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Upper Florida Keys Vacation Home Rentals(160)

160 Results
$1,495 - $1,895
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(14)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(23)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(20)
$4,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(7)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
$996 - $1,133
per night
1 - 30 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 10
1 - 30 night minimum stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 9
3 - 5 night minimum stay
(7)
$349 - $449
per night
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
2 Reviews
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(12)
$1,100 - $1,800
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(12)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
2 Reviews
$450
per night
6 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 night minimum stay
(16)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 15
3 - 5 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(33)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(29)
$750 - $943
per night
5 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • 2 HF BA,
  • Sleeps 12
5 - 7 night minimum stay
(4)
$300
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(10)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(25)
$4,172 - $5,600
per month
28 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 10
28 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
1 Review
  • 3 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
(10)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 night minimum stay
2 Reviews
$225
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
$6,000 - $9,000
per month
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
 

Recent Upper Florida Keys Reviews

Girl's Trip 2014!

5 of 5
"Amazing!" That is what we all kept saying during our stay at Largomar ! The house was so comfortable and spacious and fully stocked. We did not leave the house often because we couldn't pull ourselves away from the pool and hot tub area that over looked the gorgeous sea. We enjoyed the piped in music and awesome coffee/expresso maker in the kitchen. It is truly a beautiful place to get away , relax and enjoy the beauty of the Keys. Gorgeous sunrise views and perfect setting for sunset cocktails. It was a magical place!!
  • Submitted: Nov 19, 2014
  • Stayed: Nov 2014

Wonderful Oasis!

5 of 5
We rented this house with another couple to have a chill relaxed weekend in the keys. By the end of the first day we wanted to stay for a month! The place is beautifully decorated and comfortable. The place sits on a canal and has views of the water (canal and open water) all the way around the house. You can walk to the open water and a boat ramp or just stay in the house and enjoy the cool breezes and quiet neighborhood. Yes, there are trailers and houses surrounding the house but that's Florida! It was still lovely and peaceful. We will definitely go back again! Next time for at least a week!
  • Submitted: Nov 7, 2014
  • Stayed: Oct 2014

"Par Excellence"

5 of 5
"Par Excellence" This was a vacation of a lifetime for me. The house was absolutely perfect; it truly was home away from home! The location of the Angler's Reef complex is ideal for a great week in the Florida Keys. It is gated community, with beautiful landscaping. It has a “spa like” pool area with very clean bathrooms, as well as beach area that include chairs. Chris's unit is spacious and had all the basics for a great vacation. I particularly appreciated having all the extra amenities: WIFI, Comcast Cable, DVD player, Weber Grill, beach towels, and fishing rods. Nearby, there are nice restaurants and happy hour locations (w/the best drink specials)… and you don't need to spend a lot to have and a good time. My favorites were and Hog Heaven, Wahoo, Robbie’s (You can feed Tarpon), Ocean View, and Lorelei. Chris is an outstanding host and went out of his way to respond to questions and make my stay comfortable and fun. The highlight of my trip was swimming with the dolphins at Dolphin’s Cove. I picked this place over Theater of the Sea’s because I wanted my experience to be based on water interaction with the dolphins. It was absolutely amazing, I was in the water, by myself, with 5 dolphins, and I had a personal photographer that took 250 pictures. Let’s just say I will never forget my trip in Islamorada, and that’s all thanks to Chris!!
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014