Vacation Rentals & Apartments in Big Pine Key

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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

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

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$252

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$218

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

$773

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

$170

Great rentals within 20 miles that match your search

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$153

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$2,209

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$654

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

$352

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

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Price per night from

$320

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

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

$790

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$621

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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Price per night from

$1,145

Salty Retreat

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$447

Buccaneer Boathouse

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$140

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

$687

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

$764

"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

$982

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,030

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Price per night from

$210

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Price per night from

$228

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Price per night from

$332

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

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

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Price per night from

$773

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,718

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$177

Coconut Cay

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$207

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$378

Pelican Perch

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$183

Sailfish Manor

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$383

Grouper Therapy

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$213

Latitude Adjustment

Little Torch Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$173

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$224

Keys Life

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$233

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$230

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