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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
9–14 Jul
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4.93 out of 5 average rating, 385 reviews
Guest favourite
Home in Islamorada
Islamorada Bungalow # 5
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.86 out of 5 average rating, 35 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
25 Jul – 1 Aug
4.97 out of 5 average rating, 214 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
9–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 13 reviews
Home in Islamorada
Margaritaville
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
5–12 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
9–15 Aug
4.97 out of 5 average rating, 31 reviews
Guest favourite
Flat in Tavernier
Panoramic Ocean Views, Ocean Pointe Condo
2 bedrooms, 2 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Tavernier
Marina & Ocean Front Suite 5202
2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Key Largo
Villa Nueva
3 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 25 reviews
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
3 bedrooms, 3 beds, 3 bathrooms
14–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Key Largo
Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
5 bedrooms, 9 beds, 3 bathrooms
3–8 Aug
4.99 out of 5 average rating, 151 reviews
Guest favourite
Apartment in Key Largo
Gorgeous lagoon-front 2BR Townhouse with 2 pools
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.91 out of 5 average rating, 161 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
4–11 Sept
5.0 out of 5 average rating, 52 reviews
Guest favourite
Home in Islamorada
FL Keys Ocean Front Escape
2 bedrooms, 2 beds, 3 bathrooms
6–13 Jul
4.9 out of 5 average rating, 10 reviews
Guest favourite
Flat in Tavernier
Welcome to the Pelican Lodge !
2 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.91 out of 5 average rating, 33 reviews
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed, 1 bathroom
13–18 Jul
New place to stay