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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 Aug
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4.88 out of 5 average rating, 182 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, 123 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
6 bedrooms, 8 beds, 6.5 bathrooms
1–8 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Key West
Turtle Nest Condo + Pool
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
New place to stay
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
4.92 out of 5 average rating, 113 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
11–16 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.97 out of 5 average rating, 201 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 10 beds, 6 bathrooms
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
11–16 Jul
New place to stay
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds, 1 bathroom
21–26 Jul
4.87 out of 5 average rating, 585 reviews
Top guest favourite
Home in Marathon
Spacious 3Br/3Ba, 70ft Dock, Beach VACA23-16
3 bedrooms, 5 beds, 3 bathrooms
1–8 Aug
4.95 out of 5 average rating, 201 reviews
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
5.0 out of 5 average rating, 76 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 20 reviews
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 122 reviews
Superhost
Tiny home in Big Pine Key
Tiny Fish Haus
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Jul
4.89 out of 5 average rating, 104 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
22–29 Aug
New place to stay
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews