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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
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4.89 out of 5 average rating, 185 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
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
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 5 reviews
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 10 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
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
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.88 out of 5 average rating, 132 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
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
10–15 Sept
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
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds, 2 bathrooms
28 Nov – 5 Dec
5.0 out of 5 average rating, 3 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, 49 reviews
Guest favourite
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
13–20 Sept
4.94 out of 5 average rating, 205 reviews
Top guest favourite
Home in Cudjoe Key
Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Cudjoe Key
Tiki Time in Cudjoe Key 136
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 59 reviews