Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Florida Keys Vacation Rentals(914)

914 Results
$1,995 - $2,900
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
7 night minimum stay
(41)
$350 - $484
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(82)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(91)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(36)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(34)
$175 - $400
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
(27)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 night minimum stay
(33)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 29 night minimum stay
(57)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(23)
$1,300 - $1,950
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(28)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(65)
$135 - $160
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 night minimum stay
(38)
$1,300 - $2,400
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
(45)
$175 - $400
per night
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
4 - 5 night minimum stay
(15)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 13 night minimum stay
(17)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(32)
$2,150 - $3,550
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(21)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(36)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 - 5 night minimum stay
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(40)
$120 - $400
per night
3 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 4 night minimum stay
(32)
$185 - $270
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(24)
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(50)
$2,100 - $2,450
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(12)
$1,197 - $2,150
per week
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
3 - 7 night minimum stay
(28)
$450
per night
6 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
4 night minimum stay
(68)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(15)
 

Recent Florida Keys Reviews

Would Rent Again

5 of 5
We rented Billies Blue Haven and loved the room and Amenities it gave us. We were in Key West for a conference, a writing environment, and a Romantic week together. This place supplied all our needs. The Kitchen, the Washer & Dryer, the bikes, and the proximity were great. The only issue was the internet connection, and some pounding next door one night, but the rest was great! We enjoyed snorkeling, walking on the beach and ease of access to shopping. We would recommend this place to others spending time in Key West! Thank You!
  • Submitted: Sep 23, 2014
  • Stayed: Sep 2014

Excellent condition as expected; no surprises.

5 of 5
wife and I had great time------doing what we wanted, when we wanted, where we wanted! wife said "best vacation I've ever had"! good restaurants, great fishmonger. great having pool at our feet. wish primary t.v. was HD. no one to greet us and do a "walk-around" but we overcame that quickly! never met the neighbors which disappointed us, as we were told how helpful and friendly they were. i'm not prone to knock on doors and it would have been great had the owners contacted the neighbors and given them our names and cell phone numbers. wife did snorkel trip and paddle board trip and we did charter fish trip which was a tourist rip-off------I should have known better! we needed a private fish guide instead. would definitely recommend to anyone. had incredible meal at Frank's----osso bucco lamb-----anything on menu Is worthy.don't miss the huge Bass Pro Shop in Isla morada-----a destination, and a great restaurant they own on the dock next door--great sunset spot too!
  • Submitted: Sep 23, 2014
  • Stayed: Sep 2014

Just right - comfortable, affordable, fun

4 of 5
My husband and I stayed for 3 nights and we made the most of it. Used hot tub, cooked out on the grill provided, brought our own bikes which we could safely store on the deck and rode all over starting with the bike path across the street, walked to beach, mimosas on the deck, and rainy day cuddling on the couch. It was instantly welcoming and comfortable. We did not want for anything. The location was great...an easy bike ride to Duval Street/Mallory Square or the management provided a handy book with information on where to find parking (they were spot-on). It is a really short bike ride down a wide path to Martello Tower & White Street pier. There is a beach within walking distance, but Key West is not known for its great beaches. There was also fishing gear available for us to use, a very nice touch.
  • Submitted: Sep 20, 2014
  • Stayed: Sep 2014