filters

Search results; Over 1,000 homes in Summerland Key

Photo 1 of 29
Top guest favourite
Home in Summerland Key
Ocean front classic keys cottage
3 bedrooms, 5 beds, 2 bathrooms
8–15 Dec
4.95 out of 5 average rating, 20 reviews
Photo 1 of 18
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 82 reviews
Photo 1 of 18
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 94 reviews
Photo 1 of 24
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 116 reviews
Photo 1 of 29
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 37 reviews
Photo 1 of 29
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
Photo 1 of 25
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 55 reviews
Photo 1 of 29
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 16 reviews
Photo 1 of 29
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 29
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
4.96 out of 5 average rating, 212 reviews
Photo 1 of 29
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, 13 reviews
Photo 1 of 29
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
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
Photo 1 of 6
Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 621 reviews
Photo 1 of 6
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 19 reviews
Photo 1 of 29
Guest favourite
Home in Cudjoe Key
Oceanfront 2BR in Venture Out - 35’ Dock + Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 18 reviews
Photo 1 of 29
Home in Cudjoe Key
Private Secluded Ocean View & Pool Near Key West
4 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
New place to stay
Photo 1 of 29
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 51 reviews