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Islamorada Vacation Rentals, Beach Houses and Condos for Rent

Book Your Islamorada, FL Florida Vacation Rental Homes Here and Save! Many to choose from!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Islamorada, FL, Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals in Islamorada, FL to choose from, we now have the selection and value to offer our visitors going to Florida.

Listings

Lodge Sol at La Jolla Resort

3 Bedroom Private Oceanfront House - Sol

Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise loung.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Islamorada House Rental

Details


Executive Bay Club R-6

Executive Bay Club R-6 - Wonderful 2 Bedroom Condo in Great Location

Wonderful condo in Islamorada's gated bayfront complex. Executive Bay Club is comprised of town homes with bayfront beach access, tennis, clubhouse, fishing pier and swimming pool. Fabulous location right next to Founder's Park that offers an olympic size pool, splash pad and play ground for the kids, quiet beach, tennis and sporting fields. The t.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Islamorada Condo Rental

Details


194 Airstream Lane

Stunning 3 Bedroom Bayfront Home - 194 Airstream Lane

The most spectacular bay views from this stunning Islamorada home. This newly remodeled home offers 3 bedrooms and 2 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 kayaks, bikes, a summer ki.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 Islamorada House Rental

Details


132 Atlantic Lane

Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Atlantic Ln.

Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 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 dining room tabl.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Islamorada House Rental

Details


Vacation Rental

Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.

Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and private dock, close to the best restaurants, and sight seeing. Peaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a bo.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 Islamorada House Rental

Details


Lodge Bahia at La Jolla Resort

4 Bedroom Private Oceanfront House - Bahia

Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise loung.......read more

4 Bedroom(s)
2 Bath(s) - Sleeps 8 Islamorada House Rental

Details


141 Ocean Lane

2 Bedroom Home with Ocean Views and Canal Dockage - 141 Ocean Ln.

"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 degree view of th.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Islamorada House Rental

Details


Ocean Harbour K-44

Ocean Harbour K-44 - Oceanfront 2 Bedroom Condo with Contemporary Flair

Islamorada's Desirable Ocean Harbour Condominium Complex. Remodeled two bedroom two bath unit with a contemporary flair. Fabulous location with gorgeous unobstructed ocean views. Screened balcony lets you enjoy the beauty of Ocean Harbour and the serene blue Atlantic Ocean. Twelve professionally landscaped and gated acres at oceans's edge includes .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Islamorada Condo Rental

Details


120 Cortez Drive Unit A

120 Cortez Drive Unit A

Get ready to Live and Play in this awesome Oceanside 2 bedroom/2 bath townhouse which features protected dockage for up to a 25' boat. Amenities include shared pool and tennis court, wifi, washer/dryer, and cool AC. Located at the 76 mile marker, take in the quiet Islamorada breezes while being only 4 miles from local shops, fresh fish, and tiki ba.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Islamorada Townhome Rental

Details


Turtle Cove

Turtle Cove - Oceanfront Estate with 4 Cozy Cottages

Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that makes you realize your vacation has started. Each cottage has .......read more

7 Bedroom(s)
7 Bath(s) - Sleeps 16 Islamorada Estate Rental

Details


Windy Cove #3

Great 3 Bedroom Oceanfront Town Home with Pool - Windy Cove #3

Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 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 a palm tree, or wake .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Islamorada Townhome Rental

Details


Beach Dream House

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun rising over the Atlantic Ocean and superb views from every room in the house: 360 degrees of glass and a wraparound balcony . Pool and private sandy beach. Two spacious rooms and a very large loft. The loft is a great getaway for kid.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Islamorada House Rental

Details


102 Columbus Drive

Charming 2 Bedroom Canalfront Home in Islamorada

Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large balcony on a private canal. Unwind on the porch or go swi.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Islamorada House Rental

Details


Oceanview Maison Matecumbe #306

Oceanview Maison Matecumbe #306 - Beachy 3 Bedroom Condo with Ocean Views

Maison Matecumbe is an exclusive gated and private boutique townhome complex. This wonderful unit offers an open floor and three inviting bedrooms and three baths. The master en suite has a king bed, second guest room has 2 full beds and the lower level guest room has a queen bed. Newly renovated kitchen opens up to the dining and living room. The .......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 6 Islamorada Condo Rental

Details


Angler's Retreat

Anglers Reef Islamorada home with ocean views, private marina, beach & pool

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 Bedroom(s)
3 Bath(s) - Sleeps 6 Islamorada House Rental

Details


Vacation Rental

Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream

Welcome to Paradise! This fabulous Old Florida Style home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dream! ***Ask about reduced seasonal rates Sept thru Nov! Located in a beautiful, quiet cul-de-sac, on a deep water canal with access to the community's private beach & private boat ramp is minutes by boat to the Flori.......read more

4 Bedroom(s)
4 Bath(s) - Sleeps 15 Islamorada House Rental

Details


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