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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Jul
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4.97 out of 5 average rating, 94 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, 36 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
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
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, 14 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
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 385 reviews
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
31 Jul – 5 Aug
4.83 out of 5 average rating, 112 reviews
Guest favourite
Apartment in Tavernier
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
2 bedrooms, 4 beds, 2 bathrooms
9–14 Jul
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
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
Home in Islamorada
Island Paradise in Anglers Reef!
2 bedrooms, 3 beds, 2.5 bathrooms
11–18 Jul
5.0 out of 5 average rating, 5 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
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, 32 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
Top guest favourite
Flat in Tavernier
Marina & Ocean Front Suite 5202
2 bedrooms, 4 beds, 2 bathrooms
9–14 Jul
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
5.0 out of 5 average rating, 76 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