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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
12–17 Aug
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4.89 out of 5 average rating, 183 reviews
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 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
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 617 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, 115 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.87 out of 5 average rating, 126 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 100 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
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
Featured hotel
Hotel in Summerland Key
King room
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 1 bathroom
6–11 Aug
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 Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 204 reviews, 2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
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
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 32 reviews, 1 bedroom, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.97 out of 5 average rating, 37 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
Aug. Discount, Waterfront Retreat/Pool/golf cart
4.97 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Home in Cudjoe Key
101- Oceanside House with Pool
4.89 out of 5 average rating, 258 reviews, 2 bedrooms, 2 beds, 3 bathrooms
1–6 Aug
Guest favourite
Cottage in Cudjoe Key
2Bd/1Ba Waterfront Retreat w/35’ Dock
4.84 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Aug