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Pet Friendly Holiday Rentals in Little Gasparilla Island

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    Travellers to Little Gasparilla Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    11 Matching Rentals in Little Gasparilla IslandView all 18 rentals
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    Coconut Hideaway: Gulf-Front Dream House!1 / 46
    (10)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Hibiscus House - Beachfront Bliss on the Gulf!1 / 33
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Serenity Cottage  on Little Gasparilla Island1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Balcony
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2019
    We decided to head down south from Orlando last minute and found the cottage on AirBB. The price was very reasonable given time of year, location and size of the house...
    Reviewed 8 February 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.
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    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...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    'The Round House' - An Island Original!1 / 37
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 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 18 March 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...
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    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...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lucky Me ! A Waterfont Retreat1 / 45
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 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 16 April 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...
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    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...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Coconut Palm Cottage - Tropical Beach Getaway1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Cable/satellite TV
    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....
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Private Garden
    • Balcony
    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...
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    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Outdoor Dining Area
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    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...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beach Front Home. Panoramic sunsets. Unrivaled seclusion!1 / 28
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2019
    We rented the house from owner Ray for 5 nights in March 2019. The house is awesome. It is perfectly located on little Gasparilla with a great view of the ocean. It has...
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    About this property
    Our home is oriented to provide breath-taking, unobstructed, panoramic views of the Gulf from the kitchen/living area, the screened-in dining room/porch, the master bedroom and the top deck suite. Floor-to-ceiling windows across the entire beach-side, provide an infinity effect and the open-plan...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Old Time Florida, the best of many worlds from this unique round beach house on Little Gasparilla Island – the sheer pleasure of relaxation, the elegance of accommodations, the miles of warm clear ocean waters. The Rondavel (pronounced Ron-dah-ville) with its 4,000 square feet of comfy...
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    Location Information
    Little Gasparilla Island, Southwest Gulf Coast 33946
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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