Search results; Over 1,000 homes in Summerland Key

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Guest favorite
Home in Summerland Key
Sailfish Dream on Cudjoe Key-28 day minimum
6 guests2 bedrooms3 beds2 baths
Aug 17 – 22
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Aug 17 – 22
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ﺩ.ﺇ4,521 for 5 nights

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Guest favorite
Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
3 beds
Aug 24 – 29
ﺩ.ﺇ5,296 for 5 nights
4.84 out of 5 average rating, 62 reviews
Home in Summerland Key
Ocean front classic keys cottage
4 beds
Aug 2 – 9
ﺩ.ﺇ10,332 for 7 nights
Hotel in Key West
Coastal Comfort | Sunset-watching. Outdoor Pool
Free cancellation
Aug 26 – 31
ﺩ.ﺇ2,694 for 5 nights
New place to stay
Home in Summerland Key
A month in paradise pool home.
Free cancellation
Sep 7 – 12
ﺩ.ﺇ8,503 for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Marathon
Sunset Key Escape
Free cancellation
Sep 13 – 20
ﺩ.ﺇ11,507 for 7 nights
5.0 out of 5 average rating, 3 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
2 beds
Aug 6 – 11
ﺩ.ﺇ4,523 for 5 nights
4.9 out of 5 average rating, 339 reviews
Guest favorite
Home in Cudjoe Key
106 Newly Renovated House with Oceanview and Pool
2 king beds
Aug 9 – 14
ﺩ.ﺇ6,114 for 5 nights
4.93 out of 5 average rating, 180 reviews
Boat in Key West
Sailboat Stay: Explore & Relax
Free cancellation
Aug 9 – 14
ﺩ.ﺇ4,951 for 5 nights
New place to stay
Superhost
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5 beds
Aug 23 – 28
ﺩ.ﺇ17,375 for 5 nights
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
Free cancellation
Aug 31 – Sep 5
ﺩ.ﺇ10,993 for 5 nights
4.92 out of 5 average rating, 98 reviews
Home in Marathon
Canal Waterfront on Duck Key w/ Boat Dock & Pool!
4 beds
Aug 18 – 23
ﺩ.ﺇ6,791 for 5 nights
4.9 out of 5 average rating, 62 reviews
Home in Cudjoe Key
Beautiful Home w/Dock - Amenities-Gated Community
3 beds
Aug 1 – 6
ﺩ.ﺇ9,730 for 5 nights
New place to stay
Home in Cudjoe Key
Lochloosa in Cudjoe Key #655-summer openings!
Free cancellation
Aug 4 – 9
ﺩ.ﺇ5,705 for 5 nights
Guest favorite
Tiny home in Summerland Key
Lakefront Bungalow
1 bed
Aug 2 – 7
ﺩ.ﺇ5,024 for 5 nights
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Cudjoe Key
Oceanside home 111, dock,kayaks,bikes,pool,fishing
3 beds
Aug 3 – 8
ﺩ.ﺇ12,567 for 5 nights
5.0 out of 5 average rating, 17 reviews
Home in Cudjoe Key
Waterfront Venture Out Home
1 queen bed
Aug 11 – 16
ﺩ.ﺇ5,829 for 5 nights
4.84 out of 5 average rating, 68 reviews
Guest favorite
Home in Cudjoe Key
Yellow Home - Receive $500 towards a Boat Rental!
3 beds
Aug 2 – 9
ﺩ.ﺇ12,037 for 7 nights
4.84 out of 5 average rating, 32 reviews
Superhost
Boat in Marathon
Paradise awaits on this cozy houseboat!
Free cancellation
Aug 23 – 28
ﺩ.ﺇ4,038 for 5 nights
4.8 out of 5 average rating, 276 reviews