Vacation rentals in Islamorada
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Top-rated vacation rentals in Islamorada
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
Waterfront Conch Cottage. Short walk to world famous Lorelei for sunset celebrations. Custom length of stays can be arranged if booking a sandbar/sunset/fishing charter with our family business. The cottage was built in 1940s and still has the original hardwood floors, open beam ceilings. Private yet in the heart of Islamorada. Walk to two local craft breweries nearby! This listing is new to AIRBNB but booked for many reservations thru VRBO all 5 star. One pet only under 20lbs. /pet fee $150
Sep. 5 – 12
Apartment in Tavernier
4.95 out of 5 average rating, 144 reviewsCapt Craigs 1 Bedroom /1 Bath Apartment
Capt. Craig’s Guest Quarters The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.
Dec. 6 – 13
Guesthouse in Key Largo
4.87 out of 5 average rating, 370 reviewsGuesthouse/Cabin peaceful romantic *sunsets beach.
Guesthouse/Cabin romantic *sunsets beach, docks and fishing pier, on a peaceful lush gardens with private parking to enjoy and relax, surrounded by nature wildlife at its best birds, iguanas, manatees, dolphin’s, eagles only a short walk to the beach and fishing pier, enjoy the immense boats cruising by, relax sipping cocktail. Note a "guesthouse" is part as on a state, small separate dwelling on the grounds of a larger one, used for accommodating guests. *the guesthouse is Not beachfront.
Jun. 4 – 11
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Islamorada vacation rentals
Other great vacation rentals in Islamorada
Home in Key Largo
5.0 out of 5 average rating, 43 reviewsThe Paradise 2
Feb. 2 – 9
Cottage in Islamorada
4.97 out of 5 average rating, 63 reviewsIslamorada 2BR, 1BA w/ heated pool and firepit
Aug. 5 – 12
Cottage in Islamorada
4.94 out of 5 average rating, 36 reviewsIslamorada bungalow 2 bed & pool
Oct. 23 – 30
Home in Islamorada
5.0 out of 5 average rating, 5 reviewsAnglers Reef Home with Peek-a-Boo Ocean Views
May 13 – 20
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
Nov. 9 – 16
Home in Islamorada
4.93 out of 5 average rating, 14 reviews3 Lux Ensuites Walk/Boat Island!
Jan. 18 – 25
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
Oct. 12 – 19
Home in Key Largo
4.99 out of 5 average rating, 69 reviewsLittle Cottage on an island
Jun. 17 – 24
Home in Islamorada
5.0 out of 5 average rating, 29 reviewsAnglers Reef Islamorada Oceanside 2/2.5+Pool+Beach
Jun. 8 – 15
Home in Islamorada
4.96 out of 5 average rating, 55 reviewsTropical Getaway 3/3 with 100’ boat dock and pool
Sep. 17 – 24
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
Jun. 8 – 15
Tiny homes in Key Largo
4.98 out of 5 average rating, 57 reviewsOceanfront Lookout Point w/two Kayaks & Deck
Oct. 4 – 11
Quick stats about vacation rentals in Islamorada
Total rentals | 810 properties |
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Rentals with a pool | 630 properties have a pool |
Pet-friendly rentals | 400 properties allow pets |
Family-friendly rentals | 580 properties are a good fit for families |
Total number of reviews | 5.6K reviews |
Nightly prices starting at | $54 CAD before taxes and fees |
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