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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
Guest favorite
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
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bath
Aug 16 – 21
4.8 out of 5 average rating, 85 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
4.94 out of 5 average rating, 77 reviews
Guest favorite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bath
Aug 22 – 27
4.93 out of 5 average rating, 127 reviews
Top guest favorite
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
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
Top guest favorite
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 favorite
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 favorite
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
Guest favorite
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 favorite
Tiny home 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 favorite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 baths
Aug 24 – 29
4.86 out of 5 average rating, 7 reviews
Superhost
Condo in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bath
Aug 12 – 17
5.0 out of 5 average rating, 5 reviews
Guest favorite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 baths
Sep 5 – 10
4.76 out of 5 average rating, 21 reviews
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
1 bedroom, 2 queen beds, 1 bath
Aug 18 – 23
4.71 out of 5 average rating, 134 reviews
Guest favorite
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 favorite
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
Guest favorite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 baths
Sep 26 – Oct 1
4.83 out of 5 average rating, 111 reviews