Holiday rentals with a pool in Gasparilla Island

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

Vacation Paradise in Rotonda

This brand-new home with 3 bedrooms and 3 bathrooms is truly designed for comfort and relaxation. The spacious living room, huge kitchen, and big dining room are an open-layout living area. Our outdoor covered grilling area has outdoor furniture a hot tub, and a heated pool. Walking distance to Long Marsh Golf Club, a short drive to 3 more Gulf Clubs. A Playground for the kids and exercise paths are all here. Amazing 7 beaches to choose to visit with very good restaurants close to the area.

Seaside Boca (Pool + Sauna + Mini Golf + Spa)

As seen on TV fun for the whole family at this new Airbnb. With its Key West vibes you’ll be sure to have a great time here! Boca Grande is just minutes away, Publix and shopping center are a short bike ride and boats are welcome as the marina is right next door. House is located in the tranquil area of Cape Haze close to Golf courses where you can stroll or bike to you hearts content. We just added a Game Room, a Pool with jacuzzi, Sauna, plus a multi court and Mini Golf (pics jus refreshed)

3BR Resort Home · Pool, Gym + Beach Club Access

We beat Milton and are ready to host you. The Village Houses in the Boca Grande Club possess a distinct charm that sets them apart. The village houses offer an intimate connection to nature. Our homes is surrounded by lush tropical foliage, providing a serene backdrop of swaying palms and vibrant flowers. Our guests enjoy access to a range of exclusive amenities. Whether lounging by the pool, or indulging in gourmet dining, out home provides a wealth of experiences for our guests.

Turtle Bay - minutes to Boca Grande!

Welcome to Turtle Bay Haven – Your Dream Escape on the Gulf Coast! Stay in your own private natural oasis, surrounded by lush greenery and the vibrant tropics of Florida wildlife. - Grocery Stores: just 5-10 min away - Dining Options: A variety of local restaurants are just min away. - Boca Grande: 11 mi (20 min) away, known for stunning beaches. - Manasota Key Beaches : 10 mi (20 min) - Activities: Kayaking, paddleboarding, fishing, hiking, biking, and over 20 golf courses await!

Beach Getaway + Golf Cart & Club Access

BOOKING FALL 2026 HOST PAYS AIRBNB FEE Golf Cart and Club amenities Included North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and proximity/ steps to the beach

Lux Home on Gulf w/Private POOL & 50ft Dock

Rest your feet & your soul as you getaway from it all! This luxurious little piece of paradise is tucked away on a quiet Gulf Coast waterway. 10min from Englewood Beach and 5 min from stores. Tie your boat up in the back yard to the private 50 ft dock. Spend your days fishing, catching sunsets or in the pool every evening! Easy access to Don Pedro Island, local sandbars, inlet and several restaurants, all at your fingertips! Pack your bags, kick back- paradise is waiting!

Island Home & Casita, Pool, Golf Cart, Beach

Complimentary golf cart INCLUDED. With a short stroll to warm sand and crystal waters of Englewood Beach. With all the the modern comforts in place all you have to do is relax on your short stay or extended visit. Updated 2/2 main house and 1/1 Casita with a private entrance. Walk right out the front door to the new expansive pool patio featuring a saltwater heated pool, outdoor kitchen and plenty of furniture for spending time soaking in the warm Florida sun!

Manasota Key

Direct Ocean Front Unit. Imagine having a glass of wine at sunset overlooking world class views of the Gulf of Mexico. Steps to the beach and unsurpassed views. Excellent restaurants and Tiki Bars within walking distance. This unit is a 1 bedroom 1 bath spacious unit that can comfortably sleep 4. It includes a King bed & Full size sleeper sofa. It also has a beautiful kitchen with granite countertops and tile floors throughout. No Pets.

Paradise on the Bay

Waterfront pool home just a short drive to Boca Grande with all the amenities that you would expect. Enjoy spectacular sunsets over Lemon Bay. With more than 250 ft of seawall for deepwater dockage, this home can accomodate even the largest boats. Fantastic fishing from your front yard! Three bedrooms and two baths make this the perfect vacation destination for family and friends. 3 Kayaks and a canoe are available for your enjoyment.

ArtSea Beachfront Remodeled Pool Old Florida

Welcome to ArtSea -- a beautifully remodeled beachfront condo on Gasparilla Island's Gulf shore. where Old Florida lives on in the best possible way. Step outside your door and you're on the sand: a wide shell-strewn beach where the Gulf of America stretches out in front of you and the sky ignites with color every evening at sunset. Tis is Boca Grande--unhurried, authentic, and unlike anything else on Florida's Gulf Coast.

Waterfront Villa Shellflower with private pool

Villa Shellflower is located in Rotonda West on a large and quiet property. Right next to the property is the Rontonda River, a wide freshwater canal. The 1564-square-foot house has been furnished with great attention to detail. The large saltwater pool, the southwest-facing sun deck, as well as the cozy dining area provide the perfect holiday feeling. The next dream beach is only 20 minutes away by car.