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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
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
4.89 out of 5 average rating, 83 reviews, 8 bedrooms, 15 beds, 5 bathrooms
20–25 Sept
Featured hotel
Hotel in Summerland Key
Waterview one bedroom suite
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bathroom
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
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
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
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 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
26 Sept – 1 Oct
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Aug
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
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 2.5 bathrooms
15–22 Sept
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
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 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
24–29 Sept
Featured hotel
Room in Key West
Pool view one king bed accessible
New place to stay, 1 bathroom
15–20 Aug
Hotel room in Little Torch Key
Island Escape, Pool, Breakfast + Private Beach!
1 bedroom, 1 bathroom
10–15 Aug
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
New place to stay, 1 king bed, 1 bathroom
8–13 Aug
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 2 queen beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Duck Key
Private Pool Tropical Oasis - Centrally Located
5.0 out of 5 average rating, 112 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Oct