Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Condos
Cottages
Homes
Studios
Yachts
Barns
Bungalows
Cabins
Castles
Chalets
Estates
Farmhouses
Hotels
Lodges
Townhomes
Villas

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Key West Ski Vacation Rentals(33)

33 Results
$250 - $500
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 5 night minimum stay
(42)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(6)
$5,950 - $8,500
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
28 night minimum stay
2 Reviews
$7,500 - $9,600
per month
28 night minimum stay
  • Studio,
  • Sleeps 6
28 night minimum stay
(5)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night minimum stay
(3)
$275
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 8
7 night minimum stay
$219 - $249
per night
3 - 4 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
3 - 4 night minimum stay
$365 - $480
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
$1,300 - $1,850
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
(24)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
(32)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$190 - $330
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(16)
$95 - $200
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night minimum stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 Reviews
  • 1 BR,
  • 1 BA,
  • Sleeps 2
28 night minimum stay
$8,000 - $9,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 night minimum stay
1 Review
$23,000 - $29,000
per month
30 night minimum stay
  • Studio,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 22
30 night minimum stay
13 more choices from the HomeAway Network
  • 3 BR,
  • 4 BA,
  • Sleeps 7
28 night minimum stay
(4)
$300 - $400
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 night minimum stay
(5)
$8,500 - $12,000
per month
30 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 10
30 night minimum stay
(16)
$179 - $395
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
1 Review
$179 - $300
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
$179 - $395
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
$179 - $395
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
1 Review
$250 - $300
per night
5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
5 night minimum stay
(4)
$200 - $350
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(7)
$175 - $349
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
2 Reviews
Advertisement
 

Recent Key West Reviews

BEST CONDO, BEST LOCATION, BEST OWNER IN KEY WEST!

5 of 5
WE JUST RETURNED FROM KEY WEST ON NOV.11, 2014 AND WE WISH WE COULD HAVE STAYED IN JEAN'S "ISLAND ESCAPE" FOREVER!!! WE HAD STAYED PREVIOUSLY IN KEY WEST ON SMATHER'S BEACH, AND EVEN THOUGH IT IS A VERY NICE BEACH, THAT EXPERIENCE DID NOT COME CLOSE TO THE TIME WE HAD IN JEAN'S "ISLAND ESCAPE" IN THE TRUMAN ANNEX. WE JUST DROVE THE SHORT DRIVE TO SMATHER'S BEACH WHEN WE WANTED TO SPEND TIME THERE, WHICH WAS ONLY ONE TIME IN THE WEEK WE WERE IN KEY WEST, BECAUSE WE DIDN'T WANT TO TAKE TIME AWAY FROM THE BEAUTIFUL "ISLAND ESCAPE" AND ALL IT HAS TO OFFER. THE CONDO ITSELF IS ABSOLUTELY BEAUTIFUL. IT OFFERS EVERYTHING YOU COULD POSSIBLY NEED IN A "HOME AWAY FROM HOME". IT WAS THE MOST COMFORTABLE CONDO WE HAVE EVER STAYED IN ANYWHERE, AND WE HAVE STAYED IN A LOT OF DIFFERENT CONDOS ON VACATIONS. THE COVERED PORCH IS TO DIE FOR. IT IS HUGE!!! YOU COULD JUST LIVE OUT THERE, AND VERY COMFORTABLY, BECAUSE OF THE PRIVACY AND THE TWO CEILING FANS ON IT. WE SPENT A LOT OF TIME OUT THERE AND JUST LOVED THE PEACE AND QUIET IT OFFERED. THE GROUNDS OF TRUMAN ANNEX ARE BEAUTIFUL AND VERY, VERY WELL KEPT, AS IS THE POOL AREA. WE SPENT A LOT OF TIME AT THE POOL AND MET SOME OF THE NICEST PEOPLE, SOME OWNERS AND OTHERS JUST VACATIONERS LIKE OURSELVES. WE ENJOYED THE CONVERSATIONS WITH ALL OF THEM. WE REALLY ENJOYED BEING WITHIN WALKING DISTANCE OF EVERY- THING WE REALLY WANTED TO DO IN KEY WEST. WHEN WE STAYED ON SMATHER'S BEACH BEFORE, WE HAD TO DRIVE EVERYWHERE WE WENT. THAT WAS VERY MUCH AN INCONVENIENCE, AND PARKING WAS A NIGHTMARE. EVEN WHEN WE FINALLY FOUND A PARKING SPACE, WE HAD TO MAKE SURE WE PUT IN ENOUGH MONEY FOR THE AMOUNT OF TIME WE WOULD BE GONE. IF WE DIDN'T, WE WOULD HAVE TO RUN ALL THE WAY BACK TO THE CAR TO PUT MORE MONEY IN OR RISK GETTING A TICKET. STAYING IN JEAN'S "ISLAND ESCAPE", WE COULD WALK EVERYWHERE WE WANTED AND BE GONE AS LONG AS WE WANTED WITHOUT ANY WORRIES. IT WAS WONDERFUL!!! ALSO, WE FELT VERY SAFE COMING BACK TO THE PROPERTY VERY LATE AT NIGHT BECAUSE THERE WAS VERY GOOD SECURITY SURROUNDING THE PROPERTY. AND LASTLY, BUT FAR FROM LEAST, IS JEAN, THE OWNER. SHE IS JUST WONDERFUL TO DEAL WITH. SHE NEVER FAILED TO ANSWER ANY QUESTIONS I HAD AND RETURNED MY E-MAILS SO QUICKLY. WE WILL NEVER STAY ANYWHERE IN KEY WEST BUT JEAN'S "ISLAND ESCAPE". THANK YOU, JEAN, FOR EVERYTHING!!!
  • Submitted: Nov 16, 2014
  • Stayed: Nov 2014

Lovely place to stay with great pool!

4 of 5
Great location. Lovely, open and inviting house with eclectic artwork and wonderful pool.
  • Submitted: Nov 2, 2014
  • Stayed: Apr 2014

Amazing

5 of 5
This is such an amazing property. The sunrises off the balcony are absolutely beautiful. It has everything you need and not very far from where you need to go. This is a great place to get away from it all and just unwind
  • Submitted: Oct 18, 2014
  • Stayed: Sep 2014