Family-friendly holiday rentals in Gasparilla Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Gasparilla Island

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Two individuals ride bicycles along a sandy beach at sunset, with vibrant hues of orange and purple in the sky. Gentle waves lap at the shore, and distant figures can be seen walking along the coastline, creating a serene beach atmosphere.

Cottage in Englewood

4.89 out of 5 average rating, 209 reviews

Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath

Unit # 2 Beautiful 2 bedrooms 2 bath cottage, great space to relax with family and friends. With full kitchen/ garage/laundry/outdoor shower. WiFi/Free bikes, kayaks, beach toys. Great Lanai to spend wonderful afternoons. You will love to walk to the beach and enjoy the most breathtaking sunset pictures. cottage is fully furnished beach style for a wonderful vacation feeling. You have not only the beach and the bay to explore, but great restaurants/bars and more just walking distance. Enjoy!

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Guest favourite

Home in Don Pedro Island

4.91 out of 5 average rating, 22 reviews

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.

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Top Guest favourite

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

Home in Captiva

4.91 out of 5 average rating, 142 reviews

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!

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Top Guest favourite

Home in Placida

4.95 out of 5 average rating, 37 reviews

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)

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Top Guest favourite

The outdoor pool area features a screened enclosure, revealing lush greenery in the surrounding landscape. A comfortable seating area with lounge chairs is present. Colorful towels and glasses are arranged on the edge of the pool, with the still water reflecting the evening light.

Home in Rotonda

4.93 out of 5 average rating, 72 reviews

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.

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Top Guest favourite

An aerial view showcases a raised townhome surrounded by palm trees, with the beach and ocean visible in the background. The home's light blue exterior complements the coastal setting, while a spacious deck on the lower level offers an inviting space for relaxation.

Townhouse in Englewood

4.96 out of 5 average rating, 161 reviews

Amazing Sunsets just 50 steps to uncrowded beach

Escape to your dream coastal retreat! This exquisite 2- king bedroom, 2-bathroom home is a paradise, located just steps from the beach. Nestled among swaying palm trees, this haven offers a serene oasis where the calming sounds of the water create a tranquil atmosphere for you and your loved ones. Live among palm trees, with the ocean as your neighbor and the sand as your playground. Natural light floods the modern interior through the large windows creating a warm and inviting atmosphere.

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Guest favourite

Home in Captiva

5.0 out of 5 average rating, 13 reviews

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

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Top Guest favourite

A beach house with a two-story design is surrounded by lush greenery and palm trees. A driveway leads up to the property, which features large windows and a covered porch. A golf cart is parked in the foreground, enhancing the coastal appeal.

Home in Boca Grande

4.96 out of 5 average rating, 79 reviews

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...

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Guest favourite

A serene beach scene showcases smooth, soft sands meeting the gentle waves of a turquoise ocean. A piece of driftwood rests in the foreground, complementing the clear blue sky and tranquil waters that stretch into the horizon.

Home in Captiva

4.94 out of 5 average rating, 156 reviews

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

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Top Guest favourite

Cottage in Don Pedro Island

4.99 out of 5 average rating, 78 reviews

Island Getaway, Beach House, Dock, Pet Friendly

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off Florida’s West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

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Guest favourite

A single-story beachfront home is set amidst lush greenery and palm trees. The exterior features a soft blue hue with multiple windows, each equipped with protective shutters. A sand and gravel driveway leads up to the entrance, contributing to the property's inviting ambiance.

Home in Boca Grande

4.98 out of 5 average rating, 45 reviews

BG Beach House North Unit-Great Price & Location

Boca Grande Beach House - North Unit, is half of a 1-story duplex. It has 2 bedrooms, living/dining rm, a fully stocked kitchen & 1 bathroom with step-in shower. There is a large screened porch across the back and a generous side yard with table & 4 chairs, 2 lounge chairs. We are directly across the street from the beach & tennis courts are down the street. It is a short walk to the Community Center with a playground for kids and to the charming town of Boca Grande..

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Guest favourite

The charming villa is framed by lush palm trees and vibrant greenery, with a private dock visible at the water's edge. A boat is moored nearby, and the sky is bright with scattered clouds, while the three-story structure exhibits a classic coastal design.

Villa in Boca Grande

4.88 out of 5 average rating, 43 reviews

Luxury Retreats at Boca Grande - Boca Bay Watch

Watch the yachts cruise by en route to and from Miller's Dockside, while rocking on your private and serene breeze-filled balcony. Boca Bay Watch sleeps 8 and has 3 bedrooms and 3 bathrooms. This charming villa is a quick walk or golf cart ride downtown Boca Grande for shopping and dining. It is a most idyllic and exclusive community. Very walkable area allows for viewing of local palms and birds and exotic wildlife in addition to local attractions.

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