Treetop Privacy, Island Breezes & Barefoot Adventures

Tucked high in the tropical canopy along Jolly Roger Trail near the south end of Little Gasparilla Island, this charming island treehouse feels like your own private hideaway in paradise. LGI is one of Florida’s last bridgeless barrier islands, so you’ll leave your car (and your stress) on the mainland and step straight into laid-back island living.

Inside, the home is bright, open, and designed for easy vacation comfort. Spacious bedrooms open directly onto the screened porch, letting those Gulf breezes roll right through the house. The large air-conditioned living area gives everyone plenty of room to relax after long beach days.

The master suite sits privately on its own side of the home and feels like a true island retreat. It features a king bed, en-suite bath with shower, and its own private deck overlooking the backyard treetops. French doors open straight onto the screened porch so you can step outside with your morning coffee or evening glass of wine.

The second bedroom offers two twin beds and also opens to the screened porch through French doors — perfect for kids, friends, or anyone who loves waking up to island air.

The kitchen is fully equipped with stainless appliances, all cookware and dishes you’ll need, plus seating for four at the island — perfect for quick breakfasts before beach time or late-night snack runs after sunset.

The front screened porch stretches across the entire width of the home and nearly doubles your living space. It’s breezy, peaceful, and private — you might see the occasional golf cart cruise by on Jolly Roger Trail, but mostly you’ll just hear palms rustling and birds calling.

The owner includes free kayaks if you want to explore the bay, plus beach towels and beach chairs so you’re always beach-ready. Golf cart rentals may also be available with this property (based on availability).

Out back, a covered porch overlooks the treetops — a perfect quiet spot for sunrise coffee. There’s also a private open sun deck off the master bedroom, ideal for soaking up warm January sunshine or enjoying a quiet afternoon nap in the island air.

What really makes Key2TheSea special is the peace and privacy. Set back from the road on a quiet, rarely traveled path, it’s a true escape. And when you’re ready for sand and surf, the gorgeous Gulf beach is only about a 5–7 minute walk away.

Key2TheSea is perfect for guests who want a quiet island retreat, surrounded by nature, with easy access to Little Gasparilla’s beautiful beaches and world-class fishing.