25 Best Big Pine Key Vacation rentals on Holiday Lettings - House rentals

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29 Vacation rentals

13

Home accommodation in Big Pine Key

Florida Keys / Big Pine Key

3 10 30 nights min

  • 3 bedrooms
  • Sleeps 10
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Beautifully decorated 3 bed/2 bath canal front home located in Big Pine Key. Master bedroom with queen bed and attached master bathroom. Newly renovated master bathroom has a walk in shower. Second guest bedroom has plush queen bed. Third guest bedroom has a queen/full …see more

from $130 / night

$910 / week

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from $130 / night

(11) Excellent 

23

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
A quite, private, waterfront residence in the lower Florida Keys, the American Caribbean. Decorated in Nautical and Tropical décor. Undeveloped property on one side and across the canal. On a boating canal with dockage for your boat, Free launching at the nearby marin …see more

from $90 / night

$975 / week

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from $90 / night

19

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Air conditioning
Comfortable open floor plan coming in from large screen porch and wrap around deck overlooking extra long new dock directly on Bogie Channel. All 4 bedrooms are spacious with two Kings, Queen and twins in the bedrooms all located off a central hall. Large covered area u …see more

from $167 / night

$1169 / week

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from $167 / night

27

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

5 10 30 nights min

  • 5 bedrooms
  • Sleeps 10
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Truly remarkable Big Pine Key vacation home. Rare Duplex on over an 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 privacy and lots of yard …see more

from $184 / night

$1284 / week

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from $184 / night

(3) Excellent 

11

Apartment rental in Big Pine Key

Florida Keys / Big Pine Key

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 8 mi
  • Child friendly
  • Air conditioning
Welcome to your Big Pine Getaway! Enjoy everything Key West has to offer and the quiet evenings of Big Pine. Only a short 25 minute drive to Key West, and less than 10 minutes to the beautiful beaches of Bahia Honda State Park. You are also a quick 15 minute drive nort …see more

from $99 / night

$680 / week

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Responds fast!
avg. 58 minutes

from $99 / night

(1) Very Good 

27

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40" flat screen TV, and the guest room is equipped with a very s …see more

from $275 / night

$1925 / week

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Responds fast!
avg. 2 hours 24 minutes

from $275 / night

15

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Truly remarkable Big Pine Key vacation home. Rare Duplex on over an 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 privacy and lots of yard …see more

from $87 / night

$607 / week

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from $87 / night

(10) Excellent 

17

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family r …see more

from $200 / night

$1400 - $1600 / week

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from $200 / night

28

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

4 12 30 nights min

  • 4 bedrooms
  • Sleeps 12
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
28 DAY MINIMUM RENTAL. WE WILL NOT RESPOND TO REQUESTS FOR LESS THAN 28 DAYS. Thank you. Sit back and enjoy the breezes from poolside on the open water of Bogie Channel. Enjoy tranquil open water views from this charming ground level home. This home comes complete with …see more

from $240 / night

$1680 / week

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from $240 / night

(9) Excellent 

10

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Child friendly
This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of c …see more

from $96 / night

$980 - $1190 / week

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from $96 / night

17

Big Pine Key Vacation home rental

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
This stunning Florida Keys vacation property offers easy boating access to the Gulf and Oceanside from this well maintained monthly rental, located on Big Pine Key. Spacious and open floor plan makes a great spot for entertaining the group. The large porch with has an o …see more

from $94 / night

$654 / week

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from $94 / night

16

Big Pine Key Vacation home rental

Florida Keys / Big Pine Key

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Great boating access, dockage. Renovated with granite countertops, custom cabinetry, tumbled marble bathroom, 1 Bedroom with a Loft. Will sleep up to 6 people. Located at Mile Marker 27, Conveniently located between Key West and Marathon. Within minutes of popular resta …see more

from $142 / night

$994 / week

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from $142 / night

(1) Excellent 

19

Vacation home with swimming pool in Big Pine Key

Florida Keys / Big Pine Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quie …see more

from $268 / night

$1875 / week

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from $268 / night

(1) Good 

6

Vacation caravan/mobile home rental

Florida Keys / Big Pine Key

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Cabana in beautiful Sunshine Key Resort, Golf Cart,great fishing, breezes, and relaxation. 1 bedrooms, 1 bath, kitchen and living room. Outdoor tiki. enjoy the island living of the Florida Keys. Great resort amenities.Marina available in resort, park your boat, jet sky, …see more

from $250 / night

$1250 / week

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from $250 / night

14

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts decor by an award winning Key West decorator. Includes fast access Internet for you to surf the internet quickly in addition to a large screen TV. Enjoy a swim in the …see more

from $194 / night

$1354 / week

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from $194 / night

(1) Excellent 

8

Vacation home rental

Florida Keys / Big Pine Key

3 11 1 night min

  • 3 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Tiki Beach is a 3 bedroom, 2 bath bungalow located on the Gulf side of the island of Big Pine Key. Over an acre and a half with 150 ft of open water frontage and a private pool, hot tub and lighted dock that allows for a boat with up to a 3 foot draft at average tide l …see more

from $450 / night

$3150 / week

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from $450 / night

(1) Excellent 

22

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck …see more

from $250 / night

$1500 - $2000 / week

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from $250 / night

16

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children
Welcome to the Lazy Manatee. We are located on Big Pine Key,Fl. Our passion is to provide a place to relax while enjoying all the wonders of the Florida Keys. Big Pine is home to the famous Key Deer, an endangered species that can be seen throughout this area. The Lazy …see more

from $250 / night

$1500 / week

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from $250 / night

16

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
A get away to "Our Island Thing" will be unforgettable vacation for everyone. Huge 1,900 square-foot house with lots of room for the whole family and kids. Four bedrooms and two bathrooms, this two level concrete home is roomy and airy. The second floor has a huge kitch …see more

from $200 / night

$1400 / week

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from $200 / night

(2)  

18

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Just picture yourself gazing out at the serene blue waters of the Florida Keys when you stay at Aqua Bella. This beautifully appointed home has 2 ample size bedrooms, a den, dining area and large kitchen for friends and family to gather and plan the day’s tropical activ …see more

from $55 / night

$385 / week

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from $55 / night

12

Home rental in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
What better get- a-way vacation than to get "Lost in Paradise". The location is a little off the beaten path to ensure wonderful privacy. Fully fenced, pet friendly and a wonderful pool area to lounge in the Florida Keys sunshine. This superb home has just been totally …see more

from $133 / night

$931 / week

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from $133 / night

16

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Truly remarkable Big Pine Key vacation home. Rare Duplex on over an 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 privacy and lots of yard …see more

from $94 / night

$654 / week

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from $94 / night

16

Big Pine Key Vacation home rental

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Kick back and relax at Keys Breeze! This super comfortable 2 bedroom, 2 bathroom stilt home offers easy living with a huge screened porch overlooking, the crystal clear canals and distant bay views. The cedar beam ceilings give a feeling of old keys charm, beautifully d …see more

from $94 / night

$654 / week

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from $94 / night

7

Big Pine Key Vacation home rental

Florida Keys / Big Pine Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
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 a quick motor to Ba …see more

from $104 / night

$724 / week

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from $104 / night

16

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This house is in a very quiet section of a quiet island . It is surrounded by palm trees. There is a large screened deck which catches the breeze. At the end of the canal (approximately a block ) you will be in a large open area between Big Pine and Little Torch ; from …see more

from $107 / night

$747 / week

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Responds fast!
avg. 3 hours 49 minutes

from $107 / night

8

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
  • Pet friendly
Up dated open home, 2 queen size beds in each room and 2 bath, sleeps 6 confortable with all the comfort of home, warmth and beauty you can desire. WI-FI, cable, complete kitchen with a BBQ on the deck area. Enjoy the peace and tranquility that the Keys life brings you. …see more

from $110 / night

$770 / week

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Responds fast!
avg. 3 hours 58 minutes

from $110 / night

(1) Excellent 

9

Vacation caravan/mobile home in Big Pine Key

Florida Keys / Big Pine Key

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden
The FL Keys is Monroe County. B&B's and the like are not legal here (to rent less than 28 days) so we don't. We let our guest, (individuals and couples) stay up to 2 nights free, with the purchase of a one hour $250 boat tour. It is a certain win / win. One should alway …see more

from $125 / night

$875 / week

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Responds fast!
avg. 1 hour 45 minutes

from $125 / night

10

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Air conditioning
Nice Quiet 2 bedroom 2 bath beach cottage located oceanside of US 1 on a swimming canal next to open water canal. Sunset and open water view. Boat slip to open water next door by same owner. New Kitchen and all furnishings 2010. Close to all shopping and activities On …see more

from $114 / night

$800 / week

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from $114 / night

20

Big Pine Key Vacation home rental

Florida Keys / Big Pine Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
This waterfront vacation home is located in a quiet nature reserve, surrounded by several open undeveloped lots for extra privacy. Beautifully decorated 3 bedroom, 2 bath home with florida screen porch, and plenty of outdoor living area underneath. Master bedroom featur …see more

from $99 / night

$693 / week

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Responds fast!
avg. 47 minutes

from $99 / night