Vacation Rentals & Apartments in Big Pine Key

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29 apartments

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

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

Match: Private outdoor pool (unheated)

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Price per night from

$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

Match: Private outdoor pool (unheated)

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Price per night from

$179

Great rentals within 20 miles that match your search

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated)

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Price per night from

$500

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$2,209

$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

Match: Private outdoor pool (unheated)

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Price per night from

$258

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$602

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$700

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$1,751

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (unheated)

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Price per night from

$1,751

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

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$516

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

Match: Private outdoor pool (unheated)

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Price per night from

$602

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$458

Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$462

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Do

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$168

Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple F

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$174

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private

Sugarloaf Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapi

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$296

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$180

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock &

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$180

Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$180

Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D

Sugarloaf Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$179

Responds fast! avg. 2 hours 34 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$182

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