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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
19–24 Sept
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4.86 out of 5 average rating, 42 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 10 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
13–18 Sept
4.81 out of 5 average rating, 72 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 92 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.94 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 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, 16 reviews
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.89 out of 5 average rating, 185 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 49 reviews
Featured hotel
Rooms in Marathon
Gulf view suite
2 bedrooms, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
25–30 Oct
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
14–19 Nov
4.83 out of 5 average rating, 12 reviews
Luxe
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
12–17 Sept
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
13–18 Oct
4.95 out of 5 average rating, 39 reviews
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
New place to stay
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 43 reviews
Featured hotel
Room in Key West
Havana king room
2 king beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 4 reviews