Family-friendly vacation rentals in Little Gasparilla Island

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Little Gasparilla Island

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

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Top guest favorite

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

4.9 out of 5 average rating, 211 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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Superhost

The beach house stands prominently against a vibrant sunset sky, showcasing its welcoming façade. A sandy path leads through lush landscaping, guiding the eye toward the tranquil waters in the background. The scene radiates an inviting coastal charm, melding structure and nature.

Home in Don Pedro Island

4.93 out of 5 average rating, 44 reviews

#1 House in #1 Location on LGI

🔝6 REASONS WHY CocoHut is the #1 HOUSE in the #1 LOCATION on 🏝️: 1. PANORAMIC VIEWS 🪟Floor-to-ceiling windows across the entire beachfront 2. SCREENED-IN LANAI 🌅Enjoy being outside more -especially for sunset dining 3. 🛏️ 3 MASTERS with MODERN, LUXURIOUS, EN-SUITES: 2 kings, 1 queen + 4th bedroom 4. 🤫 UNSURPASSED PRIVACY, QUIET & SECLUSION 🚫No overlooking neighbors thanks to 2 adjoining vacant lots 5. 😍 PURE BEACH VIEW 🛖Not spoilt by houses in the water 6. WIDEST SECTION OF SAND BEACH

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Top guest favorite

Home in Don Pedro Island

4.92 out of 5 average rating, 24 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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Superhost

Home in Don Pedro Island

4.89 out of 5 average rating, 36 reviews

Zen Oasis Private Island Home 2nd Row on the Beach

Wake up to dolphins, end your days with unforgettable sunsets. This dreamy beachfront escape sits directly on a private, shell-strewn beach where every walk feels like a postcard moment. Unwind to the sound of the waves at the Zen Oasis. Every angle of the home captures the beauty of the beach, sky, and trees. See thousands of stars at night with almost no light pollution. Only a 10-minute water taxi ride to paradise. This is more than a stay—it’s a beachfront experience you’ll never forget.

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Guest favorite

An aerial view of Manasota Key showcases the expansive beach lined with soft sand and crushed shell. The vacation home is highlighted, surrounded by lush greenery and close proximity to the warm Gulf waters, with clear blue skies enhancing the tranquil environment.

Bungalow in Englewood

4.83 out of 5 average rating, 122 reviews

LG Beach Bungalow on Gulf w/Bay Access & deck too!

Welcome to Golden Girl. Our 3 bedroom 2 bath home is totally renovated with all new furniture. A 2nd level observation deck, private hot tub, bunkroom sleeps 6, two bdrms with kings, queen sleeper sofa in LR, laundry, high speed WIFI, all new appliances, smart TV's, so much more! Lanai opens up to semi private beach and a quiet neighborhood of single family homes. There is Bay access too. Kayaks available for rent. There is a separate apartment above not included. The location cannot be beat!

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Top guest favorite

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 favorite

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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Top guest favorite

A vibrant blue exterior of the home is showcased, framed by tall palm trees under a partly cloudy sky. A spacious driveway is visible, providing ample parking space in front of the house, which features a welcoming façade with multiple windows.

Home in Englewood

4.98 out of 5 average rating, 146 reviews

Steps to Private beach, Prime Location! Dogs ok!

Luxury Prime Island Location-Enjoy the best location on the island with our family & pet-friendly home (pets require approval & $200/pet fee). Just steps from our private beach & 1 mile from bars and restaurants, with a free shuttle service to beaches, dining, & nightlife. Relax in comfort w/ soft beds, a spacious couch, and flat-screen smart TVs in every room & fast WiFi. We offer bikes and beach equipment. 1 mile from Manasota Key public beach. Book now for the ultimate island retreat!

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Guest favorite

The beachfront cottage is surrounded by lush foliage, showcasing a two-story structure with a metal roof and large windows. Soft light spills from the interior, highlighting a welcoming atmosphere. A wooden walkway leads to the entrance, inviting guests to explore the natural surroundings.

Home in Don Pedro Island

4.9 out of 5 average rating, 30 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

Welcome to the most secluded spot on Little Gasparilla Island! Our Beach Cottage property is on the beach with all-natural surroundings: a state park, a mangrove lagoon, and the Gulf of Mexico. It boasts front views of the water and gorgeous island sunsets year-round. You'll have boat space on our private dock and amenities including kayaks, paddle boards, an outdoor bayside dining area, coffee bar with complimentary coffee, private grilling area, fire pit, and much more!

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Top guest favorite

Home in Don Pedro Island

5.0 out of 5 average rating, 31 reviews

Island Getaway, Beach House, Water View, Dock

Embark on your next adventure at this unique and serene retreat that can only be reached by boat. LGI is a barrier island off the West Coast of Florida in the Gulf of Mexico between Sarasota and Ft Myers. Arrive at the island using your private boat or by boarding the water taxi, and be at our dock in just 10 minutes. There are no cars, shops, or restaurants on the island, the 7-mile beach is private and uncrowded. You can explore LGI by renting a golf cart or by walking

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Guest favorite

A serene beach scene showcases gentle waves lapping at a sandy shore. Lush greenery is visible along the coastline, with a residential property nestled among the trees. The clear blue sky complements the tranquil waters, creating a peaceful environment.

Home in Englewood

4.96 out of 5 average rating, 101 reviews

Welcome to one of Florida’s best hidden gems! A beautiful beach home with private beach access, a butterfly garden and a game room. Enjoy a dream stay by the sea in one of most beautiful Keys in Florida.

Relax with the whole family at this peaceful place to stay.Our home offers you at-home comfort for up to 8 people. Large spacious bedrooms, a fully equipped kitchen with breakfast bar, and multiple patios and balconies to enjoy. For winding down after a long day, spend some quality family time in our game room. Your little ones can pretend to grill up some burgers while mom and dad play a round of ping pong or get the whole family together for some board games!

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Top guest favorite

A spacious living area is filled with natural light, featuring a large sectional couch adorned with orange accent pillows. A modern kitchen is visible in the background, equipped with stainless steel appliances and a dining area with wooden chairs and a table. Soft lighting illuminates the space.

Home in Don Pedro Island

5.0 out of 5 average rating, 36 reviews

Island Escape • Deep Water Dock • Quiet Beaches

Escape to Coastal Sol, a newly built 3-bedroom, 2.5-bath retreat on peaceful Don Pedro–Knight–Palm Island. A short 5-minute car ferry brings you to this bridgeless barrier island, where seven miles of uncrowded Gulf beaches, warm coastal breezes and spectacular sunsets await. Enjoy nearby deep-water dock access for boating and fishing, explore the island by golf cart or bike, and experience the laid-back Old Florida charm that makes Palm Island so special.

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