filters

Search results; Over 1,000 homes in Summerland Key

Photo 1 of 6
Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
1 bedroom, 3 beds, 1 private bathroom
1–6 Sept
,
4.77 out of 5 average rating, 92 reviews
Photo 1 of 6
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 80 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.81 out of 5 average rating, 91 reviews
Photo 1 of 6
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.94 out of 5 average rating, 36 reviews
Photo 1 of 6
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 10 reviews
Photo 1 of 6
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 36 reviews
Photo 1 of 6
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, 15 reviews
Photo 1 of 6
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
Photo 1 of 6
Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 208 reviews
Photo 1 of 6
Superhost
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, 12 reviews
Photo 1 of 6
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
4.56 out of 5 average rating, 25 reviews
Photo 1 of 6
Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.92 out of 5 average rating, 97 reviews
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.88 out of 5 average rating, 8 reviews
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
8–13 Jan
4.83 out of 5 average rating, 111 reviews
Photo 1 of 6
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.97 out of 5 average rating, 129 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 47 reviews
Photo 1 of 6
Featured hotel
Room in Key West
One queen bed
1 bathroom
6–11 Sept
4.83 out of 5 average rating, 23 reviews
Photo 1 of 6
Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms, 16 beds, 9 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 reviews