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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
3 bedrooms, 6 beds, 2 private bathrooms
6–11 Sept
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4.58 out of 5 average rating, 103 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
4–9 Aug
4.56 out of 5 average rating, 25 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
3–8 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.95 out of 5 average rating, 115 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 73 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
4.96 out of 5 average rating, 54 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 10 beds, 6 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Casa particular in Summerland Key
The Retiro House
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
12–17 Aug
4.79 out of 5 average rating, 82 reviews
Home in Summerland Key
Paraiso
3 bedrooms, 2 beds, 2 bathrooms
14–19 Aug
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 bed, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
4.94 out of 5 average rating, 89 reviews
Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds, 2 bathrooms
14–19 Aug
4.91 out of 5 average rating, 117 reviews