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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
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4.89 out of 5 average rating, 183 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
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 Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds, 2 bathrooms
24–31 Oct
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
23–30 Aug
4.94 out of 5 average rating, 203 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 558 reviews
Guest favourite
Home in Marathon
Oceanfront Sunsets | Kayaks-Pool-Dock-Putt Green
4 bedrooms, 4 beds, 3 bathrooms
26 Aug – 2 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Villa in Little Conch Key
Seapalm island | Private beach and oceanside dock
5 bedrooms, 6 beds, 5.5 bathrooms
30 Aug – 4 Sept
4.84 out of 5 average rating, 75 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
Featured hotel
Hotel in Summerland Key
Waterview one bedroom suite
1 bedroom, 1 king bed, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 211 reviews
Top guest favourite
Villa in Marathon
The Lucky Fisherman Retreat
4 bedrooms, 7 beds, 3 bathrooms
16–23 Aug
5.0 out of 5 average rating, 5 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
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
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 4 reviews