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.

Little Gasparilla Island Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    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}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $254 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Little Gasparilla Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 18 Rentals in Little Gasparilla Island
    Sort by:
    Default
    Gulf Front Beach Condo (Little Gasparilla Island)1 / 38
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travelers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Hibiscus House - Beachfront Bliss on the Gulf!1 / 33
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Relaxing Private Island House (LGI)1 / 28
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    RoseMary's Beach House: Beachfront Elegance1 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2016
    If you are looking for an island that is a world away from the hustle and bustle of life and your typical beach resort establishments, then Little Gasparilla Island is for you...
    See all reviews
    About this property
    RoseMary's Beach House is a small jewel of a beach house! It is located directly on the beach, with unparalled views and access to the water. Your front deck literally sits right on the beach! Inside, this home is a gem....designer furnishings with tropical flair, high ceilings, state of the art...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Star Beach House is a glorious beach-front house overlooking the beautiful Gulf of Mexico. It comes fully stocked with everything you need for a great beach vacation, including a kayak, beach floats, fishing gear and beach toys. Please note that this house is on LITTLE GASPARILLA which is not...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Inquiry
    Island Home Retreat PRIVATE DOCK Free Kayaks Free Wi-Fi1 / 13
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 2018
    Thank you to the owner for allowing us to enjoy as little piece of your paradise. The pictures in the advertising are just the way it actually looks, I just took #7 for...
    Reviewed January 29, 2018
    I am the sister of Rachel.. Can't say enough great things about this property... so much space and so comfortable.. kitchen was so well equipped, had everything you need.. the...
    See all reviews
    About this property
    View of The Bay from the front porch.. 1200 square foot living area. Creatively decorated very comfortable. All the conveniences of home yet surrounded by the pristine natural elements of a remote island community. Spacious kitchen, dining and living room, cathedral ceilings, french doors open to a...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Lucky Me ! A Waterfont Retreat1 / 42
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Internet Access
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 2017
    After several years, my husband and I were finally able to getaway for a relaxing couple of days. And the best part is that our puppies were able to come join us on our vacation...
    Reviewed April 15, 2017
    No cars allowed. That's right park your car accross the bay and take a short boat ride to your little vacation house. I had a great time with my son and his bride to be and lets...
    See all reviews
    About this property
    This lovely 2 story home is situated right on the Bay. Arrive at your own private dock Walk past new outdoor shower, to front porch to enjoy serene view of bay. Lucky Me is tiled thru-out, and features spacious master bedroom with king size bed, large walk-in closet, complete with hanging and...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Inquiry
    Coconut Hideaway: Gulf-Front Dream House!1 / 46
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Waterfront
    • Washer
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2017
    This place is truly paradise on Earth. My family and I stayed at Coconut Hideaway the first week of June (2017) and everything about our stay was perfect. This beach house was...
    Reviewed May 3, 2016
    What a wonderful property. The island itself is nothing but restful and a great place to decompress. Coconut Hideaway was everything it advertised.Roomy with several levels for...
    See all reviews
    About this property
    COCONUT HIDEAWAY is one of the most charming and unique homes on the island. This is our private home -- not a 'rental unit' -- and we have decorated it with antiques, oriental carpets, original artwork and many collections from our travels abroad. Our Caribbean-inspired home is built in the 'Old...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AKA the 'Green Roof Condos', we are a 1000 sq ft end unit with no one above or below. South facing and perched 20 feet above the ground with palm trees in all views. There is a second floor loft (fixed ladder) that sleeps 2. We have a freshwater pool right on the island. The unit has bamboo...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Serenity Cottage  on Little Gasparilla Island1 / 22
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Air Conditioning
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 7, 2018
    The house is clean. The house is close to dock and beach. The kitchen is well stocked. The staff is very help full. Thanks for a great winter vacation.
    See all reviews
    About this property
    Serenity Cottage is an oasis of peace and privacy located on one of Florida's most beautiful barrier islands. This lovely cottage is a respite from the hustle and bustle and is just a short walk to the beach or the bay....for the best of both worlds when it comes to island living. Please note...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    Save time - get the best Little Gasparilla Island rentals sent straight to your email!
    Get the List
    BEACHFRONT | Beautiful | Relaxing Views of the Gulf | Little Gasparilla Island1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2017
    We could not have asked for a better condo in a better location EVER. As soon as we got on the ferry over to the island I felt a weight off of my shoulders and walking into the...
    Reviewed June 18, 2017
    Very nice condo, updated and everything was clean and current. Manager and owners were good about responding to messages. The island is very natural so if this is not your thing...
    See all reviews
    About this property
    Step inside “SeaScape” and enjoy breathtaking, panoramic views of the Gulf. This beachfront condo is a corner unit and one of the few direct gulf front units at the Placida Beach Club. The area is a romantic paradise located on Little Gasparilla Island. It is a tropical barrier island,...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    'The Round House' - An Island Original!1 / 74
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Ocean Views
    • Porch
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2016
    Just got back from the best week ever! The house was beautiful and had the most amazing views! Brett's Taxi was the best getting us from the dock to the house on his golf cart...
    Reviewed March 17, 2016
    We stayed for two weeks in February and had a wonderful relaxing vacation. The Round House offers views of the ocean from inside the kitchen and living riooms, and sitting on...
    See all reviews
    About this property
    This classic island house has been a fixture on Little Gasparilla Island for over 30 years. The new owners have lovingly redecorated and renovated the interior while keeping the quaint charm of the original 'round' design. Everything has been updated, with new steps and new impact resistant...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Inquiry
    Coconut Palm Cottage - Tropical Beach Getaway1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Cable/satellite TV
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coconut Palm Cottage is brand new to the rental market! This charming home has been lovingly maintained by one owner for years. The lovely tropical foliage and well maintained yard attests to the care and love lavished on this little cottage. Now it is available for YOUR family vacation....
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Make Inquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Home is located on a remote island. *A local water taxi or boat is needed to get to island. *NO Cars on island, they are parked off island at a local marina. *Private, secluded beaches. *No commercial establishments on Little Gasparilla Island. *Grocery shopping is off the island. *Kayaks and...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful beach home is the perfect place to stay at this amazing island getaway! The open floor plan is filled with fun and cheerful decorations and comfortable furnishings. This 3 bedroom 2.5 bath, plus loft can sleep 10 comfortably and has something fun for everyone. Features include Flat...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Inquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Ocean Views
    • Terrace
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 'La Te Da' house is a two story key west style home located directly on the Gulf of Mexico. The backyard is a private beach, you are simply foot steps away from beautiful turquoise water and sandy beach. We are next to Boca Grande, which is known for the world famous tarpon fishing tournaments....
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Air Conditioning
    • Terrace
    • Ocean Views
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Angler's Paradise is located on beautiful Little Gasparilla Island, one of the most pristine barrier islands in Florida. This island has no bridge and can only be reached via private boat or water taxi, which means that your stay here will be one of peace and tranquility and some of the best...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Inquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Hot Tub
    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and relaxing waterfront condo ready for you to enjoy and make nice memories! Come watch the dolphins each day from the porch as you sip your coffee in the morning, or be on the lookout for the local manatee that swims these waters. They say he's as big as a Volkswagen! Don't forget to...
    View all property information
    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry

    Additional Little Gasparilla Island Info

    Go to map view
    • Local time: 08:02 AM (EDT)
    List your property
    Owner log in