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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
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 74 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 32 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
12–17 Aug
4.8 out of 5 average rating, 83 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, 34 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 127 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
8–13 Aug
4.56 out of 5 average rating, 25 reviews
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 Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 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
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
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.88 out of 5 average rating, 41 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.89 out of 5 average rating, 619 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.9 out of 5 average rating, 243 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, 45 reviews