Updating...
Match: Rental types Private outdoor pool (heated)
All filters matchPrice per night from
$172
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$481
BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$382
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$478
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
Key West apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$840
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$458
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
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$2,119
Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,145
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park
Key West apartment
- 2 bedrooms
- 1 bathroom
- sleeps 4
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$573
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$974
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$478
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$764
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
Somewhere on the Beach a dream property all amenities included simply amazing
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,432
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,145
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,374
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$382
Ocean View Monthly Rental at 1800 Atlantic- Open Nov, December & January
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$172
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
Key West house
- 1 bedroom
- 1 bathroom
- sleeps 4
“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$796
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$974
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$382
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
Key West apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,718
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$745
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$802
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$344
Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!
Key West house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$165
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,374
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
Our Nautical Home in Key West is available for amazing prices Summer of 2023
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$974
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,374
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$745
High Tide awaits your next visit upgraded condo close to Smathers Beach
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Rental types, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$859
1 of 2 match: Private outdoor pool (heated), Rental types
1 of 2 filters matchPrice per night from
$172
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean
Key West condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Private outdoor pool (heated), Rental types
1 of 2 filters matchPrice per night from
$487
Responds fast! avg. 3 hours 48 minutes
1 of 2 match: Private outdoor pool (heated), Rental types
1 of 2 filters matchPrice per night from
$107