filters

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
,
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
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
22–27 Aug
4.93 out of 5 average rating, 122 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 Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 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
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
Home in Summerland Key
Paraiso
3 bedrooms, 2 beds, 2 bathrooms
8–13 Jul
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
Home in Cudjoe Key
Comfortable Home w/ Amenities in Gated Community
2 bedrooms, 3 beds, 1 bathroom
2–7 Jul
4.67 out of 5 average rating, 9 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 10 beds, 6 bathrooms
16–21 Aug
5.0 out of 5 average rating, 8 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 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
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
14–19 Jul
4.89 out of 5 average rating, 609 reviews
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
1 bedroom, 2 queen beds, 1 bathroom
5–10 Jul
4.72 out of 5 average rating, 123 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
New Construction. $299 per night.
2 bedrooms, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cottage in Cudjoe Key
2Bd/1Ba Waterfront Retreat w/35’ Dock
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Aug
4.83 out of 5 average rating, 30 reviews