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Search results; Over 1,000 places in Summerland Key

Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
3 beds
May 12 – 17
4.68 out of 5 average rating, 28 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 beds
Apr 29 – May 4
4.45 out of 5 average rating, 11 reviews
Home in Summerland Key
Beach House Key West, with a daily rentals license
9 beds
Apr 22 – 27
4.59 out of 5 average rating, 27 reviews
Guest favorite
Home in Ramrod Key
Canalfront 3BD/2BA|FLKeys|POOL|DOCK
6 beds
Mar 6 – 11
5.0 out of 5 average rating, 6 reviews
Guest favorite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
WaterfrontSea and bay views,
Aug 17 – 22
4.97 out of 5 average rating, 61 reviews
Guest favorite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
4 beds
Oct 1 – 8
4.94 out of 5 average rating, 17 reviews
Superhost
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
6 beds
May 2 – 7
4.88 out of 5 average rating, 16 reviews
Home in Summerland Key
Peaceful Paradise- Summerland Cove!
3 beds
Mar 15 – 20
New place to stay
Home in Summerland Key
Pelico Palms Sunset Cottage
4 beds
Apr 20 – 25
4.91 out of 5 average rating, 23 reviews
Home in Big Pine Key
Nature's Paradise-Ingrd Pool-Great Monthly Rental$
4 beds
May 15 – 22
Home in Summerland Key
Powell Family Resort
7 beds
Apr 22 – 27
4.86 out of 5 average rating, 35 reviews
Home in Key West
Waterfront Key West House w/Dock
6 beds
May 8 – 14
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Big Pine Key
Home in Big Pine Key
2 beds
Apr 23 – 28
5.0 out of 5 average rating, 12 reviews
Home in Summerland Key
2 Bedroom Sunset Bungalow
2 king beds
Apr 20 – 25
4.7 out of 5 average rating, 90 reviews
Home in Cudjoe Key
Canal 3bedroom 2 bath home
Mar 12 – 17
New place to stay
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
Apr 28 – May 3
4.86 out of 5 average rating, 42 reviews
Guest favorite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
4 beds
May 26 – 31
4.91 out of 5 average rating, 145 reviews
Guest favorite
Home in Cudjoe Key
Paradise in Cudjoe! Perfect Family Home!
4 beds
Oct 4 – 9
5.0 out of 5 average rating, 22 reviews