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  • Reel Paradise - Big Pine Key

    Big Pine Key, Florida

    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in... ...more

    Beds: 3 Baths: 3 Property type: House (10) Exceptional
    $140 / Nightly
  • Blue Heron

    Big Pine Key, Florida

    Nice and comfortable 2 bedroom, 2 bathroom vacation home on Big Pine Key in the Eden Pines area. This vacation rental is neat and clean with a 40' wood boat dock and fish cleaning area to clean all... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $93 / Nightly
  • Breeze Swept

    Big Pine Key, Florida

    Magnificent open water views in this beautiful 3 Bedroom, 2 bath home on Big Pine Key! This home boasts decor by an award winning Key West decorator. Includes fast access Internet for you to surf... ...more

    Beds: 3 Baths: 2 Property type: House (1) Exceptional
    $197 / Nightly
  • Island Time 1 (half of duplex)

    Big Pine Key, Florida

    Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family... ...more

    Beds: 2 Baths: 1 Property type: House (0)
    $94 / Nightly
  • Island Time 2 (half of duplex)

    Big Pine Key, Florida

    Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family... ...more

    Beds: 3 Baths: 1 Property type: House (0)
    $100 / Nightly
  • Island Time (both halves of duplex)

    Big Pine Key, Florida

    Truly remarkable Big Pine Key vacation home. Rare Duplex on over an acre in the Doctors Arm area. A huge boat basin and direct access to Bogie channel. Rent one or both sides for the best family... ...more

    Beds: 5 Baths: 2 Property type: House (0)
    $197 / Nightly
  • Our Island Thing

    Big Pine Key, Florida

    A get away to "Our Island Thing" will be unforgettable vacation for everyone. Huge 1,900 square-foot house with lots of room for the whole family and kids. Four bedrooms and two bathrooms, this two... ...more

    Beds: 4 Baths: 2 Property type: House (1)
    $200 / Nightly
  • Sunrise Drive

    Big Pine Key, Florida

    Sunrise Drive, the perfect 3 bedroom, 3 bath home for your stay in the Florida Keys. It is located in Tropical Bay Estates, a quiet upper scale community with water access throughout. A perfect... ...more

    Beds: 3 Baths: 3 Property type: House (0)
    $358 / Nightly
  • Waterfront Home in The Fabulous Florida Keys!

    Big Pine Key, Florida

    PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes... ...more

    Beds: 2 Baths: 2 Property type: House (3)
    $250 / Nightly
  • Big Pine 2/2 ,Water Views

    Big Pine Key, Florida

    Nice Quiet 2 bedroom 2 bath beach cottage located oceanside of US 1 on a swimming canal next to open water canal. Sunset and open water view. Boat slip to open water next door by same owner. New... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $114 / Nightly
  • Fisherman's Paradise in the Heart of Big Pine Key

    Big Pine Key, Florida

    This waterfront vacation home is located in a quiet nature reserve, surrounded by several open undeveloped lots for extra privacy. Beautifully decorated 3 bedroom, 2 bath home with florida screen... ...more

    Beds: 3 Baths: 2 Property type: House (1) Exceptional
    $99 / Nightly
  • Florida Keys Fisherman and Divers Paradise

    Big Pine Key, Florida

    28 DAY MINIMUM RENTAL. WE WILL NOT RESPOND TO REQUESTS FOR LESS THAN 28 DAYS. Thank you. Sit back and enjoy the breezes from poolside on the open water of Bogie Channel. Enjoy tranquil open water... ...more

    Beds: 4 Baths: 4 Property type: House (0)
    $250 / Nightly
  • Lost In Paradise

    Big Pine Key, Florida

    What better get- a-way vacation than to get "Lost in Paradise". The location is a little off the beaten path to ensure wonderful privacy. Fully fenced, pet friendly and a wonderful pool area to... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $140 / Nightly
  • 3 bedroom canal front home minutes from open Water!

    Big Pine Key, Florida

    Beautifully decorated 3 bed/2 bath canal front home located in Big Pine Key. Master bedroom with queen bed and attached master bathroom. Newly renovated master bathroom has a walk in shower. Second... ...more

    Beds: 3 Baths: 2 Property type: House (0)
    $150 / Nightly
  • Hideaway Bay

    Big Pine Key, Florida

    Come hideaway with us in the beautiful Florida Keys at Hideaway Bay. Located in the Port Pine Heights area of Big Pine Key with quiet streets and where our cute Key Deer roam every evening.... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $109 / Nightly
  • Caribbean Cove

    Big Pine Key, Florida

    Come to relax in one of Big Pine's most peacefully secluded waterfront retreats! Surrounded by the Key Deer Preserve. Tastefully decorated with favorable Key West colors. Very clean, freshly... ...more

    Beds: 2 Baths: 2 Property type: House (0)
    $86 / Nightly
  • New Listing! Beautiful Canal front , Key Deer and jacuzzi.

    Big Pine Key, Florida

    -Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - Boat lift , dock and fish cleaning station. -Excellent access to Atlantic and... ...more

    Beds: 3 Baths: 3 Property type: House (0)
    $150 / Nightly
  • Experience the Keys like a Local at this Spacious Canal Front Home with Dock!

    Big Pine Key, Florida

    This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to... ...more

    Beds: 3 Baths: 3 Property type: House (0)
    $110 / Nightly
  • Unwind at a waterfront home, a short drive to fun, shops, dining & 30min to Key

    Big Pine Key, Florida

    This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 30 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to... ...more

    Beds: 2 Baths: 1 Property type: House (0)
    $119 / Nightly
  • Beautiful Partial Bay View Florida Keys Home With lap pool 60 feet long

    Big Pine Key, FL

    This property is the ideal Fisherman/ boater/diver paradise. You are only five miles from the beautiful Looe Key National Reef preserve which is great for diving and snorkeling. Also, the area... ...more

    Beds: 3 Baths: 2 Property type: House (1) Exceptional
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Search result 1 to 20 Of 67

Big Pine Key: Vacation Rental By Owner

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Big Pine Key. Many accommodations in Big Pine Key provide "Non Smoking Only", there are 44, or there are 37 of Vacation Rentals in Big Pine Key with a "Fishing", there are also 36 with "Waterfront -Water View", which is another great reason to visit Big Pine Key.