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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
17–22 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
8 bedrooms, 15 beds
27 Sept – 2 Oct
4.89 out of 5 average rating, 84 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds
14–19 Sept
4.93 out of 5 average rating, 127 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds
16–23 Sept
5.0 out of 5 average rating, 5 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds
14–19 Sept
New place to stay
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds
25–30 Oct
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.89 out of 5 average rating, 103 reviews
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds
8–15 Dec
4.95 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds
28 Nov – 5 Dec
5.0 out of 5 average rating, 3 reviews
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds
14–19 Sept
4.88 out of 5 average rating, 132 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds
14–19 Nov
4.83 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
27 Oct – 1 Nov
4.88 out of 5 average rating, 43 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds
14–19 Sept
4.81 out of 5 average rating, 73 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds
20–25 Sept
4.86 out of 5 average rating, 616 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
1–6 Dec
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 6 reviews