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Big Pine Key House Rentals

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    Travellers to Big Pine Key are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    24 Matching Rentals in Big Pine KeyView all 25 rentals
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    Reel Paradise - Big Pine Key1 / 17
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront Home in The Fabulous Florida Keys!1 / 19
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fisherman's Paradise in the Heart of Big Pine Key1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Grill
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 porch, and plenty of outdoor living area underneath. Master bedroom features king bed with attached...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    -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 Gulf, minutes to the best lower keys fishing in country. -Nice Jacuzzi to enjoy the sunset. - 15...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great boating access, dockage. Renovated with granite countertops, custom cabinetry, tumbled marble bathroom, 1 Bedroom with a Loft. Will sleep up to 6 people. Located at Mile Marker 27, Conveniently located between Key West and Marathon. Within minutes of popular restaurants along US 1. Easy...
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    Big Pine Key, Florida Keys 33042
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Balcony
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Kitchen and all furnishings 2010. Close to all shopping and activities On Big pine Key and a short...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 guest bedroom has plush queen bed. Third guest bedroom has a queen/full bunk bed, and if that's not...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 location if you are looking for a tranquil island setting but close to the fun as Key West is only 25...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Air Conditioning
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    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 painted interior/exterior walls and well maintained. This cozy and comfortable décor will make you feel...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
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    • Patio
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 enjoy the party atmosphere of Key West! Dock your boat out back, sip on your favorite drink under the...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 enjoy the party atmosphere of Key West! Dock your boat out back, sip on your favorite drink and grill your...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Balcony
    • Patio
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is in a very quiet section of a quiet island . It is surrounded by palm trees. There is a large screened deck which catches the breeze. At the end of the canal (approximately a block ) you will be in a large open area between Big Pine and Little Torch ; from there you can easily travel...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Everyday is a great day at Atlantis. Beautiful Big Pine home located just minutes to Bogie Channel. This channel affords direct access to the Content Keys on the Gulf, for diving and snorkeling or quick access to the Atlantic for big sport fish. Just a quick motor to Bahia Honda Bridge to play hide...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 that great, fresh fish you're gonna catch. Easy ride under some bridges to Pine Channel with decent...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Breeze Swept1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Internet Access
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 April 2018
    We stayed for the month of March 2018 and absolutely loved this place. Right on the ocean and we took the kayaks out right off the property. The home was very comfortable with...
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    About this property
    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 the internet quickly in addition to a large screen TV. Enjoy a swim in the new, heated pool after a...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 vacation destination in the Keys. Fully fenced for privacy and lots of yard space for everyone to enjoy...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 vacation destination in the Keys. Fully fenced for privacy and lots of yard space for everyone to enjoy...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 vacation destination in the Keys. Fully fenced for privacy and lots of yard space for everyone to enjoy...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick back and relax at Keys Breeze! This super comfortable 2 bedroom, 2 bathroom stilt home offers easy living with a huge screened porch overlooking, the crystal clear canals and distant bay views. The cedar beam ceilings give a feeling of old keys charm, beautifully decorated in soothing tropical...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 level concrete home is roomy and airy. The second floor has a huge kitchen, living and dining area,...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. This home is cozy and comfortable, with 2 bedrooms and 2 bathrooms and has nice plantation style...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 lounge in the Florida Keys sunshine. This superb home has just been nicely updated in 2017. There is a...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Wi-Fi
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    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 views from this charming ground level home. This home comes complete with 10' deep pool on the open...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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