Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Key West Vacation Rentals with Online Booking(265)

265 Results
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(40)
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(82)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(36)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(28)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(65)
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(45)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(31)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
(24)
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(30)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(40)
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(23)
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(23)
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(24)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(18)
1 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(17)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(17)
1 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(22)
1 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(16)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(17)
1 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(16)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(15)
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
(15)
1 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
(15)
1 - 7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
(17)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
(14)
1 - 7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
(15)
1 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(15)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(13)
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
(12)
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(13)
Advertisement
 

Recent Key West Reviews

Perfect family getaway

5 of 5
The place is beautifully decorated and homey. The terrace and view amazing. Could sit out there for days. Fit 6 of us very comfortably, all the amenities you need are there. Pool is very nice the only thing that would have added to it would have been cool water. It was like a bath. Will definitely return if at all possible. Even check on and check out was easy.
  • Submitted: Aug 30, 2014
  • Stayed: Aug 2014

Incredible vacation Rental!!!

5 of 5
We have stayed in MANY townhouses in Truman Annex, Flip-flop was by far the best experience yet!!! Beautiful, clean and well-stocked home that made the vacation so comfortable. Having the pool right behind the townhouse was such a plus...we would hit the beach for a couple hours and then jump into the pool before getting ready for dinner. Ward was awesome from the beginning of the process to the very end. Will definitely be returning!!!!
  • Submitted: Aug 30, 2014
  • Stayed: Jul 2014

Private getaway. Quiet and relaxing.

5 of 5
Accurate description and photos regarding location, amenities and size of house and property. Property and was clean and cool when we arrived. We would definitely stay here again and have recommended the cottage to family and friends. Already trying to figure out when we can return. Received good customer service, called with a question regarding the pool and someone was out that same day to check things out. Whenever we are in Key West we always eat at Commodores, one of our favorite places by the water. Enjoyed shopping and site seeing on Duval Street and also took a Sunset Dinner Cruise. We always have a good time in Key West and have stayed in hotels in the past. But after staying at Papa's Hideaway "Garden of Eden" this may be our new favorite place to stay.
  • Submitted: Aug 27, 2014
  • Stayed: Aug 2014