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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
Home in Islamorada
Margaritaville
3 bedrooms, 3 beds, 2 bathrooms
5–10 Aug
4.88 out of 5 average rating, 8 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 Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
4.97 out of 5 average rating, 93 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
Guest favourite
Apartment in Tavernier
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
2 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
4.91 out of 5 average rating, 160 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 102 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
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
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
Flat in Tavernier
Marina & Ocean Front Suite 5202
2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.97 out of 5 average rating, 31 reviews
Guest favourite
Apartment in Tavernier
Condo in Tavernier
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
18–25 Jul
5.0 out of 5 average rating, 24 reviews
Guest favourite
Townhouse in Islamorada
Oceanfront Islamorada Townhome with Pool & Dock
3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Retreat: Ocean & Pool Views, Gym, PB Court
3 bedrooms, 5 beds, 3 bathrooms
23–28 Jul
4.89 out of 5 average rating, 65 reviews
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Islamorada
Keezy Dream House+Beach, Pool & Kayaks at Anglers
2 bedrooms, 3 beds, 2.5 bathrooms
7–14 Jul
4.92 out of 5 average rating, 26 reviews