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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 Aug
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4.93 out of 5 average rating, 387 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
New place to stay, 4 bedrooms, 4 beds, 4 bathrooms
3–9 Aug
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
4.96 out of 5 average rating, 69 reviews, 3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 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
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
5.0 out of 5 average rating, 54 reviews, 4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
Top guest favourite
Home in Islamorada
Flakey's
4.97 out of 5 average rating, 216 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–15 Aug
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
New place to stay, 7 bedrooms, 7 beds, 7 bathrooms
17–22 Aug
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 1 bed, 3 bathrooms
9–14 Aug
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 3 bathrooms
7–14 Aug
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
2–9 Aug
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds, 3 bathrooms
8–15 Aug
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Aug
Home in Islamorada
Charming Beach House directly ON the beach
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 6 beds, 3 bathrooms
17–24 Aug
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
4.95 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
23–30 Aug
Guest favourite
Home in Key Colony Beach
4/2.5 Waterfront home on Key Colony, Pool, Dockage
4.85 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–21 Aug
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
4.87 out of 5 average rating, 179 reviews, 3 bedrooms, 10 beds, 3 bathrooms
11–16 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