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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 Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
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
1–8 Aug
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 51 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 112 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 553 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.54 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
Featured hotel
Hotel in Summerland Key
King room
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bathroom
5–10 Jul
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
New place to stay, 5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4.97 out of 5 average rating, 145 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 4 beds, 2 bathrooms
25 Aug – 1 Sept
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 27 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
19–26 Sept
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 38 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Superhost
Home in Big Pine Key
Keys Beach Retreat Close to Key West
4.8 out of 5 average rating, 20 reviews, 3 bedrooms, 6 beds, 2 bathrooms
17–22 Aug
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 84 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug