Vacation Rentals & Apartments in Big Pine Key

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126 apartments

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Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$253

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$141

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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$236

Our Island Thing

Big Pine Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$278

Island Time 2 (half of duplex)

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$148

Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$268

Responds fast! avg. 2 hours 34 minutes

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$119

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$115

Responds fast! avg. 2 hours 34 minutes

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$179

Castaway On The Keys: Experience Spectacular Open Water Living on Bogie Channel,

Big Pine Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$258

Responds fast! avg. 2 hours 34 minutes

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$179

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$171

Responds fast! avg. 2 hours 34 minutes

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$126

Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

Great rentals within 20 miles that match your search

Bay Pointe

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$204

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$258

Blue Lagoon

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$318

Casa Turquesa

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$288

Cove Isles

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$198

Lafitte Landing

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$144

Manatee Bay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$151

Quiet Waters

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Margarita Villa

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$189

Pirate's Cove

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$118

South Point Shores

Sugarloaf house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$231

Villa Cayo

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$414

St. Croix

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$121

Coral House

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Big Torch Retreat

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$164

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$655

Pirates Pointe

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$174

Reef Resort - Peaceful Getaway 204

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

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Price per night from

$353

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

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Price per night from

$320

Island Chalet

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

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Price per night from

$327

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

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Price per night from

$574

Viewing 38 of 126
rentals in Big Pine Key

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