Vacation Rentals & Apartments in Big Pine Key

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100 apartments

Charming Elevated Waterfront Home

Big Pine Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$253

Responds fast! avg. 2 hours 34 minutes

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$119

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$115

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$126

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$179

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

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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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

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$179

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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$258

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$179

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

Great rentals within 20 miles that match your search

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$655

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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$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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$574

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$500

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

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$1,147

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$983

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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$802

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,031

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$688

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$765

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$458

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$448

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$141

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$210

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$333

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$287

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$208

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$178

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$258

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$327

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$379

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$184

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$384

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$214

Sun Kissed

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$158

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$174

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$234

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rentals in Big Pine Key

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