filters

Search results; Over 1,000 homes in Summerland Key

Photo 1 of 29
Home in Summerland Key
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
3 bedrooms, 6 beds, 2 private bathrooms
1–6 Oct
,
4.55 out of 5 average rating, 106 reviews
Photo 1 of 17
Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 18
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
1–6 Oct
4.94 out of 5 average rating, 82 reviews
Photo 1 of 18
Guest favourite
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds
1–6 Oct
4.82 out of 5 average rating, 96 reviews
Photo 1 of 29
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
Photo 1 of 29
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, 40 reviews
Photo 1 of 29
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
1–6 Oct
4.97 out of 5 average rating, 37 reviews
Photo 1 of 21
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp
3 bedrooms, 6 beds
12–17 Oct
4.93 out of 5 average rating, 127 reviews
Photo 1 of 29
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool
4 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 6
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 19 reviews
Photo 1 of 29
Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds
19–24 Oct
4.95 out of 5 average rating, 39 reviews
Photo 1 of 19
Guest favourite
Home in Cudjoe Key
Relaxing and Inviting home with 35' Private Dock
2 bedrooms, 2 queen beds
1–6 Oct
4.85 out of 5 average rating, 61 reviews
Photo 1 of 7
Camper van/Motorhome in Cudjoe Key
Venture Out Ocean View Canal RV lot in Cudjoe Key
1 bed
1–6 Oct
New place to stay
Photo 1 of 17
Featured hotel
Hotel in Key West
Silver Palms Inn & Historic Homes, Classic Double.
1 bedroom, 2 queen beds
16–21 Oct
4.81 out of 5 average rating, 86 reviews
Photo 1 of 29
Superhost
Home in Cudjoe Key
Latitudes & Attitudes
3 bedrooms, 5 beds
16–23 Nov
Photo 1 of 26
Superhost
Home in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock
2 bedrooms, 4 beds
15–20 Oct
4.89 out of 5 average rating, 185 reviews
Photo 1 of 29
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds
1–6 Oct
New place to stay
Photo 1 of 21
Featured hotel
Hotel in Key West
Havana 2 queens
1 bedroom, 2 queen beds
1–6 Oct
Photo 1 of 6
Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed
1–6 Oct
4.9 out of 5 average rating, 621 reviews