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Big Pine Key Vacation Rentals

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    Travelers to Big Pine Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 26 Rentals in Big Pine Key
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Keys Caribbean Retreat1 / 10
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    RV Lifestyle, close to Key West1 / 13
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reel Paradise - Big Pine Key1 / 17
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
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    Pet friendly
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    Reviewed March 13, 2017
    Very nice house.Everything is kept immaculate.The house is very roomy and well stocked.The grounds are beautiful.There is a nice spot to relax or cookout by the canal.The owner...
    Reviewed August 5, 2015
    This is a great place to enjoy the lower keys. Extremely clean and well appointed. We stay there as often as we can. I can't wait to go back.
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    About this property
    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 a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large...
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    Big Pine Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 20, 2016
    We just returned from a fabulous vacation at this house. It was so relaxing, the views were awesome. We saw so many kinds of birds. It is absolutely a perfect place to enjoy...
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    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood....
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    Big Pine Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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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    Big Pine Key, Florida Keys 33043
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    • Wi-Fi
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    • Waterfront
    • Balcony
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    Pet friendly
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    Smoking allowed
    Reviewed November 29, 2016
    We couldn't have been happier with staying at his home in Big Pine. The view from the upper deck is beautiful and everything we expected when we rented the home. It's about 40...
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    About this property
    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 a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway....
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    Big Pine Key, Florida Keys 33043
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Waterfront
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    Pet friendly
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Balcony
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Waterfront
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    Rental Home - 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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 2, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    Rental Home - 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)
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    • Private Yard
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Big Pine Key Vacation Rental

    Big Pine Key and its neighboring islands are some of the most popular vacation destinations for families who want to rent a beachfront house or condo. The climate in this part of Florida is delightful and very similar to the warm and pleasant climates of the Caribbean. The crystal blue waters and the white sandy beaches in Big Pine Key make this an impressive location for your next vacation rental.

    Things to Do

    Big Pine Key is a fantastic place to come if you want to get away from all the troubles and stress of day-to-day life. The vacation houses and condos available here are designed for rest and relaxation. The main appeal of Big Pine Key is the tranquil environment and beautiful scenery. There are plenty of outdoor activities that you can enjoy when you’re not in your rental home, such as fishing, walking and biking, and seeking out wildlife.

    Many people visiting Big Pine Key enjoy getting out into the ocean for excellent snorkeling and diving. Looe Key is located approximately 7 miles off shore and provides the perfect location to see stunning sea life. It is widely regarded as one of the clearest and best reefs for snorkeling and diving in the Keys.

    Family Fun

    If you’re visiting Big Pine Key with children, there are numerous wonderful activities that will get them out of the rental home for the day. The Theater of the Sea and the National Key Deer Refuge are great options for the whole family. If you would like to spot some of the many alligators that reside in the area, then you should head to the Blue Hole.

    Delicious Dining in Big Pine Key

    If you’re staying in a vacation home in Big Pine Key, you may choose to dine in and enjoy a quiet intimate or pizza with the family. There are many local groceries where you can purchase fresh seafood and produce to prepare a meal in your condo or villa. However, if you do fancy a meal out, you can take a trip to Rob’s Island Grill, The Big Pine Restaurant, or The China Garden. All of these restaurants are local and provide culinary delights.

    Benefits of Big Pine Key Rentals

    Unlike a hotel, staying in a Big Pine Key vacation rental provides you with complete privacy and tranquility during your vacation. Enjoy the space and security you can get from your own beautiful rental home.

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