Big Pine Key Florida Vacation Rentals


Big Pine Key Vacation Rentals, Condos and Short Term Rental Accommodations

Book our vacation rentals with selection of 1,2,3 or 4 bedroom homes in Big Pine Key Florida. Search hundreds of properties, find the best deal when you book directly online.

Mango House 0
Vacation Home Rentals - Big Pine Key
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,000.00/Mo
Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall. This home offers 2 queen-size beds and an additional sle<... read more »
Island Time 2 0
Duplex Rentals - Big Pine Key
3 Bedroom(s) 1.0 Bath  Sleeps: 6
Starting at: $2,800.00/Mo
Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for pr... read more »
Manatee Bay 0
Vacation Home Rentals - Big Pine Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $2,900.00/Mo
Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic to fish and dive all... read more »
Breeze Swept 0
Vacation Home Rentals - Big Pine Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6
Starting at: $5,800.00/Mo
Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts décor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen T... read more »
Blue Heron 0
Vacation Home Rentals - Big Pine Key
2 Bedroom(s) 2.0 Bath  Sleeps: 4
Starting at: $2,575.00/Mo
Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all that great, fresh fish you're gonna catch. Easy... read more »
Our Island Thing 0
Vacation Home Rentals - Big Pine Key
3 Bedroom(s) 2.0 Bath  Sleeps: 6-8
Starting at: $5,200.00/Mo
A get away to “Our Island Thing” will be unforgettable vacation for everyone. Huge 1900 sq ft house with lots of room for the whole family and kids. 2 level concrete home is roomy and airy upstairs with huge kitchen, living and dining area, master be... read more »
Island Time 1 0
Duplex Rentals - Big Pine Key
2 Bedroom(s) 1.0 Bath  Sleeps: 4
Starting at: $2,600.00/Mo
Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced for pr... read more »
Angelfish Cove 0
Vacation Home Rentals - Big Pine Key
3 Bedroom(s) 2.5 Bath  Sleeps: 6
Starting at: $3,600.00/Mo
Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Key... read more »
Island Time (Both Halves of Duplex 0
Duplex Rentals - Big Pine Key
5 Bedroom(s) 2.0 Bath  Sleeps: 10
Starting at: Call for Rates
Truly remarkable Big Pine Key vacation home. Rare Duplex on over ½ acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family vacation destination in the Keys. Fully fenced f... read more »
Atlantis 0
Vacation Home Rentals - Big Pine Key
3 Bedroom(s) 3.0 Bath  Sleeps: 6
Starting at: $3,225.00/Mo
Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords direct access to the Content Keys on the Gulf, for diving and snorkeling or quick access to the Atlantic for big sport fish. Just... read more »
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