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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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4.89 out of 5 average rating, 183 reviews
Guest favourite
Home in Little Torch Key
Sterling Bay House
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 8 beds, 6.5 bathrooms
8–15 Aug
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Little Torch Key
Waterfront Beach Houses with Dock & Heated Pool!
4.89 out of 5 average rating, 83 reviews, 8 bedrooms, 15 beds, 5 bathrooms
20–25 Sept
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Superhost
Home in Big Pine Key
Private Island - The true privilege of seclusion
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
7–14 Aug
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 34 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
22–29 Aug
Top guest favourite
Home in Marathon
Oceanfront•Sunrise from Bed •Pool Spa• Near Beach
5.0 out of 5 average rating, 15 reviews, 5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
Superhost
Home in Cudjoe Key
Oceanfront with 50’ Dock & Stunning Views
New place to stay, 2 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
7–12 Aug
Featured hotel
Hotel in Summerland Key
Waterfront two bedroom cottage
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 1 bathroom
10–15 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 99 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
1–8 Aug
Superhost
Home in Little Torch Key
New House on Little Torch Key
3 bedrooms, 6 beds, 2 bathrooms
1–8 Aug
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
11–16 Aug
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 2.5 bathrooms
15–22 Sept
Top guest favourite
Holiday home in Key Colony Beach
Waterfront 4BR | Dual Living | Hot Tub | Dock
5.0 out of 5 average rating, 28 reviews, 4 bedrooms, 4 beds, 3 bathrooms
22–27 Aug