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Upper Florida Keys(242)

242 Results
$175 - $400
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
(27)
$1,470 - $2,100
per week
7 night minimum stay
  • 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
(12)

Why HomeAway?

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No booking fees and low online prices
$24,500 - $37,500
per month
28 - 30 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 10
28 - 30 night minimum stay
(9)
$1,050 - $1,225
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
$2,350 - $3,200
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
3 night minimum stay
(5)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(3)
$220 - $300
per night
3 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(4)
  • 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
$275 - $400
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
(4)
$275 - $450
per night
3 - 7 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$150
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(3)
$425 - $550
per night
4 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 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
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
$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
  • 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
 

Recent Upper Florida Keys Reviews

A Perfect Islamorada Holiday Rental

5 of 5
This is a perfect Keys holiday rental. Islamorada is well located only 1.5hours from Miami Airport. The gated complex is safe, clean and friendly. The house is beautifully decorated, clean, well kept with everything you would expect and more. The pool area was quiet with a great view across the water. Susie was easy to deal with - quick communication and great advice. Highly recommend. We will be renting this house again.
  • Submitted: Jan 11, 2015
  • Stayed: Jan 2015

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

Wonderful Stay

5 of 5
Our stay at Ocean Reef was even more than we expected. The facility was a 5 star plus. Everything was clean and the staff really made you like you belonged. Linda's condo was clean and just the right size for our family of 4. Prior to our arrival Linda provided us with all of the information and tips we needed to make the post of our week. We can't wait to go back.
  • Submitted: Apr 15, 2014
  • Stayed: Apr 2014