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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
18–23 Sept
,
4.89 out of 5 average rating, 185 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
16–21 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
15–20 Sept
4.96 out of 5 average rating, 55 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
16–23 Sept
5.0 out of 5 average rating, 5 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
4.81 out of 5 average rating, 74 reviews
Featured hotel
Hotel in Marathon
Gulf view suite
2 bedrooms, 1 bathroom
27 Sept – 2 Oct
Luxe
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
15–20 Sept
4.56 out of 5 average rating, 25 reviews
Top guest favourite
Home in Marathon
Paradise in the Keys
3 bedrooms, 8 beds, 2 bathrooms
15–22 Sept
4.95 out of 5 average rating, 38 reviews
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
8–15 Dec
4.95 out of 5 average rating, 20 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
New place to stay
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
New place to stay
Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.99 out of 5 average rating, 75 reviews
Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
4.92 out of 5 average rating, 97 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, 50 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.91 out of 5 average rating, 75 reviews