Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Upper Florida Keys Pet Friendly Vacation Rentals(293)

293 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(91)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(15)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(9)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 13 night minimum stay
(17)
$4,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(7)
$25,500 - $37,500
per month
28 - 30 night minimum stay
  • 4 BR,
  • 5 BA,
  • Sleeps 10
28 - 30 night minimum stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 9
3 - 5 night minimum stay
(7)
$1,800
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
7 night minimum stay
(3)
$12,000 - $13,200
per week
7 night minimum stay
  • 10 BR,
  • 8 BA,
  • 2 HF BA,
  • Sleeps 28
7 night minimum stay
(9)
$6,500 - $7,000
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(11)
$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)
$1,295 - $1,495
per week
7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night minimum stay
1 Review
  • 4 BR,
  • 4 BA,
  • Sleeps 12
7 night minimum stay
(16)
$220 - $325
per night
3 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night minimum stay
(4)
$1,295 - $1,495
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(18)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
1 Review
  • 3 BR,
  • 4 BA,
  • Sleeps 8
7 night minimum stay
(10)
$3,750 - $4,500
per week
5 - 7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 7 night minimum stay
(3)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 night minimum stay
2 Reviews
$185
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(5)
$150
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(3)
$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
  • 4 BR,
  • 2 BA,
  • Sleeps 14
28 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
5 night minimum stay
1 Review
 

Recent Upper Florida Keys Reviews

Great place, great time!

5 of 5
This was a wonderful trip! We stayed here last year with our dog and loved the location! The owner answered all my questions prior to my visit. It's off the beaten path and nice and private. We returned to find the same! There is road construction ongoing on the main road and you don't hear anything back here. The condo has everything you need. Very clean and stocked well in the kitchen. We fished from the dock and saw many varieties of fish. Lots of fun. We will hopefully be able to return next year!
  • Submitted: Nov 20, 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

Hammer Point Gem

5 of 5
This is our fourth rental in Hammer Point and we really enjoyed this house. House was very clean & well appointed. Everything was as described. The back yard was great and the canal was great for an afternoon dip. The Kitchen/great room was wonderful for the family to cook our catch & hang out with family & friends. Would have liked a TV in the master bedroom to catch up on the evening news, but other than that it was "perfect" nice neighbors also
  • Submitted: Aug 4, 2014
  • Stayed: Jul 2014