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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, 184 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
9–14 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, 5 bathrooms
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, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
9–14 Sept
4.81 out of 5 average rating, 72 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
Havana 2 queens
2 queen beds, 1 bathroom
9–14 Sept
Featured hotel
Room in Key West
Queen Room
1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 14 reviews
Featured hotel
Room in Key West
Ocean view one king bed
1 bathroom
15–20 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.89 out of 5 average rating, 103 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 Sept
4.88 out of 5 average rating, 132 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
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
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, 5 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
Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
New place to stay
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
4.83 out of 5 average rating, 12 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 33 reviews