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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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4.89 out of 5 average rating, 183 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 616 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 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 Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 1 bathroom
21–26 Jul
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
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
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.87 out of 5 average rating, 125 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Hotel room in Little Torch Key
Island Escape, Pool, Breakfast + Private Beach!
1 bedroom, 1 bathroom
10–15 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 202 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Top guest favourite
Home in Cudjoe Key
Oceanside home 109, dock,kayaks,bikes,pool,fishing
4.94 out of 5 average rating, 32 reviews, 2 bedrooms, 3 beds, 3 bathrooms
21–26 Jul
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
4.97 out of 5 average rating, 124 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 98 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
22–29 Jul
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
4.78 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 4 beds, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Flat in Marathon
Waterfront Retreat | Marina Views & Pool
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Jul