Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Upper Florida Keys Vacation Home Rentals with Air Conditioning(408)

408 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(23)
$450
per night
6 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(15)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(33)
$1,495 - $1,895
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(14)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
(29)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(26)
  • 2 BR,
  • 2 BA,
  • Sleeps 9
3 - 5 night minimum stay
(6)
  • 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
2 Reviews
$349 - $449
per night
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
3 night minimum stay
2 Reviews
$4,172 - $5,600
per month
28 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 10
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(27)
$699 - $943
per night
5 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • 2 HF BA,
  • Sleeps 12
5 - 7 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 5
7 night minimum stay
(19)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(12)
$30,000 - $37,500
per month
28 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 10
28 night minimum stay
(8)
$6,000 - $9,000
per month
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
7 night minimum stay
(16)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
1 Review
$1,700 - $2,400
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night minimum stay
(24)
$4,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(9)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
2 Reviews
$2,300
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
7 night minimum stay
(12)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
2 Reviews
  • 5 BR,
  • 3 BA,
  • Sleeps 16
28 night minimum stay
(27)
 

Recent Upper Florida Keys Reviews

Lovely holiday home

5 of 5
My wife and myself spent a lovely week here that went far too fast. Mike and Maria were waiting for us when we arrived and made sure we knew how everything worked before they left. The photos of this house do not do it justice. The house was spotless and the kitchen very well stocked. In fact we did not eat out once here as we wanted to spend as much time enjoying the beautiful view as possible. The underwater lighting was magical and we saw lots of different fish, crabs, dolphins, small sharks and even manatees from a distance. The kayak was great fun also. We hope to return one day and would definitely recommend this holiday home.
  • Submitted: Oct 18, 2014
  • Stayed: Sep 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

The layout of the area was very enjoyable.

4 of 5
The overall layout of the property was pretty cool, having young kids the safety factor at this location is really good. The boat slips are easy and the swimming pool is great. The house itself was clean and enjoyable. See no reason we will not want to stay here on our next trip to the keys. Keith Morgan
  • Submitted: Sep 16, 2014
  • Stayed: Jul 2014