Islamorada Vacation Rentals, Beach Houses and Condos for Rent

Private Vacation Home in Islamorada

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 top patio and enjoy a beautiful sunrise of the glow of a famous Florida Keys Sunset.
NOTE: Onsite trailer parking is not allowed at Bay Harbour com.......

4.5 Star Review

Private Vacation Home in Islamorada

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.
Outfitted with his and her beach cruiser bikes, a pair of paddleboard/kayak crossovers, fishing equipment, pool toys, beach toys, snorkeling gear and much mor.......

4.8 Star Review

Private Vacation Home in Islamorada

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 your margaritas. The Conch can be rented on its own or with its companion home, The Lobster. The Lobster is a cozy two bedroom, two bath home directl.......

4.6 Star Review

Private Vacation Home in Islamorada

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 channel 5 or channel 2. Lots of amenities and restaurants in the area to list but will provide information at the property. On the second floor there i.......

3 Bedrooms - Sleeps 8
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

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 well as Wi-Fi internet. House is decorated with modern decor, and you'll love the water views from every window! Protected dockage enough for 2 boats! Th.......

4.7 Star Review

Private Vacation Home in Islamorada

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 bay access via Snake Creek. Walking distance to Founder's Park which you get free access to the park and a small beach area.
If booking more than a.......

5.0 Star Review

Private Vacation Home in Islamorada

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 and kayaks available. Lush, tropical landscape adorns this property. Call us today to reserve your stay........

5.0 Star Review

Private Vacation Home in Islamorada

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 traditional one-story Keys bungalow is refurbished. Its new owners have even given the house a name. Breezy Point Cottage, - they call it. Look out from.......

4.4 Star Review

Private Vacation Home in Islamorada

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, Comfort, Beauty, Cleanliness and Service. We hope that by reading our reviews you will feel we have met and continue to meet these goals to provide an exce.......

5.0 Star Review

Private Vacation Home in Islamorada

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 is one Bathroom upstairs and one downstairs. Downstairs has a queen-sized Murphy bed Enjoy the convenience of a first-floor bathroom, and refrigerator,.......

2 Bedrooms - Sleeps 10
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

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 and 1 Twin Size Trundle Bed. 1 Full Bathroom with Shower and an Outdoor Shower as well. 40 FT Dock available upon request. Food Mart in walking dista.......

3 Bedrooms - Sleeps 8
Vacation Rental in Islamorada

Condo in Islamorada

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 on Lower Matecumbe this condo is in the city limits of Islamorada....'Sport fishing Capital of the World'! This gated community is beautifully landsc.......

5.0 Star Review

Private Vacation Home in Islamorada

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 chairs. The roof deck allows for you to see both sides of the island! The bedrooms are located on opposite sides of the house with the common areas in.......

4.6 Star Review

Private Vacation Home in Islamorada

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 minute opportunity for a  in paradise! So, change your latitude, attitude and immerse your body and mind in the calming, soothing waters that surround o.......

4.9 Star Review

Apartment in Islamorada

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 furnished or empty to the right candidate. We also have an additional $1000 space if needed that can also be rented every 6 months to a year. HD Video avail.......

1 Bedrooms - Sleeps 2
Vacation Rental in Islamorada

Condo in Islamorada

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 decorated in Tropical Modern style. It features an open floor plan in the main living, dining and kitchen areas creating a warm and inviting setting........

3 Bedrooms - Sleeps 6
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

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 community with 24-hour security. The grounds feature 2 tennis courts, full size pool with bay views, fishing pier and clubhouse. Take a walk to the beach an.......

4.5 Star Review

Condo in Islamorada

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 internet. The master bedroom has a king size bed with two twin beds in the 2nd bedroom. If your children are small, we have a hi chair and various toy.......

4.7 Star Review

Condo in Islamorada

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 by the beach or heated pool during the day, and watch breathtaking Sunsets from our private sandy area by the Bay.
Free boat and trailer parking a.......

4.9 Star Review

Condo in Islamorada

“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 the many boat rental companies in the area. If your vacation is more about relaxation, then kick back at one of the near-by beautiful sandy beaches. .......

4.9 Star Review

Private Vacation Home in Islamorada

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 cleaning table and steps down into the clean water. Enjoy the breeze and the views from the downstairs covered entertaining area. No neighbors across the.......

5 Bedrooms - Sleeps 10
Vacation Rental in Islamorada

Villa in Islamorada

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 you and your guests to enjoy, at your private home away from it all!

Key Features of Midnight Runner:

- The Main Kitchen (Upstairs) incl.......

5 Bedrooms - Sleeps 10
Vacation Rental in Islamorada

Villa in Islamorada

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-degree ocean view. You'll love to call Turtle Nest "your home away from home".

Key Features of Turtle Nest:

-The kitchen includes all you.......

3.0 Star Review

Villa in Islamorada

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 white heron. Pelicans, cormorants and gulls are common. We have a private beach where you can chill out and relax and shady outdoor spaces to enjoy.
.......

4.9 Star Review

Private Vacation Home in Islamorada

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 hangout (88 Restaurant) for a homemade Island cocktail. Don t forget to enjoy the "Treehouse" with a card game or just to see a different view :). Bra.......

4.9 Star Review

Private Vacation Home in Islamorada

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 and a Queen bed up in the loft. Space for queen air mattress if needed. Second bedroom has a queen and two twin bunks.

Gorgeous, spacious condo .......

4.9 Star Review

Private Vacation Home in Islamorada

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 full bathroom and den/TV room with queen size pull out couch. Screened in terrace overlooking pool and canal. Flat screen TV's throughout the home. Five .......

4.9 Star Review

Private Vacation Home in Islamorada

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 additional bedrooms all with twin beds and bunks with bathroom. Anchors Away Boat Rentals can have a boat delivered right to the dock for your stay! 28 .......

5.0 Star Review

Condo in Islamorada

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 pool, jetted hot tub, fitness center, clubhouse, tennis courts, grills, covered parking + guest parking, and a private boat slip (Insurance required & .......

5.0 Star Review

Private Vacation Home in Islamorada

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 up to 6 adults plus children. The bright living area fully opens up to a private patio, where you'll love to gather by the heated plunge pool with a vi.......

5.0 Star Review

Private Vacation Home in Islamorada

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 views. Alligator Reef can be seen from the pool area (great snorkeling and diving spot) a just a short boat trip away. You are within walking or biking .......

4 Bedrooms - Sleeps 8
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

*****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 enjoy watching the sun rise, this home also features 800 sq ft of decking to enjoy the ocean views while sipping your morning coffee. For your convenienc.......

4.9 Star Review

Private Vacation Home in Islamorada

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 views of the Atlantic Ocean.

On the ground floor you will be greeted by the foyer that will lead you up to the main level featuring a comfortable .......

4 Bedrooms - Sleeps 8
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

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 two more bedrooms and a full bath downstairs. There is a full kitchen upstairs and kitchenette downstairs, plus laundry on both levels. There is also a .......

5 Bedrooms - Sleeps 10
Vacation Rental in Islamorada

Mobile Home in Islamorada

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. Mas. Bed. - Queen bed.
2nd. Bed. -1 full & 1 twin bunk beds.
Maximum 2 adults, children over 7 yrs. only.
JAN-MARCH 90 NIGHT MIN. STAY REQ.<.......

5.0 Star Review

Private Vacation Home in Islamorada

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 kitchen area. The pool is situated canal side and perfect after a long day of boating. Enjoy grilling your catch in your outdoor canal side kitchen. .......

5.0 Star Review

Apartment in Islamorada

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 total privacy. Deeded beached access for residents of our street only, allows you to launch our kayaks or paddle board from a private convenient locatio.......

4.8 Star Review

Private Vacation Home in Islamorada

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 two bedrooms perfect for multi- family vacations! Grab your sandals and bathing suits and come enjoy this beautiful home in the fabulous Florida Keys!<.......

4 Bedrooms - Sleeps 8
Vacation Rental in Islamorada

Private Vacation Home in Islamorada

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, along with two bedrooms, both with en-suite bathrooms. All you'll need is your toothbrush and a swimsuit, and you're all set for a fabulous Florida Keys v.......

4.8 Star Review

Private Vacation Home in Islamorada

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: chairs and tables on balcony, printer, tiki hut by pool, and undercover parking.
If booking more than a year in advance current prices may not re.......

3.3 Star Review

Private Vacation Home in Islamorada

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 master suite offers breathtaking ocean views, a spacious walk-in closet and a bathroom with a shower and jacuzzi tub that will make you feel like royal.......

4.9 Star Review

Villa in Islamorada

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, seperate work and entertainment areas, smart-tv’s, water and elec by the dock, plenty of parking for vehicles and trailers.

Specifics: Downst.......

5.0 Star Review

Private Vacation Home in Islamorada

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 with the private community swimming pool, and walking proximity to the best and most popular restaurants in the Keys and many other incredible wildlife .......

4.9 Star Review

Cottage in Islamorada

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 with the convenience of being minutes away from some of the best dining and outdoor activities in the Florida Keys. Relax in our 1940's "Old Florid.......

4.9 Star Review

Private Vacation Home in Islamorada

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 2019) 70ft deep water dock (very rare for a open water home) with fish cleaning station, and fresh water and lights.
-Brand New White Kitchen with.......

4.9 Star Review

Private Vacation Home in Islamorada

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. Sleeps up to 8 - oversized master bedroom w/ one king bed, TV, walk-in closet and loft access with 2 twin beds. Second bedroom includes 2 double beds .......

4.9 Star Review

Condo in Islamorada

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. "Sunrise Haven," our Atlantic Ocean beach front condo is located near the heart of Islamorada at Mile Marker 80.6 on the quiet, less traveled, Old Federal Hi.......

4.9 Star Review

Private Vacation Home in Islamorada

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 offers a 70' concrete dock for your boat, a beautiful freshwater heated swimming pool, davits, fish cleaning table, 2 outdoor showers, gas grill, hammock, .......

5.0 Star Review