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
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed
1–6 Sept
5.0 out of 5 average rating, 10 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
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
6–11 Sept
4.81 out of 5 average rating, 91 reviews
Photo 1 of 6
Featured hotel
Room in Key West
Ocean view one king bed accessible
7–12 Sept
New place to stay
Photo 1 of 6
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
Photo 1 of 6
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds
7–12 Sept
4.95 out of 5 average rating, 116 reviews
Photo 1 of 6
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
14–19 Sept
4.96 out of 5 average rating, 55 reviews
Photo 1 of 6
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
Photo 1 of 6
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds
1–6 Sept
4.89 out of 5 average rating, 184 reviews
Photo 1 of 6
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
Photo 1 of 6
Superhost
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds
5–10 Sept
4.89 out of 5 average rating, 18 reviews
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds
13–18 Sept
4.88 out of 5 average rating, 42 reviews
Photo 1 of 6
Top guest favourite
Home in Marathon
70ft Dock, Bikes, Beach, Spacious, VACA23-16
3 bedrooms, 5 beds
13–20 Sept
4.94 out of 5 average rating, 204 reviews
Photo 1 of 6
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
Photo 1 of 6
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
Photo 1 of 6
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds
7–12 Sept
4.8 out of 5 average rating, 69 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
1–6 Sept
5.0 out of 5 average rating, 47 reviews
Photo 1 of 6
Superhost
Home in Cudjoe Key
Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks
2 bedrooms, 4 beds
12–17 Sept
4.92 out of 5 average rating, 97 reviews