Vacation Rentals & Apartments in Big Pine Key

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42 apartments

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$253

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$258

Water's Edge

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$171

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Breeze Swept

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$268

Island Time 1 (half of duplex)

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$141

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

Island Time (both halves of duplex)

Big Pine Key house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$236

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$114

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$287

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$775

Palmetto Retreat

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$144

Great rentals within 20 miles that match your search

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$622

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$501

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$655

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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Price per night from

$689

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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Price per night from

$766

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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Price per night from

$287

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$208

Beautiful Home on the Water

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$327

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$231

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$184

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$174

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$234

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$384

"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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Price per night from

$984

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 24 minutes

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Price per night from

$402

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$517

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$700

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$792

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

$573

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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Price per night from

$800

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$743

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$457

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$757

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$328

Waterfront Haven House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$457

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,030

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 2 hours 26 minutes

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Price per night from

$544

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rentals in Big Pine Key

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