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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 Sept
,
4.89 out of 5 average rating, 183 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 127 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
23–30 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds, 5 bathrooms
25–30 Sept
4.89 out of 5 average rating, 84 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.89 out of 5 average rating, 619 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.88 out of 5 average rating, 129 reviews
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 179 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
4.89 out of 5 average rating, 157 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
4.94 out of 5 average rating, 78 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 207 reviews
Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed, 2 bathrooms
17–22 Aug
4.92 out of 5 average rating, 53 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.88 out of 5 average rating, 42 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, 45 reviews
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
21–26 Aug
4.94 out of 5 average rating, 34 reviews