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(61)

61 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
  • 2 BR,
  • 2 BA,
  • Sleeps 8
$8,250
per month
28 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 8
28 night minimum stay
(5)
  • 2 BR,
  • 1 BA,
  • Sleeps 12
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(4)
  • 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 10
$2,800 - $3,200
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(20)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 12
27 - 30 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 6
(10)
$1,975 - $2,875
per month
28 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 9
28 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(8)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
(17)
  • 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)
34 more choices from the HomeAway Network
$2,679
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(10)
$100 - $220
per night
2 - 6 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 6 night minimum stay
(5)
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(18)
Advertisement
 

Recent Big Pine Key Reviews

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

Excellent stay!

5 of 5
We stayed at the beautiful Casa Domingi a few weeks ago and thoroughly enjoyed our stay. We've been going to the Keys for lobster season for years so we've stayed in many different places, but this one was one of the best. The owners go to great lengths to make you feel at home. They left a binder full of great info about things to see & do, as well as how to operate electronics in the house. The fresh fruit in the fridge was awesome after a long, sweltering car ride. I could go on & on about all of the great things, but I'll hit the high points for the sake of time. There was an abundance of white, soft, fluffy towels. This may seems like a little thing, but I can assure you that towels run short when 8 people shower every night & scratchy towels are horrible on sunburned skin. Who wants to spend their vacation doing laundry? The individual air conditioners in the bedrooms were awesome!!! The kids loved the good wifi. Kitchen was stocked with everything we needed, but the can opener was hard to operate so we made a donation to the cutlery drawer lol! Loved the large, high end fridge/freezer. Of course the balcony area right off of the two bigger bedrooms was a favorite of all that stayed. The owners were staying less than 15 minutes so they provided their cell phone in case we had any trouble at all...which we didn't. The only negatives are things that the owners can not help but definitely warned us about. The noseeums were horrible & laughed at our bug sprays. Also, the water is very shallow in front of the sea wall. We did scratch the bottom of our new boat on the rocks a few times. Although it's only 22 feet, it is very heavy & we had a hard time going out & coming in even at an angle (we were very envious of the dock at the adjoining property). Once you get past the rocks, you are just a quick ride to the open water. Lastly, I got my deposit back in less than 2 weeks. I have had problems with 2 other properties in the past, as those owners obviously don't put it in trust as these owners do. That was a pleasant surprise, as I was expecting 4-6 weeks before seeing a check in the mailbox. Again, as an avid traveler to the Keys for lobstering, I put Casa Domingi at the top of the list of properties we have stayed at. Will definitely rent from these owners in the future!
  • Submitted: Aug 27, 2014
  • Stayed: Aug 2014