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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 Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 113 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Superhost
Home in Cudjoe Key
Ocean~View w/ Dock, Pool, Kayaks, King Bed
4.92 out of 5 average rating, 92 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
4.99 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 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
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
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
Guest favourite
Home in Cudjoe Key
Waterfront Sanctuary in the Keys!
4.88 out of 5 average rating, 155 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 29 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
4.94 out of 5 average rating, 175 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
4.97 out of 5 average rating, 86 reviews, 2 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 2.5 bathrooms
15–22 Sept
Top guest favourite
Home in Marathon
Sombrero beach vacation paradise, great location
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 7 beds, 2 bathrooms
17–24 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
Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
4.91 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 612 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul