332 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Florida Keys Downtown Vacation Rentals(332)

332 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
(57)
$1,300 - $1,950
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(32)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night minimum stay
(33)
  • 2 BR,
  • 3 BA,
  • Sleeps 6
3 - 6 night minimum stay
(72)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(33)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night minimum stay
(30)
$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,
  • 1 HF BA,
  • Sleeps 6
6 night minimum stay
(22)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 3 night minimum stay
(34)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night minimum stay
(28)
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 7 night minimum stay
(18)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(13)
$1,600 - $3,500
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(5)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
6 night minimum stay
(27)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(24)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 6 night minimum stay
(15)
$3,600 - $7,800
per month
28 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
28 - 30 night minimum stay
(13)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 6 night minimum stay
(13)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 6 night minimum stay
(36)
$365 - $550
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 5 night minimum stay
(25)
  • 7 BR,
  • 7 BA,
  • Sleeps 16
4 - 6 night minimum stay
(22)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 6 night minimum stay
(28)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
27 night minimum stay
(7)
  • 5 BR,
  • 4 BA,
  • Sleeps 14
3 - 6 night minimum stay
(63)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
28 night minimum stay
(17)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(49)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
27 night minimum stay
(12)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
27 night minimum stay
(14)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
6 night minimum stay
(9)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
28 night minimum stay
(10)
 

Recent Florida Keys 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

Beautiful home for the holidays

5 of 5
It was truly magical, spending the Christmas and New Year holidays in this wonderful home! We enjoyed the large pool area daily for swimming and we were able to enjoy many of our meals outside, which was lovely. We had bikes to get us all around the island to the nearby beaches. This home was so bright and cheerful! Lori was always available for any questions we had and for anything we needed. It was definitely a 5 star vacation for our family and friends.
  • Submitted: Mar 21, 2015
  • Stayed: Dec 2014

Awesome!

5 of 5
Beautifully furnished property, well equipped for vacationers, excellent Key West location. The reservation procedure, through Last Key, was uncomplicated. We were greeted by Shel, who made sure the accommodations were in order, and they were! He was readily available during the week also, for a minor malfunction. We enjoyed dinners at Bagatelle, Ambrosia, Two Cents, Half Shell Raw Bar, AB Lobster House, and Sarabeth's. And of course, Flamingo Crossing IceCream! We will definitely be back!
  • Submitted: Mar 20, 2015
  • Stayed: Feb 2015