163 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Key West Long Term Vacation Rentals(163)

163 Results
  • 3 BR,
  • 2 BA,
  • Sleeps 7
5 night minimum stay
(37)
$1,750 - $2,751
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(27)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 3 night minimum stay
(33)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(13)
$200 - $425
per night
7 - 8 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
7 - 8 night minimum stay
(11)
$210 - $395
per night
1 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 4 night minimum stay
(12)
$3,800 - $5,200
per month
27 - 28 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
27 - 28 night minimum stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
(56)
$1,400 - $2,700
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
(50)
$1,300 - $1,950
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(32)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(33)
$250 - $400
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
(14)
  • 3 BR,
  • 3 BA,
  • Sleeps 7
3 - 6 night minimum stay
(20)
$1,600 - $3,500
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 6 night minimum stay
(28)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(68)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
27 night minimum stay
(12)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
28 night minimum stay
(9)
$250 - $400
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
(6)
$298 - $600
per night
3 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 6 night minimum stay
(22)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
27 night minimum stay
(6)
$2,800 - $3,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(8)
  • 4 BR,
  • 5 BA,
  • Sleeps 10
28 night minimum stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
27 night minimum stay
(5)
$250 - $400
per night
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
27 night minimum stay
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(29)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
27 night minimum stay
2 Reviews
$2,900 - $8,500
per month
28 - 31 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
28 - 31 night minimum stay
2 Reviews
Advertisement
 

Recent Key West Reviews

A WEEK IN PARADISE

5 of 5
My wife and I and another couple visited Key West for the first time in March. We hit the jackpot by staying at Flip Flop Retreat. It was everything we expected and more. The location was key for all the activities we had planned to do. Ward was very courteous and helpful from day one. This will definitely be our home away from home next time we travel to the Keys. I highly recommend this condo for a great relaxing vacation.
  • Submitted: Mar 25, 2015
  • Stayed: Mar 2015

Score!

5 of 5
And, that we did! We visited Key West several times in the past and have stayed at many beautiful and luxury places. Needless to say this 5 star vacation home was the ultimate best place we stayed at, not only case in Key West, but in any home we have rented. The entities are endless! Hot tub, pool and spacious back yard is perfect for our kids and darling grand children. The privacy is priceless and keeps us moms and grandmoms feely secure! The house is absolutely stunning and has every thing you need to entertain guests or just relax as a couple. The kitchen and common areas are all equipped to live your everyday life of living in paradise for a month and feel like you can live like you're at your own home. With four bedrooms each equipped with a bathroom, will keep each guest happy and secluded with their own space! The location is priceless! Think of walking everywhere, to the fast lane of key west or walking to a secluded restaurant down the street, to enjoy a night out. If exercising is on the agenda there are several paths to run/walk/ and bike with rentals available a walk away. We haven't even been here the whole month and I can guarantee you, we are coming back. Kudos to the owners and the management staff, we are truly happy campers!
  • Submitted: Mar 16, 2015
  • Stayed: Mar 2015

octopus garden feb 2015

5 of 5
We arrived to a beautifully decorated exceptionally clean sweet smelling vacation home on Feb 1st 2015. When they said well stocked kitchen they mean it! Spices and various items such as extra tea bags, garbage bags,cleaning supplies , dish washer and laundry detergent were in ample supply on site. Plenty of towels and linens available for all three bed/bath suites. If yo don't favor the pillow on your bed just check the master closet. There are multiple pillows to choose your comfort from there. Lori Bailey was very responsive to all my requests and inquiries. The pool on site is perfect. We enjoyed the roosters and other fauna of stock island too. Close to the golf course and you'll get a discount because you're staying in the Coral Hammock complex. Places to eat near by are delicious. We Cycle will deliver bikes and you can easily bike all over key west . This was the best long term rental I have ever enjoyed. Thank you Lori! !
  • Submitted: Mar 5, 2015
  • Stayed: Feb 2015