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

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Big Pine Key

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144 Vacation rentals

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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Responds fast!
avg. 3 hours 21 minutes

from $142 / 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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Responds fast!
avg. 1 hour 51 minutes

from $114 / night

(1) Excellent 

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. 1 hour 12 minutes

from $99 / night

(1) Excellent 

22

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • 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

$1,500 / week

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from $250 / 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

$1,169 / week

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Responds fast!
avg. 3 hours 10 minutes

from $167 / night

(2)  

18

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 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 $322 / night

$2,250 - $2,450 / week

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from $322 / 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

$1,284 / week

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from $184 / 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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from $107 / 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

(1) Excellent 

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

$1,354 / week

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from $194 / 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

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

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 $250 / night

$1,750 / week

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from $250 / 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

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

(10) Excellent 

17

Vacation home in Big Pine Key

Florida Keys / Big Pine Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • 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 $167 / night

$1,167 / week

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from $167 / night

10

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
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 ride under some bridges …see more

from $86 / night

$601 / week

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from $86 / night

(1)  

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
  • Ask about pets
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

$1,400 / week

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from $200 / night