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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
3 bedrooms, 6 beds, 2 private baths
Sep 6–11
,
4.55 out of 5 average rating, 104 reviews
Superhost
Tiny homes in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bath
Aug 14–19
4.94 out of 5 average rating, 77 reviews
Superhost
Tiny homes in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bath
Aug 16–21
4.8 out of 5 average rating, 85 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bath
Aug 23–28
4.97 out of 5 average rating, 33 reviews
Guest favourite
Condo in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bath
Aug 16–21
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds, 2 baths
Aug 16–21
4.95 out of 5 average rating, 116 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 baths
Aug 20–25
4.56 out of 5 average rating, 25 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 2 baths
Aug 16–21
4.96 out of 5 average rating, 54 reviews
Top guest favourite
Casa particular in Summerland Key
The Retiro House
3 bedrooms, 4 beds, 2 baths
Aug 31–Sep 5
5.0 out of 5 average rating, 9 reviews
Guest favourite
Tiny homes in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bath
Aug 23–28
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 baths
Sep 25–30
5.0 out of 5 average rating, 14 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 baths
Sep 7–12
5.0 out of 5 average rating, 10 reviews
Superhost
Condo in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bath
Aug 13–18
5.0 out of 5 average rating, 5 reviews
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bath
Aug 13–18
4.89 out of 5 average rating, 183 reviews
Guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bath
Sep 27–Oct 2
4.92 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bath
Aug 15–20
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 baths
Nov 15–20
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds, 1 bath
Sep 13–18
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 baths
Aug 30–Sep 4
5.0 out of 5 average rating, 10 reviews