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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key
Powell Family Resort
6 bedrooms, 7 beds, 3 private bathrooms
15–20 Aug
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4.86 out of 5 average rating, 42 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 32 reviews, 1 bedroom, 3 beds, 1 bathroom
3–8 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
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 4 beds, 1 bathroom
1–6 Aug
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Superhost
Tiny home in Summerland Key
Cottage
4.93 out of 5 average rating, 73 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 115 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, 54 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Summerland Key
Private Pool Oasis | 3 King Suites | 30 Min to KW
4.84 out of 5 average rating, 62 reviews, 3 bedrooms, 4 beds, 3 bathrooms
1–6 Aug
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
5.0 out of 5 average rating, 9 reviews, 6 bedrooms, 10 beds, 6 bathrooms
7–12 Sept
Superhost
Tiny home in Summerland Key
Bungalow
4.8 out of 5 average rating, 80 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 101 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Superhost
Home in Key West
Fleming Street 2/1 private home Key West getaway
4.91 out of 5 average rating, 135 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Aug
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
4.94 out of 5 average rating, 89 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
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
Home in Cudjoe Key
Heron House
2 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug