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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 Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.95 out of 5 average rating, 115 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
8–15 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 618 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 127 reviews
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 83 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 43 reviews
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
1 bedroom, 2 king beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 33 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 73 reviews
Top guest favourite
Home in Cudjoe Key
Aug. Discount, Waterfront Retreat/Pool/golf cart
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Flat in Big Pine Key
New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5
2 bedrooms, 2 beds, 1 bathroom
26–31 Aug
4.94 out of 5 average rating, 64 reviews
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
4.94 out of 5 average rating, 89 reviews
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
3–10 Aug
Guest favourite
Home in Cudjoe Key
Waterfront 2BR w/ Dock & Pool Access
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.86 out of 5 average rating, 29 reviews
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.97 out of 5 average rating, 126 reviews