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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 bathrooms
1–6 Aug
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4.57 out of 5 average rating, 101 reviews
Guest favourite
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 58 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
8–13 Jul
4.97 out of 5 average rating, 33 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
3–8 Aug
4.78 out of 5 average rating, 74 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 200 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 Sept
4.96 out of 5 average rating, 85 reviews
Home in Key West
Family friendly-Waterfront retreat
4 bedrooms, 7 beds, 2 bathrooms
7–12 Aug
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
31 Jul – 5 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 74 reviews
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Cudjoe Key
King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!
2 bedrooms, 3 beds, 2 bathrooms
28 Aug – 2 Sept
4.94 out of 5 average rating, 175 reviews
Guest favourite
Home in Big Pine Key
Cozy house with relaxing pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.75 out of 5 average rating, 8 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
4.87 out of 5 average rating, 38 reviews
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
4.88 out of 5 average rating, 182 reviews
Guest favourite
Home in Cudjoe Key
Relaxing Home in the Keys
2 bedrooms, 2 beds, 1 bathroom
21–26 Jul
4.88 out of 5 average rating, 56 reviews
Guest favourite
Home in Cudjoe Key
Blue Heaven Waterfront Home
2 bedrooms, 3 beds, 2 bathrooms
15–22 Aug
4.88 out of 5 average rating, 17 reviews
Holiday home in Cudjoe Key
Crystal Clear Canal Front 2/1 on Cudjoe Key!
2 bedrooms, 3 beds, 1 bathroom
18–23 Jul
4.71 out of 5 average rating, 82 reviews