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House Rentals and Cottages in Big Pine Key, FL

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    Travelers to Big Pine Key are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 13
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 10
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (9) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Big Pine Key, Florida Keys
    5 of 5 stars 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.
    5 of 5 stars Reviewed February 18, 2015
    The first thing that stood out was how clean this place is. Everything is spotless and well organized. A binder was provided with menus, helpful hints about the community and...
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    1 / 6
    3 of 5 stars (1) Average
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    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
    3 of 5 stars 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 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Enjoy this tranquil waterfront house located on a canal in Big Pine Key with easy access to the Flats, Gulf side, Ocean side or an easy boat ride to popular Picnic Island for Sunday Fundays. Launch the Kayaks from the easy step down dock and explore the many canals while fishing or taking in the... View all property information
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    Big Pine Key, Florida Keys
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful home very centrally located in the heart of Big Pine key this 3 bedroom 2 bathroom home is close to everything that lower keys has to offer, Bahia Honda State Park which has one of the most beautiful beaches in the country is only 3.5 miles away as well as 29 miles away from Key West and... View all property information
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    Big Pine Key, Florida Keys
    1 / 10
    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 28 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
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Fully remodeled 2 bed/2 bath home on stilts located near a Nature Preserve for the Endangered Key Deer on Big Pine Key. We have a 50' concrete dock for your own boat or a rental. Our property is completely fenced and is located in a very quiet neighborhood. We do have 2 kayaks, 1 paddle board &... View all property information
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    Big Pine Key, Florida Keys
    1 / 22
    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
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    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
    1 / 16
    1 Bedroom, 1 Bathroom, Sleeps 6 | 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
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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
    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
    1 / 28
    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
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 16
    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
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Fully equipped 3 bedroom 2 bath home on canal. Park your boat right behind the house and head out for your day. This home is located on a very private lot with no neighbors on either side. Bring your RV and boat trailer too, there is plenty of parking for them all. Enjoy sunsets every evening... View all property information
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    Big Pine Key, Florida Keys
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    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
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    Big Pine Key, Florida Keys
    1 / 16
    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,... View all property information
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    Big Pine Key, Florida Keys
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    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
    1 / 5
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy a quite setting on this canal front lot. With its wooded and open area you can enjoy cooking on the charcoal grill. The Home provides a quite place to rest in between shopping, swimming, and dining at restaurants in the near by towns and other key islands. Park your boat in the canal while... View all property information
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    Big Pine Key, Florida Keys
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    1 / 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 7
    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... View all property information
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    Big Pine Key, Florida Keys
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    1 / 12
    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... View all property information
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    Big Pine Key, Florida Keys
    1 / 38
    4.5 of 5 stars (5) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sweet Magnolia is an awesome home on an oversized corner canal with 175' of canal frontage. This property offers lush tropical landscaping, a huge 2nd story lanai overlooking the canals, and privacy galore. You will find everything you need and desire at this home! Each bedroom comes equipped with... View all property information
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    Big Pine Key, Florida Keys
    3 of 5 stars Reviewed 1 week ago
    My wife and I are involved with the vacation rental business. Granted... expectations differ, but in this industry, the highest level of care and promises should be given to the...
    5 of 5 stars Reviewed August 9, 2016
    Our extended family stayed for a week in July, 2016. The house and property more than lived up to every description. This rental home was the best equipped our family has ever...
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    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    MINIMUM 1 MONTH STAY. House is located on a very green, beautiful and quiet neighborhood within National Key Deer Refuge. 7 miles to Bahia Honda State Park, where pristine beaches abound, like Sandspur Beach, voted among the 3 top beaches in Florida by Travel Channel. The house is 30 minutes from... View all property information
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    Big Pine Key, Florida Keys
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Big Pine Key, Florida Keys
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This Island style waterfront cottage is lushly landscaped with unobstructed water views it offers wonderful cham inside and out. 2 bedroom, 1 1/2 bath, outdoor shower, home features vaulted wood ceiling; laundry room/pantry. Kitchen recently updated with new cabinets & Silestone counters. Enjoy a... View all property information
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    Big Pine Key, Florida Keys
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stilt house in Big Pine Key, Florida Keys, 30 miles NE of Key West. 3 BR, 2 full Baths. Kitchen, dining and living area together. Unscreened deck/porch in front. Approx. 1000 sq. feet upstairs.Parking under house and in front. Situated in residential area 7 blocks off Rt.1. Not on water.Park... View all property information
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    Big Pine Key, Florida Keys
    1 / 16
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    980 Sf Moble home on Big Pine Key Fenced lot . 5mins from Baja Honda State park and 25 Mins from Key West. Baja Honda pass comes with rental for the week .Great fishing and snorking .Great Restaurants Neighborhood Park 4 st back . Bikes there to ride. Capt Ron next door for tripes. $750.00 a week... View all property information
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    Big Pine Key, Florida Keys
    4 of 5 stars Reviewed May 17, 2016
    Our family of 3 stayed at Kenny's place the first week of May and it was better than I had hoped. Booking was easy and Kenny responded quickly to phone calls and emails. The home...
    4 of 5 stars Reviewed January 27, 2016
    This was our first time renting this home away from home. It was clean, very well stocked for everyday necessities! Close to shopping and 40 minutes from Key West! We had a...
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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.