House holiday rentals in Gasparilla Island

Lake Marlin Villa 2

WELCOME to this affordable, charming and unique villa, all spotless and immaculate, cleaned with passion, love and hospitality, to honor you; The GUEST of HONOR. This 2-bed, 2-bath, 2-car garage and plenty of outdoors, offers you the comfort of feeling home, yet the adventure of your getaway vacation. Overlooking the blue waters of Lake Marlin, away from traffic and noise pollution, yet close to stores, golf clubs and main roads taking you within minutes to Manasota Key and Boca Grande Beaches.

Sunset Beach House

This beautiful beachfront house is located on Little Gasparilla Island with three-bedroom/two-baths. It is tucked away, just off the main drag of this quiet, “off the beaten path” island. Escape your busy life on the mainland and enjoy outdoor living space with amazing 180-degree views of the Gulf of Mexico. Enjoy your private beach path and shared dock, which is perfect for fishing! You can catch your dinner and come back to the house and grill it on deck while watching a breath-taking sunset.

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!

Luxury Retreats at Boca Grande - Grande Canal

Three bedrooms, two bath retreat located a few blocks from town and the white sandy beaches of Boca Grande. Full kitchen with island and family room. A separate workspace lets you work remotely. Enjoy the deck, porch, pool, and dock. Fish and crab off the dock. Bring your boat or charter one. Stroll the barrier islands and marvel at the tropical palms, flowers, and birds. Recharge and restore yourself in nature, in town. Very walkable, only a few blocks downtown to restaurants and shopping.

NEW! Beachfront!3BR Suites Sustainable Home+Dock

NEW LISTING!! 💰No nickel & diming—AirBnb & cleaning fees included! 🚤 Boat-access-only retreat with private dock 🏖️ Steps to pristine beach 🌊 Panoramic water views from every room 🛏️ 3 private queen ensuites 🍽️ Premium kitchen + grill ☀️ Tesla solar + 🚀 Starlink WiFi 🛁 Breathtaking sunset views 🛶 Kayak, SUP & e-bikes included 🌿 Surrounded by protected preserve; only one nearby home 🐬 Incredible wildlife viewing ✨ Perfect for nature lovers, anglers & tranquility seekers

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!

Perfect Beach House Excellent Location

Perfect Beach House, Excellent Location - Quiet Street & Very Short Walk to Beach. This Pilot Street beach house is the perfect getaway for your vacation. Three bedrooms, two full bath with a large great room and extended outdoor living space. Kitchen fully renovated (granite counters, new stainless appliances, bar stool seating). All new mattresses. The premier location in Boca Grande near the beach, walk to town, shop, dine at one of the 14 restaurants with fresh local catch...

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

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!

little Gasparilla Island Beach house-Dog friendly

Escape to Beach Hair Don’t Care on Little Gasparilla Island! This cozy 2BR, 2BA retreat sleeps 5 and is just steps from the bay and 100 yards from a private beach. Enjoy uncrowded beaches, fishing, wildlife, and water sports. Pet-friendly with a fully stocked kitchen, beach gear, boat slip, and golf cart access. Experience the serenity of this car-free island paradise, perfect for relaxing, unwinding, and making memories. Book your escape today!

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.