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Search results; Over 1,000 homes in Summerland Key

Guest favourite
Home in Sugarloaf Key
The Guest House - Sugarloaf Beach Key West
2 bedrooms, 7 beds, 2.5 private bathrooms
9–14 Aug
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4.82 out of 5 average rating, 131 reviews
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
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
3–8 Aug
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Superhost
Tiny home in Summerland Key
Cottage
4.93 out of 5 average rating, 70 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 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
31 Jul – 5 Aug
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 10 beds, 6 bathrooms
7–12 Sept
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 Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 98 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
5.0 out of 5 average rating, 41 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
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 Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 202 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Cudjoe Key
Aug. Discount, Waterfront Retreat/Pool/golf cart
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
4.97 out of 5 average rating, 124 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
4.94 out of 5 average rating, 88 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
4.94 out of 5 average rating, 176 reviews, 2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
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
5–10 Sept