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Upper Florida Keys Vacation Rentals(244)

244 Results
$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,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(10)
$996 - $1,133
per night
1 - 30 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 10
1 - 30 night minimum stay
(9)
$275 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(5)
$300
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(11)
$250 - $375
per night
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
1 Review
$250 - $350
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$275 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$275 - $375
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
$220 - $325
per night
3 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(5)
$275 - $450
per night
3 - 7 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$275 - $425
per night
3 - 4 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 4 night minimum stay
(5)
$185
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
3 night minimum stay
(5)
$275 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night minimum stay
$299 - $450
per night
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$150 - $200
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
$250 - $350
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
$299 - $450
per night
3 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night minimum stay
$300 - $450
per night
3 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
3 - 7 night minimum stay
$300 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night minimum stay
$299 - $450
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
$225 - $300
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 16
28 night minimum stay
(27)
 

Recent Upper Florida Keys Reviews

Fabulous and Unique. Great Rental!

5 of 5
Our family had an amazing time staying on the Calypso houseboat. The boat had everything we wanted in a rental, clean and spacious, the beds were super comfortable and the kids had their own rooms. The location (Pilot House Marina) was perfect. There was even a restaurant at the marina that I highly recommend and the bar (Glass Bottom Bar) is right over the water and has glass floors so you can see down into the water. My most favorite part of the houseboat experience was spending the evening on the roof deck watching the sun set. Several nights we made home cooked meals and just hung out up there as a family taking it all in. Soooooooo perfect! The kids loved it so much they can't wait to go back!
  • Submitted: Oct 26, 2014
  • Stayed: Aug 2014

Great getaway spot!

5 of 5
While I went there on a girls weekend, I could easily visualize bringing my whole family. The house was clean and well maintained as well as all the grounds and pool. We spent a lot of time lounging by the immaculate pool with a beautiful view of the water. The pool was super close to the house so if we needed a snack we just ran back. The house is within walking distance to restaurants, or a quick drive (especially this great breakfast joint) or has everything you need to dine in. With easy access to the main road I'd like to go back and explore more of the keys. The owners were super easy to work with, quick to respond and I would defiantly stay there again.
  • Submitted: Oct 8, 2014
  • Stayed: Jun 2014

Great value

4 of 5
The house was huge and had everything we needed for 9 people. Value was excellent and location central to Miami and Key West was also great. Management was very responsive and overall, great. I'd go back in a heartbeat.
  • Submitted: Aug 6, 2014
  • Stayed: Jul 2014