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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
14–19 Sept
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4.89 out of 5 average rating, 184 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 5 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
9–14 Sept
4.8 out of 5 average rating, 71 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 84 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 reviews
Featured hotel
Room in Key West
Ocean view one king bed accessible
1 bathroom
14–19 Sept
New place to stay
Featured hotel
Room in Key West
Havana king room
2 king beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Key West
King city single room
1 bedroom, 1 king bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
1–8 Nov
4.95 out of 5 average rating, 20 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.56 out of 5 average rating, 25 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 42 reviews
Superhost
Home in Sugarloaf Key
Mi Azucar
2 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
4.81 out of 5 average rating, 175 reviews
Top guest favourite
Home in Marathon
Luxury Oasis, Pool, Kayaks, Dock, Near Beach
3 bedrooms, 5 beds, 3 bathrooms
13–20 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
13–20 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
3 bedrooms, 2.5 bathrooms
23–30 Sept
4.98 out of 5 average rating, 40 reviews