Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Big Pine Key Vacation Rentals(59)

59 Results
$3,800 - $4,000
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(38)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
4 - 7 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(17)
$2,400 - $3,400
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
7 night minimum stay
(25)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
30 night minimum stay
(5)
$7,800
per month
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
2 Reviews
$4,300 - $5,400
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 9
7 night minimum stay
(6)
$8,250
per month
28 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
$2,200 - $3,200
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(11)
$2,600 - $3,500
per month
28 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 4
28 night minimum stay
(12)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
28 night minimum stay
1 Review
$2,975
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(21)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
27 - 30 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 6
(10)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
(17)
$3,995 - $5,957
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
1 Review
$1,290
per week
7 - 28 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
7 - 28 night minimum stay
1 Review
$1,975 - $2,875
per month
28 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 9
28 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(11)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(28)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 9
(5)
31 more choices from the HomeAway Network
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(18)
$2,679
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(10)
Advertisement
 

Recent Big Pine Key Reviews

Excellent as always! This was our third year here!

5 of 5
Once again a great stay! We returned for the 3rd year in a row, great as always!September is a quiet time in the Florida Keys, gave us a chance to enjoy Big Pine Key, the outdoors and the all that this house has to offer. Already looking forward to our next visit!
  • Submitted: Oct 2, 2014
  • Stayed: Sep 2014

Great VAcation

5 of 5
My wife and me found a great place. It is perfect quiet an relaxable. Clean and friendly proberty. Close to Bar, Supermarket and everything. We found it only great. Marco
  • Submitted: Sep 15, 2014
  • Stayed: Aug 2014

Exceptional

5 of 5
My husband and I have been renting homes in the Key's for 25 plus years. Casa Jose' is by far the best home we have had the pleasure of staying in. The accommodations were first class. We love to cook and the kitchen had everything we could want. The home was fully equipped with all of our needs (linen's, paper products etc) The beds were very comfortable. The location and the cleanliness of the canal were also a big part of our satisfaction with this property. Some canal's are very narrow and stink...this one was clean and easy to navigate. The owner John was very accommodating and easy to work with. We will absolutely stay here from now on.
  • Submitted: Sep 6, 2014
  • Stayed: Aug 2014