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Big Pine Key Vacation Rentals

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    Travellers to Big Pine Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 26 Rentals in Big Pine Key
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    Reel Paradise - Big Pine Key1 / 17
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Waterfront Home in The Fabulous Florida Keys!1 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Captain Rons Tropical Vacation Hideaway1 / 23
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Keys Caribbean Retreat1 / 10
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 November 2016
    My hubby and I along with sister and bro-in-law had the best time. This cottage is quaint and very clean and has everything you could possibly need. They thought of everything...
    Reviewed 11 July 2016
    We rented this house from Captain Ron and had a great time. We brought a boat and were able to dock it in the canal with no problems. The house was outfitted with everything...
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    About this property
    This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 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
    • Grill
    • Patio
    • 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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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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
    • Wi-Fi
    • Cable/satellite TV
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    • Balcony
    • Air Conditioning
    • Waterfront
    Suitability
    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, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
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    • Washer
    • 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 6 Quick View
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    Pet friendly
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    About this property
    Up dated open home, 2 queen size beds in each room and 2 bath, sleeps 6 confortable with all the comfort of home, warmth and beauty you can desire. WI-FI, cable, complete kitchen with a BBQ on the deck area. Enjoy the peace and tranquility that the Keys life brings you. Water front property,...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable open floor plan coming in from large screen porch and wrap around deck overlooking extra long new dock directly on Bogie Channel. All 4 bedrooms are spacious with two Kings, Queen and twins in the bedrooms all located off a central hall. Large covered area under house and deck for...
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    Big Pine Key, Florida Keys 31581
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    Just picture yourself gazing out at the serene blue waters of the Florida Keys when you stay at Aqua Bella. This beautifully appointed home has 2 ample size bedrooms, a den, dining area and large kitchen for friends and family to gather and plan the day’s tropical activities. The supersized screen...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Cabana in Sunshine Key RV Resort1 / 6
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
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    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2016
    Good RV park with marina.No live bait @ bait shop in marina but had ice, chum and gas.Cabana was clean with fresh sheets and towels.Shower faucet very difficult to work...
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    About this property
    Cabana in beautiful Sunshine Key Resort, Golf Cart,great fishing, breezes, and relaxation. 1 bedrooms, 1 bath, kitchen and living room. Outdoor tiki. enjoy the island living of the Florida Keys. Great resort amenities.Marina available in resort, park your boat, jet sky, and enjoy your vacation...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home is available for you to relax in this peaceful key. This fully fenced gated home is tucked away in unique Port Pines Heights at Big Pine Key. From your large porch you can observe in a way you have never done before, the abundant marine life and native birds in unobstructed...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • 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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    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, 3 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning Florida Keys vacation property offers easy boating access to the Gulf and Oceanside from this well maintained monthly rental, located on Big Pine Key. Spacious and open floor plan makes a great spot for entertaining the group. The large porch with has an outdoor bar for evening...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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
    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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    • Air Conditioning
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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
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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 - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    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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    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 totally remodeled in 2017 with a...
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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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    • Washer
    • Cable/satellite TV
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    • 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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    Open Water with Sunsets, Great Boating and Fishing1 / 10
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Grill
    • Waterfront
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located in Long Beach Estates, one of the most private neighborhoods in the Keys. It is a private peninsula that is cushioned by a large beautiful wildlife preserve with deep water access within minutes to Looe Key. This is a spacious, waterfront home on open water, with a deep...
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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