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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
12–17 Sept
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4.54 out of 5 average rating, 105 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
10–15 Sept
4.94 out of 5 average rating, 81 reviews
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds
13–18 Sept
4.82 out of 5 average rating, 92 reviews
Featured hotel
Hotel in Summerland Key
King room
1 bedroom, 1 king bed
9–14 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4 bedrooms, 6 beds
16–21 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
9–14 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
3 bedrooms, 6 beds
14–19 Sept
4.96 out of 5 average rating, 55 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 16 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds
9–14 Sept
4.81 out of 5 average rating, 72 reviews
Featured hotel
Room in Key West
Havana king room
2 king beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds
25–30 Oct
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
13–18 Oct
4.95 out of 5 average rating, 39 reviews
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
10–15 Sept
4.56 out of 5 average rating, 25 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
11–16 Sept
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Cudjoe Key
Keys Island Villa - Venture Out Home 354
2 bedrooms, 2 beds
9–14 Sept
4.95 out of 5 average rating, 92 reviews
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds
13–18 Sept
4.88 out of 5 average rating, 42 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Oct
4.96 out of 5 average rating, 211 reviews