Vacation Rentals

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Welcome to Docktails, a secluded waterfront retreat on the peaceful shores of Little Gasparilla Island, where island time begins the moment you arrive. Accessible only by boat, this bridgeless barrier island offers the perfect place to disconnect, slow down, and experience Old Florida at its best. Start each morning with coffee on the screened porch as the bay comes to life, then step onto your private dock to fish, launch a kayak, head out boating, or watch dolphins and manatees pass by.

Inside, the bright and open main home makes it easy to relax together after a day on the water. The fully equipped kitchen, dining area, and comfortable living space provide everything needed for a carefree stay. The primary bedroom features a king bed, while the guest bedroom includes a queen bed and twin bunk beds, making the home well suited for families or groups. Just outside, a detached bungalow offers additional privacy with a queen bed and its own full bathroom. To make island adventures effortless, the property also includes Starlink WiFi, DIRECTV, five kayaks, two paddleboards, a canoe, a surfboard, beach chairs, wagons, and plenty of towels.

When you are ready to unwind, rinse off in the outdoor shower, cast a line from the dock, and enjoy a drink as the sky turns shades of pink and gold. With no cars, crowds, or everyday distractions, Little Gasparilla Island invites you to spend your days exploring sandy paths, collecting shells along the Gulf, and taking in unforgettable sunsets. At Docktails, every moment is an opportunity to relax, recharge, and settle into true island living.

Pets are welcome with owner approval, and a nonrefundable fee applies to each pet. Breed and size restrictions may apply. A refundable security deposit of $500 is required. Additional charges include 12 percent tax, cleaning and reservation fees, and a 3 percent credit card processing fee, which is waived for check payments. Smoking is not permitted. Book directly with Tarpon Real Estate to avoid extra booking fees and enjoy more beach days.

Whether your stay is for a week or a lifetime, Docktails makes every day feel like island time.

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