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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
4.81 out of 5 average rating, 37 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 215 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
4.93 out of 5 average rating, 387 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 33 reviews, 3 bedrooms, 3 bathrooms
9–15 Aug
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4.87 out of 5 average rating, 46 reviews, 4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Guest favourite
Townhouse in Key Largo
Sunrise Retreat: Ocean & Pool Views, Gym, PB Court
4.89 out of 5 average rating, 65 reviews, 3 bedrooms, 5 beds, 3 bathrooms
17–22 Aug
Guest favourite
Apartment in Tavernier
Condo in Tavernier
4.96 out of 5 average rating, 49 reviews, 2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
4.82 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
5.0 out of 5 average rating, 103 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
14–21 Jul
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
New place to stay, 2 beds, 1 bathroom
20–25 Jul
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 52 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 75 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
4.96 out of 5 average rating, 147 reviews, 2 bedrooms, 3 beds, 1 bathroom
22–27 Aug