Updating...
Islamorada Ocean Views! Pool, Wi-Fi, Balcony, Gym, Covered Parking
Islamorada condo
- 2 bedrooms
- 2 bathrooms
- sleeps 4
Responds fast! avg. 2 hours 44 minutes
Match: Games room Private outdoor pool (heated)
All filters matchPrice per night from
$172
Sunchasers Paradise - spacious lux canal front home, private pool/spa, 80' dock
Marathon house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
Match: Games room Private outdoor pool (heated)
All filters matchPrice per night from
$819
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$359
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$434
Private House Facing the Ocean with Heated Pool/Spa
Ramrod Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$410
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,148
Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!
Key Colony Beach house
- 2 bedrooms
- 1 bathroom
- sleeps 4
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$343
Yellow vacation home, water view, boat dock, heated private pool.
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$476
Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL
Grassy Key house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$567
Blue Palms Retreat. ocean front w/pool and dock for your boat.
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$573
5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks
Little Torch Key house
- 3 bedrooms
- 3 bathrooms
- sleeps 7
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$307
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$481
Blue vacation home, water front, boat dock, heated private Pool.
Summerland Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$556
Come relax in Islamorada, the tropical jewel of the Florida Keys!!
Islamorada apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$201
Beautiful quiet neighborhood. Sunsets! Huge Pool!
Sugarloaf Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 30 minutes
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$320
Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn
Islamorada house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$784
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$285
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$286
New Upscale, private pool, Dockage, kayaks, bikes, downtown Islamorada locale
Islamorada house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$911
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$975
“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$801
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$659
Stunning Waterfront 4 Bedroom 4 Bath, Heated Pool w/dockage,2 Kayaks, Fishlights
Marathon house
- 4 bedrooms
- 4 bathrooms
- sleeps 10
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,317
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$802
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$478
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$458
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
Key West apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$840
BOOK MARGARITAS IN PARADISE KEY WEST LUXURY MONTHLY CONDO BEST VALUE
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$382
Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards
Summerland Key house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$1,718
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$134
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
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$402
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$413
“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!
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$573
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$790
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$621
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
Islamorada house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
“Comfortable home for family get-together” Positive experience overall: Our family of six adults had a tropical-feeling destination Christmas here. The house easily accommodated all of us, and we enjoyed the wrap-around porch and pool. We appreciated the commodious kitchen with a two-tier dishwasher and side-by-side refrigerator with ice/water dispenser. Having a washer and dryer on the premises was very helpful, since guests are requested to wash linens and towels before departing. Some drawbacks: the house did not come equipped with adequate staples, such as paper products, laundry detergent, and garbage bags, so be prepared to purchase these. There are no beaches or stores within walking distance. On a couple of nights, noisy neighbors talking on the street woke us up. (In general, though, the area is quiet.)
Responds fast! avg. 1 hour 0 minutes
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$670
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: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$2,119
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
1 of 2 match: Games room, Private outdoor pool (heated)
1 of 2 filters matchPrice per night from
$382