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Blue vacation home, water front, boat dock, heated private Pool.
Summerland Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
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$558
Match: Private pool
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$380
Match: Private pool
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$518
Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards
Summerland Key house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
Match: Private pool
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$1,725
Luxury Oceanview Pool Eco-friendly Villa Near Key West
Summerland Key villa
- 4 bedrooms
- 2 bathrooms
- sleeps 12
Match: Private pool
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$701
Match: Private pool
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$288
Match: Private pool
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$287
Great rentals within 20 miles that match your search
Match: Private pool
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$794
Price per night from
$624
Yellow vacation home, water view, boat dock, heated private pool.
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$478
Blue Palms Retreat. ocean front w/pool and dock for your boat.
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
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$575
5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks
Little Torch Key house
- 3 bedrooms
- 3 bathrooms
- sleeps 7
Match: Private pool
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$309
Match: Private pool
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$253
$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
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$259
Beautiful quiet neighborhood. Sunsets! Huge Pool!
Sugarloaf Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 30 minutes
Match: Private pool
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$321
Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK
Stock Island house
- 4 bedrooms
- 3 bathrooms
- sleeps 11
Match: Private pool
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$803
Match: Private pool
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$360
Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access
Little Torch Key house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Responds fast! avg. 24 minutes
Match: Private pool
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$403
“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!
Match: Private pool
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$575
Match: Private pool
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$435
Private House Facing the Ocean with Heated Pool/Spa
Ramrod Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Match: Private pool
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$411
Waterfront Beach House with Dock and Heated Pool!
Little Torch Key house
- 8 bedrooms
- 5 bathrooms
- sleeps 20
Match: Private pool
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$804
Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.
Cudjoe Key house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Match: Private pool
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$518
Ocean View Estate with Private Pool 15 minutes from Key West
Cudjoe Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 10
“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.
Responds fast! avg. 2 hours 26 minutes
Match: Private pool
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$604