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Search results; Over 1,000 homes in Summerland Key

Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 private bathroom
13–18 Sept
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4.93 out of 5 average rating, 127 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
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
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
Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 8 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 Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 55 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
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
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
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 Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
New place to stay
Guest favourite
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.88 out of 5 average rating, 132 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.83 out of 5 average rating, 112 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
25–30 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Cudjoe Key
105- Newly renovated house with ocean view & pool
2 bedrooms, 2 king beds, 3 bathrooms
15–20 Sept
4.88 out of 5 average rating, 16 reviews
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews