Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Florida Keys Downtown Vacation Rentals Vacation Rentals(248)

248 Results
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(28)
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(13)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(31)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
(23)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(47)
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
(12)
3 - 6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(17)
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(39)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(9)
3 - 4 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
(15)
4 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 14
(48)
7 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
(41)
7 night minimum stay
  • 7 BR,
  • 7 BA,
  • Sleeps 12
(30)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(24)
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
(21)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(21)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(28)
4 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 6
(58)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(39)
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
(8)
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(26)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(20)
4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(28)
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(12)
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(18)
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(16)
4 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
(26)
4 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 12
(16)
4 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(12)
4 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(11)
 

Recent Florida Keys Reviews

Wow! Best place and location in Key West!

5 of 5
We stayed in Truman Annex for the first time and found the former Navy site to be the best location in Key West. As a frequent visitor to Key West, we no longer will consider hotels, B&Bs and remote condos. Flip Flop Retreat is walking distance to everything we wanted in KW: Beaches, Duvall Street restaurants and entertainment, Mallory Square, historic sites, and water activities. If that wasn't enough- the parking spot was steps away, the pool was at the back gate, and the first floor powder room was convenient for guests. Flip Flop was clean as can be, thoughtfully decorated, and had all the entertainment we could need. We will return!
  • Submitted: Aug 24, 2014
  • Stayed: Aug 2014

Great place and a gret time!

5 of 5
We loved the location and this home. Everything went smoothly and I highly recommend this property. Thanks again for a great trip.
  • Submitted: Aug 24, 2014
  • Stayed: Jun 2014

Great vacation in the Keys

5 of 5
Could not have asked for a better place. Location was great, home was very nice and service was wonderful. Everything we needed was walking distance. The Green Parrot and Scooner Wharf were favorite places for a cold beers and music. 5 stars all the way around!
  • Submitted: Aug 24, 2014
  • Stayed: Jul 2014