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Search results; Over 1,000 homes in Summerland Key

Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds
12–17 Aug
4.8 out of 5 average rating, 80 reviews
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
9–14 Aug
4.93 out of 5 average rating, 73 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 204 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds
3–8 Aug
4.97 out of 5 average rating, 32 reviews
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 bed
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed
2–7 Aug
4.89 out of 5 average rating, 618 reviews
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 43 reviews
Guest favourite
Home in Summerland Key
Private Pool Oasis | 3 King Suites | 30 Min to KW
3 bedrooms, 4 beds
1–6 Aug
4.84 out of 5 average rating, 62 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Cudjoe Key
101- Oceanside House with Pool
2 bedrooms, 2 king beds
1–6 Aug
4.89 out of 5 average rating, 258 reviews
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
1–6 Aug
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds
13–18 Sept
4.97 out of 5 average rating, 88 reviews
Guest favourite
Flat in Key West
Key West Beach House
2 bedrooms, 2 beds
1–8 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Home in Cudjoe Key
Waterfront 2BR w/ Dock & Pool Access
2 bedrooms, 3 beds
1–6 Aug
4.86 out of 5 average rating, 29 reviews
Guest favourite
Home in Cudjoe Key
Paradise Palms in Cudjoe Key #635
2 bedrooms, 3 beds
2–7 Aug
4.96 out of 5 average rating, 25 reviews