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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
,
4.88 out of 5 average rating, 182 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
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
1–8 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
8–13 Aug
4.96 out of 5 average rating, 51 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds
8–13 Aug
4.95 out of 5 average rating, 112 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed
3–8 Aug
4.91 out of 5 average rating, 553 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds
11–18 Aug
New place to stay
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
2–7 Aug
4.54 out of 5 average rating, 24 reviews
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds
11–18 Jul
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 37 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Awai's Floating Villa
2 bedrooms, 2 queen beds
6–11 Jul
4.93 out of 5 average rating, 83 reviews
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds
25 Aug – 1 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds
15–22 Aug
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
12–17 Jul
5.0 out of 5 average rating, 38 reviews
Superhost
Villa in Little Conch Key
Seapalm island | Private beach and oceanside dock
5 bedrooms, 6 beds
30 Aug – 4 Sept
4.84 out of 5 average rating, 74 reviews
Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds
5–10 Jul
4.92 out of 5 average rating, 113 reviews