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Search results; Over 1,000 homes

Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 private bathroom
1–6 Aug
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4.88 out of 5 average rating, 182 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Guest favourite
Home in Little Torch Key
Sterling Bay House
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
8–15 Aug
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 53 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
20–27 Jul
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
4.91 out of 5 average rating, 554 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
Superhost
Home in Key West
Poolside Paradise
New place to stay, 3 bedrooms, 6 beds, 3 bathrooms
15–20 Aug
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
25 Jul – 1 Aug
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Hotel room in Little Torch Key
Tropical Escape w/ Kitchen, Breakfast & Pool!
2 bedrooms, 1 bathroom
21–26 Jul
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
7–12 Aug
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
29 Aug – 5 Sept
Superhost
Villa in Little Conch Key
Seapalm island | Private beach and oceanside dock
4.84 out of 5 average rating, 74 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
30 Aug – 4 Sept
Featured hotel
Hotel in Summerland Key
King room
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bathroom
21–26 Jul
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.87 out of 5 average rating, 124 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug