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Big Pine Key Vacation Rentals

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    Travelers to Big Pine Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 23
    5 of 5 bubbles (11) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The FL Keys is Monroe County. B&B's and the like are not legal here (to rent less than 28 days) so we don't. We let our guest, (individuals and couples) stay up to 2 nights free, with the purchase of a one hour $250 boat tour. It is a certain win / win. One should always get on the water when... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 10
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed November 20, 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...
    5 of 5 bubbles Reviewed July 11, 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 we...
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    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Big Pine Key, Florida Keys 33042
    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Big Pine Key, Florida Keys 31581
    1 / 105
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Modern, clean, and cozy 2 beds/1 bath bunk house accommodating up to 6 guests located on a full amenity resort and marina with provided towels and linens. Unit includes a full kitchen set up with provided kitchenware, coffee pot, toaster, dishes, and utensils. Equipped with TV, cable TV, one double... View all property information
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    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed March 28, 2017
    Beautiful relaxing friendly people very clean and comfy kids and pets friendly. We had an awesome time. We liked it so much that we booked again for June. Love it and the host are...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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.... View all property information
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    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles 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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    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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,... View all property information
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    Big Pine Key, Florida Keys 33043
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    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 8
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Tiki Beach is a 3 bedroom, 2 bath bungalow located on the Gulf side of the island of Big Pine Key. Over an acre and a half with 150 ft of open water frontage and a private pool, hot tub and lighted dock that allows for a boat with up to a 3 foot draft at average tide levels. Water supply on dock... View all property information
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    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed January 20, 2017
    This place was perfect for our family! Location and amenities were incredible, we will be back!!!!!!
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    1 / 6
    3 of 5 bubbles (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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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... View all property information
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    Big Pine Key, Florida Keys 33043
    3 of 5 bubbles Reviewed August 16, 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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    1 / 26
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40' flat screen TV, and the guest room is equipped with a very sturdy wood bunk bed with a... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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.... View all property information
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    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles 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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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Big Pine Key, Florida Keys 33043
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Big Pine Key, Florida Keys 33043
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Big Pine Key, Florida Keys 33043
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Big Pine Key, Florida Keys 33043
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    WINTER SPECIAL: For the winter season of December 2016 through February 2017, enjoy discounted rates on a stay at Diver's Delight! Celebrate the coming winter season with an oceanside getaway. Book your stay today! Sit back and enjoy the breezes from poolside on the open water of Bogie Channel.... View all property information
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    Big Pine Key, Florida Keys 33043
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Big Pine Key, Florida Keys 33043
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    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... View all property information
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    Big Pine Key, Florida Keys 33043
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    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Welcome to the Lazy Manatee. We are located on Big Pine Key,Fl. Our passion is to provide a place to relax while enjoying all the wonders of the Florida Keys. Big Pine is home to the famous Key Deer, an endangered species that can be seen throughout this area. The Lazy Manatee is a spacious 2... View all property information
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    Big Pine Key, Florida Keys 33043
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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... View all property information
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    Big Pine Key, Florida Keys 33043
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Big Pine Key, Florida Keys 33043
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Big Pine Key, Florida Keys 33043
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 16
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 15
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    Big Pine Key Flight and Weather Info
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    Additional Big Pine Key Info

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    • Local time: 08:53 AM (EDT)
    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.