We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

House Rentals and Cottages in Big Pine Key, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $173 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Travelers to Big Pine Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $313
    / Night
    View Details
    View Details
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $149
    / Night
    Payment Protection
    View Details
    View Details
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $250
    / Night
    Payment Protection
    View Details
    View Details
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    From
    $250
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Grill
    • Waterfront
    • Balcony
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 12
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    From
    $139
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A quite, private, waterfront residence in the lower Florida Keys, the American Caribbean. Decorated in Nautical and Tropical décor. Undeveloped property on one side and across the canal. On a boating canal with dockage for your boat, Free launching at the nearby marina and space for your boat... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed December 20, 2015
    My wife and I were looking for a place on the water that was quiet, comfortable and inexpensive. Captain Ron provided all of that and more. The house is the perfect getaway and...
    5 of 5 stars Reviewed June 5, 2015
    Everything that is promised by the landlord was delivered. The house was very clean, comfortable, & is located in a quiet neighborhood. We loved having accommodations that...
    See all reviews
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    From
    $125
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33042
    1 / 5
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $2,000
    / Night
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Grill
    • Waterfront
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    4 of 5 stars Reviewed January 12, 2012
    Having enjoyed traveling the length of the Keys near about every one of the past 45 years, I have never really had a chance to really experience the Keys as I did from this unique...
    See all reviews
    1 / 16
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $125
    / Night
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    • Satellite TV
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    4 of 5 stars Reviewed 1 week ago
    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...
    4 of 5 stars Reviewed November 2, 2015
    Would go back very relaxing spouse and out of town in-laws came in for the fantasy fest picked up transportation at the end of the block and we're returned nice and safe at days...
    See all reviews
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
    From
    $173
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 10
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $139
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed July 30, 2015
    This was our first experience renting a house for our vacation instead of a hotel AND one of our best vacation decisions we've ever made. The house was great and Captain Ron and...
    5 of 5 stars Reviewed May 31, 2015
    My husband and I came to Big Pine Key for a second honeymoon. We immediately fell in love with the house and the atmosphere. Very clean and cozy! We had a fantastic time and...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $167
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Parking
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
    Location Information
    Big Pine Key, Florida Keys 31581
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $114
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Wi-Fi
    • Satellite TV
    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $1,000
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Washer
    • Waterfront
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 17
    5 of 5 stars (9) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    From
    $200
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Waterfront
    • DVD Player
    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    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...
    See all reviews
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $175
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • DVD Player
    • Grill
    • Private Yard
    • Satellite TV
    • Parking
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located on a RV resort with heated pool, across the street from a marina to keep you boat. Close to one of the best beaches in tht Florida Keys and the world, Bahia Honda, parks and many restaurants. The bathrooms and laundry room is located one lot away, pool about 50ft away, located between... View all property information
    Location Information
    Big Pine Key, Florida Keys 33040
    1 / 38
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $1,500
    / Week
    View Details
    View Details
    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed December 24, 2015
    Spent a week here in early December. Very nice, roomy with great lanai overlooking the junction of two canals. The neighbors were very friendly and helpful with ideas for the best...
    5 of 5 stars Reviewed October 8, 2015
    First of all, the ambiance of this place was awesome! Was a really nice getaway and immediately had that Peaceful, I really like it here feeling for both the neighborhood and the...
    See all reviews
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $133
    / Night
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $83
    / Night
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    • Air Conditioning
    • Parking
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other traveler has booked this property
    From
    $225
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Private Yard
    • Patio
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $83
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    Get the List
    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.