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Search results; Over 1,000 homes in Summerland Key

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Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
1 bedroom, 3 beds, 1 private bathroom
1–6 Sept
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4.77 out of 5 average rating, 92 reviews
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Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds
13–18 Sept
4.93 out of 5 average rating, 127 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
6–11 Sept
4.94 out of 5 average rating, 80 reviews
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Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds
30 Sept – 5 Oct
4.94 out of 5 average rating, 36 reviews
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Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds
6–11 Sept
4.81 out of 5 average rating, 91 reviews
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
1–6 Sept
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 8 reviews
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Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 208 reviews
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Superhost
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds
7–12 Sept
5.0 out of 5 average rating, 12 reviews
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Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
7–12 Sept
4.56 out of 5 average rating, 25 reviews
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Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
9–14 Nov
4.88 out of 5 average rating, 8 reviews
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Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms, 16 beds
7–12 Sept
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Cudjoe Key
Betty's Place
2 bedrooms, 3 beds
18–23 Sept
4.92 out of 5 average rating, 119 reviews
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Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
20–25 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 8 reviews
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Superhost
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.89 out of 5 average rating, 103 reviews
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Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds
9–14 Sept
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Guest favourite
Home in Cudjoe Key
Relaxing Home in the Keys
2 bedrooms, 2 beds
1–6 Sept
4.88 out of 5 average rating, 58 reviews