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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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$320
Great rentals within 20 miles that match your search
“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!
Match: Private pool
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$1,303
Price per night from
$622
BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking
Key West house
- 5 bedrooms
- 6 bathrooms
- sleeps 12
“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today
Match: Private pool
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$2,123
Price per night from
$345
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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$574
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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$308
Match: Private pool
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$482
Match: Private pool
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$172
Match: Private pool
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$379
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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$476
$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
Match: Private pool
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$253
Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West
Key West condo
- 3 bedrooms
- 4 bathrooms
- sleeps 8
Match: Private pool
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$316
Match: Private pool
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$286
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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$801
Price per night from
$689
Match: Private pool
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$434
Match: Private pool
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$359
Match: Private pool
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$287
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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$410
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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$402
Match: Private pool
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$975
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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$517
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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$700
Match: Private pool
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$792
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Key West villa
- 6 bedrooms
- 7 bathrooms
- sleeps 16
Match: Private pool
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$2,008
Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!
Key West house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$165
“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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$573
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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$544
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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$1,717
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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$800
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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$555
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$134
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$458
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$859
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Match: Private pool
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$859
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Match: Private pool
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$478