARE SHUT DOWN DAILY- BUYER BEWARE!

?CONCIE.......read more

2 Bedrooms - Sleeps 6
Condo in Islamorada

Islamorada Vacation Rental

Escape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis located in the heart of Islamorada. This five bedroom, 7 1/2 bathroom home features a spacious covered downstairs living area poolside, decorated in tropical themes of bamboo and coral. This area encompasses two living areas, a large.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

ONE-OF-A-KIND VACATION EXPERIENCE. You will never want to leave. Large open space, dining and living room. Private pool. Porch with view. Complimentary private beach for White Marlin Beach residents and guests........read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo 4.8 Star Review

Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat access on Gulf side fishing and snorkeling, you can be in the ocean quickly. WiFi internet, 5 large screen TVs all with internet access. Spectacular view, great diving locations and fishing........read more

3 Bedrooms - Sleeps 8
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE—-THREE CARPORTS——PROFESSIONALLY DECORATED/FURNISHED

*** This is a great house---beautifully furnished/well kept. Oceanview with 3 Carports!***

*** NO ROAD NOISE. This house does not back up to the Overseas Hwy and is very quiet and secluded within Anglers Reef! ***

**.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, which is a quarter mile from the house. A quick boat ride and/or key access if you’d like to travel by car. Dock space has over 60 feet with your own personal ramp (ramp only accommodates smaller boats, 3,000 pounds or less). Amazi.......read more

2 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Villa 5.0 Star Review

2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living amenities in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, back yard patio with barbecue, front porch seating, balcony, and fully equipped kitchen with granite counter tops. It also has v.......read more

2 Bedrooms - Sleeps 6
Villa in Islamorada

Islamorada Condo 4.0 Star Review

Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime condo, prime view and prime location. Just 30 feet from the Bay. All in one. 2 Bedrooms plus loft and 3 full baths. Totally remodeled and upgraded. New appliances, furniture, floors, you name it. No expenses spared. Spectacular wes.......read more

2 Bedrooms - Sleeps 7
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

See why we have ALL 5-star reviews! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.

As soon as you step foot in this stunning two-floor home, you're greeted by a gorgeous yet highly comfortable modern open-floor plan living area. It is styled elegantly to match the beauti.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of our guest rooms and suites is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual .......read more

1 Bedrooms - Sleeps 4
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

PROPERTY NAME: Harbor House
101 San Juan Dr., Islamorada, FL

LOCATION: Bayside Canal home located in the Upscale Venetian Shores Community

MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed

MILE MARKER: 86

DETAILS: Ready for occupancy this winter! This is a very special single fam.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

PROPERTY NAME: Pelican Landing
60 West Plaza Del Lago, Islamorada, FL

LOCATION: Bayside Private Home in the neighborhood of Port Antigua

MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed

MILE MARKER: 74.5

DETAILS: Pelican Landing is located in the prestigious neighborhood of Port.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

PROPERTY NAME: West Plaza
63 West Plaza Del Lago, Islamorada, FL

LOCATION: Bayside House

MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed

MILE MARKER: 74.5

DETAILS: "West Plaza Del Lago" will steal your breath away the moment you pull into the drive way. Beautifully remodeled roo.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

PROPERTY NAME: Blue Water Retreat
137 Ocean Lane, Islamorada, Florida

LOCATION: Oceanside Canal home located in Lower Matecumbe, Islamorada

MINIMUM: 28 Days, All stays must be the whole month(s), No Partial Months Allowed

MILE MARKER: 76.3

DETAILS: This home has it all - ocean side Lower Matecumbe location, remodel.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo

PROPERTY NAME: Beacon Reef #307
83201 Old Highway, Islamorada, Florida

LOCATION: Ocean side Condo

MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed
MILE MARKER: 83.2

DETAILS: This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath.
Entire house has been remodeled, fully furnished, with a 90 ft Dock. Bring your clothes, boat, fishing and dive .......read more

3 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Welcome to your personal paradise - a deluxe Keys retreat that promises to take your coastal living experience to the next level. This gated, canal-front property boasts a range of private features that will cater to your every comfort and recreational desire. Take in the tranquil views from your waterfront pool deck, complete with multiple seating.......read more

5 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

The Oasis - This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this lot than any in all the keys! The palm trees are some of the tallest as well and their graceful presence puts you in the Jimmy Buffett mode as the cooling Atlantic Ocean winds blow your hair and alleviate the heat.
When you relax in the .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Condo 5.0 Star Review

Escape to the Keys at this renovated condo in the heart of Islamorada. Walking distance from some of the best local restaurants as well as Bud N’ Mary’s Marina- you’ll be living like a true islander in no time! Your days will be filled lounging by the pool or relaxing down by the ocean. End the day hosting your own happy hour at the tiki bar.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in your private dock with 35 feet of dockage.Minutes to the bay and very easy access to the ocean.There is access to a private homeowners beach with Cabañas and outdoor charcoal bbq.The home has 3 bedrooms and two bathrooms upstair.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the world. Home is on the bayside in the upscale community of Venetian Shores. This spacious split floor plan home features 3 bedrooms and 2 bathrooms, open floor plan living area, screened in patio and large outdoor deck for your e.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo

This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities featuring 12 acres of lushly landscaped grounds, oceanfront pool & spa, club house, gym, tiki huts with grilling area, lighted tennis court and a marina with a boat ramp. This luxurious corner unit offers expansive panoramic ocean v.......read more

3 Bedrooms - Sleeps 8
Condo in Islamorada

Islamorada Hotel resort

We are committed to providing outstanding service and a great vacation experience to all of our guests. While Caloosa Cove Resort does not have accessible units, there are many accessibility features at our Resort. They include:

ADA Parking Spaces (van accessible) – must display a government parking permit
Accessible Routes – to reso.......read more

2 Bedrooms - Sleeps 5
Hotel resort in Islamorada

Islamorada Vacation Rental

New Listing! Exquisite Angler's Reef Villa Under New Management

Escape to Islamorada’s Finest Oceanfront Gated Community

Soak up the sun and enjoy the ocean breeze from this charming 2 bedroom, 2 bath Key West style villa located in the exclusive community of Angler’s Reef. Accommodating up to six people, this exquisite home mak.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.9 Star Review

Sun-kissed Bliss

Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'

This canal-side home is a tropical paradise, perfect for your next memorable getaway! Your renovated retreat features coastal-chic interiors and large picture windows that face the o.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Islamorada! Enjoy this beautifully furnished three-bedroom, two-bathroom unit with endless views overlooking ocean. This 12-acre property is truly an island paradise, complete with tropical landscaping, heated pool, beach, marina, te.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

fresh clean-no chemicals
Keys home and room decor private beautiful fenced in yard for pet, animal friendly,
newly renovated home located
on quiet private street,
on cul de sac, private inside parking space, private dock on canal on the ocean with ocean view and 2 beaches (1 private and 1 public) a block's distance away
The space
.......read more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Little Bay Cottage - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people.

The Upper & Lower Duplex are each 1,500 sq ft unit.......read more

1 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 3.7 Star Review

76004 Overseas Highway - Enjoy spectacular sunsets while drinking an iced cold beverage on the observation deck of this stunning home nestled back behind swaying palm trees. This home sits directly on the bay and has two bedrooms two baths upstairs and has a detached two-bedroom one bath apartment. The home is located at mile marker 76.
Near th.......read more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Hotel resort 4.8 Star Review

Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Caribbean home is on the ocean’s edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.


About The Caribb.......read more

3 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 6
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Welcome to The Bird of Paradise. This Oceanfront home has everything you need for a relaxing getaway. Custom High ceilings create an open, airy feel to this one bedroom, one bathroom home. The Bird of Paradise has a fully appointed kitchen with everything you need to cook up your fresh catch, or, use the Weber gas grill on your front patio. Just st.......read more

1 Bedrooms - Sleeps 4
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 6
Hotel resort in Islamorada

Islamorada Hotel resort

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

1 Bedrooms - Sleeps 4
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

1 Bedrooms - Sleeps 4
Hotel resort in Islamorada

Islamorada Hotel resort

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, o.......read more

2 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Caribbean home is on the ocean’s edge with 180 degrees of unobstructed ocean views and sunrises. With complete privacy, this site is home to famous movie shoots, celebrity weddings and family reunions.


About The Caribb.......read more

3 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Vacation Rental 5.0 Star Review

We own 3 other vacation rentals in Islamorada:
VRBO/1054019 (5 bedroom)
VRBO/689629 (2 bedroom)
VRBO/1576833 (5 bedroom)


Beautiful and new vacation rental with deep dockage on quiet basin in the heart of the Village of Islamorada! Super location – a 1 minute walk to the Lorelei Restaurant.
Manatees visit the dock area ea.......read more

7 Bedrooms - Sleeps 14
Vacation Rental Home in Islamorada

Islamorada Hotel resort

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpicked and custom crafted from the finest materials and builders.

Inspired by the Caribbean lifestyle and design from Ocean Gardens Showroom. The Jamaican Palm is an expansive 3 bedroom, two-bathroom single home with a large .......read more

3 Bedrooms - Sleeps 9
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 6
Hotel resort in Islamorada

Islamorada Hotel resort 5.0 Star Review

Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.

Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.

Guests enjoy the beautiful Caribbean décor and high, ope.......read more

2 Bedrooms - Sleeps 8
Hotel resort in Islamorada

Islamorada Vacation Rental

Three story traditional Keys home located directly on a channel with one of the best Atlantic Ocean/Bay access points in all Florida Keys through the world famous Snake Creek. This location is close to 5 of the best dive reefs in the Florida Keys! The home is located within 1-3 miles from Publix grocery store, Tiki Bar, Bass Pro, Starbucks, Founder.......read more

5 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Just under 1.5 hours from Miami International Airport, you will find the beautiful gated community of Executive Bay Club. This townhouse has 3 bedrooms, 2 full baths, and a private patio with bbq. The unit has been beautifully renovated, decorated, and has all the comforts for a relaxing vacation. Amenities include a private beach, dock, pool, club.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME**
Perfect Vacation Home in Islamorada, the center of the Keys Island. The house is ideal for a large family get away, or a small intimate escape. It is perfectly situated between canals providing guests with an unforgettable keys breeze. You are conveniently located near supermarkets, restaurant.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Windy Cove #2 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features three bedrooms and two bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak up the sun on the beach under.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Villa 5.0 Star Review

The "Nest" villa is one of only seven units nestled on a one acre native tropical hammock directly on Florida Bay with stunning water and sunset views. Although a hidden jewel, it is close to everything that beautiful Islamorada has to offer and is located only a 90 minute drive from Miami International Airport (MIA) and 2 hours from Fort Lauderda.......read more

1 Bedrooms - Sleeps 4
Villa in Islamorada

Islamorada Vacation Rental 4.7 Star Review

Beautiful waterfront home with 3 bedrooms two baths upstairs, 1/2 bath downstairs. New appliances, fixtures, furnishings etc. etc. Ocean views from the bedrooms , dining room and East balcony and lagoon views from one bedroom and back porch. The house is on a cul-de-sac in a quiet neighborhood, there is no thru traffic so it is very pea.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

This beautiful home is located in one of the finest neighborhoods of the Florida Keys- Port Antigua in Islamorada,FL with Private Beach, BBQ area, Boat Ramp, close to shopping centers and much more. Watch the sunrise from the 2 spacious terrace . This comfortable 4,200 sq ft sleeps 12 people comfortably with 5 bedrooms and 4 baths. No Pool or Dock.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

137 Lorelane Place - Welcome to the Lookout at Lorelane, your home away from home in the fabulous Florida Keys. From coffee on the patio to sunset cocktails on the rooftop, this home is your oasis in Key Largo. This beautifully renovated three-bedroom two bath located at the 100-mile marker on a deep water oceanside canal will not disappoint! Amen.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Villa

Unwind with a Bay view, approx. 1 hour from Miami airport. Access to mini beach, great sunsets and boat ramp, swimming, kayaks and paddle board. Fully stocked kitchen with organic oils and slices. Close to great restaurants, shops and just 1 mile to the best beach in the upper keys. White linens compliment teak furniture from Bali, Morrocan lig.......read more

2 Bedrooms - Sleeps 5
Villa in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Your island pool home awaits in Islamorada's Port Antigua! 3 bedroom, additional 2nd floor loft that serves as 4th bedroom with daybed, 3 bath, high ceilings, tile & hardwood floors, state of the art kitchen w/ concrete counters & top of the line stainless appliances. Open, spacious and perfect for entertaining is how this home was designed. Walk.......read more

3 Bedrooms - Sleeps 12
Vacation Rental Home in Islamorada

Islamorada Apartment

20% OFF AUGUST - MID-DECEMBER....under $150 per night for this amazingly remodeled and luxurios 2 bed/2 bath townhome with an open floor plan located in the incredible waterfront community of Executive Bay Club in the heart of Islamorada! Unit was recently purchased and fully remodeled with new kitchen, bathrooms, flooring and all new furnishings........read more

2 Bedrooms - Sleeps 7
Apartment in Islamorada

Islamorada Vacation Rental

Wonderful Keys home built and cared for by the same family since 1988. Located near MM 86, 2 hours from Miami, 2 hours from Key West, and a 10 min boat ride from the BEST sandy bottom sandbar in the Keys, the world-famous ISLAMORADA SANDBAR (Whale Harbor Channel). Truly a FISHERMAN'S DREAM, offering quick and easy access to WORLD CLASS FISHING on.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Private fortress-like vacation home in coveted Safety Harbor Lower Matecumbe Key of the Village of Islamorada. 100 ft on canal with concrete dock and room for up to 40 foot boat in water. Fish cleaning stations, water, shore power. Fenced access to property, heated private pool with spa. Nicely landscaped and very private. Huge open upper deck w.......read more

6 Bedrooms - Sleeps 15
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries.

Escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. This majestic property is over 2.75 acres of landscaped beauty. .......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downtown Islamorada. Just beyond the discreet gates, an easy walk or bike ride away, is all that this Florida Keys village has to offer boutiques, galleries, dining, spa relaxation, beaches and the ultimate saltwater fishing experiences.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

ISLAMORADA Vacation Rental 5.0 Star Review

SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half bathroom Spanish, Modern home in desirable Port Antigua.

This owner operated property is always clean, comfortable and relaxing.

Endless water views delight in every direction – incredible sunsets from the master .......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in ISLAMORADA

Islamorada Vacation Rental

Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2019. Wonderful floor to ceiling glass captures amazing ocean views. Warm reclaimed teak flooring. Fabulous ocean front views, 4 outdoor ocean view patios plus 1 small outdoor Master bath deck. Chef appointed kitchen with Wolf stov.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo

PROPERTY NAME: The Palms #417
79901 Overseas Highway, Islamorada, FL

LOCATION: Bayside Condominium

MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed

MILE MARKER: 79.9

DETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlan.......read more

1 Bedrooms - Sleeps 3
Condo in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Happy Tarpon - the best of the Florida Keys and the best of Islamorada! Enjoy privacy in our beautifully renovated home in the heart of Islamorada. It is furnished for easy tropical living inside and out. Swim in the heated pool after a day on the water. Boating, fishing, lobstering, sailboarding, skindiving or canoeing, we have it all. Your b.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Mile Marker 81.6 -- Key Lime Villa




Key Lime Villa, aptly named for the famous Key's citrus fruit, is a new construction Villa located in the heart of Islamorada. The Villa is tastefully furnished with modern styles and amenities. Guests can enjoy the use of the shared pool, dockage, boat ramp, and tiki hut located bayside. Locate.......read more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state parks, dive boats, and fishing charters! This townhouse is the perfect destination for those who love the bounty and beauty of the ocean.

You would be able to enjoy of the tennis court, pool, shuffle board, pickle ball, ti.......read more

2 Bedrooms - Sleeps 5
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

If you are looking for the perfect home base for your family gathering or friend getaway look no further than this quaint 3 bedroom home with private beach access. The exclusive White Marlin beach is just meters away, and sits alongside the colorful blue waters of the Florida Bay. With 2 King sized beds and 1 Queen, accommodations for 8, Our Wh.......read more

3 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental

Welcome to Casa Luca ~ A true Islamorada beach house paradise, providing its own private sandy beach with 100’ of water frontage and absolutely stunning panoramic views of the Atlantic Ocean. This beautiful home is located on the island of Lower Matecumbe Key, nestled on one of Islamorada’s famous sea turtle nesting beaches, also known as Sea O.......read more

5 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

2 bedroom, 2 bath with 1 king bed, 1 queen bed and 1 queen sleeper sofa. Sleeps 6. Boat dockage and Housekeeping NOT available.

Guests enjoy the beautiful Caribbean décor and open ceilings. Solid wood doors and windows, ceramic flooring. Open living and dining area all add to your tropical experience. You are just across the street from Th.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from ou.......read more

2 Bedrooms - Sleeps 8
Vacation Rental Home in Islamorada

Islamorada Vacation Rental 5.0 Star Review

2 bedroom, 2 bath with 2 queen beds and 1 queen sleeper sofa. Sleeps 6. Does not include Boat Dockage or Daily Housekeeping

Guests enjoy the beautiful Caribbean décor and open ceilings. Solid wood doors and windows, ceramic flooring. Open living and dining area all add to your tropical experience. You are just across the street from The C.......read more

2 Bedrooms - Sleeps 6
Vacation Rental Home in Islamorada

Islamorada Condo

Come to the Keys and enjoy this spectacular piece of property, an amazing vacation spot in the heart of Islamorada! Fully stocked 2 bedroom, 2 bathroom condo has everything you need.

Large heated pool, infrared sauna, bathhouses, and you can fish the flats from your 440ft lighted fishing pier.
Clubhouse, ping pong, TV, gym, BBQ grill, ka.......read more

2 Bedrooms - Sleeps 4
Condo in Islamorada

Islamorada Vacation Rental

This gated canal front home in Key Largo is great for large families. Featuring three bedrooms and two bathrooms upstairs and an additional bedroom, two bathrooms and extra room with a pullout sofa downstairs. The outdoor living was designed for entertaining with a shaded conversation area, covered grill and refreshing pool. The large concrete dock.......read more

4 Bedrooms - Sleeps 10
Vacation Rental Home in Islamorada

Islamorada Hotel resort

Topsider resort is a unique water front property where all the units are elevated and detached featuring 2 bedrooms & 2 baths with decks. Upon purchase you will be issued a Guest Certificate in your name issued through II for our week. The certificate entitles you to exclusive use for that week and all responsibility........read more

2 Bedrooms - Sleeps 6
Hotel resort in Islamorada