
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.

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.
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Modern Island Oasis: steps2beach
🏝️Island fun + luxury🥂living = the perfect getaway! 👣 Just steps to the beach & the bay/dock 🦋 High-end fixtures & fittings: -Custom LED lighting modes -Stunning kitchen -Stylish tile floor -Gorgeous granite counter tops -Micromesh screened balcony: 100% bug free 🏠 The most luxurious home on LGI 🏓 Packed with toys+games 🛝THIS is your Paradise Playground 🥇 Guest Favorite: Rated Top 5% 🙋 For those who want to max out on fun, in luxury, style & comfort… 🎯 Look no further: this is the #1
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LUX Villa w/ Private Salt Water Pool, Lanai, Canal
Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!
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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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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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Island Getaway Pool-Ferry-Grocery Delivery Incl.
10-minute passenger ferry ride to this boat-access-only, car-free island Locally Owned & Operated Updated LGI Condo with Magnificent Views 2 private SW facing decks offer a.m Sun, Gulf, Palm & Pool Views. Beautifully furnished with everything to enjoy your Island time Uncrowded shelled beach with Birds, Dolphin and Manatee -Venture out for Prime Fishing & Kayaking SWFlorida has to Offer There are no grocery stores or restaurants on the island, plan to bring everything you’ll need with you
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Last Minute Offers Beach + Golf Cart + Club
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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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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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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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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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!
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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.
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Popular amenities for Gasparilla Island family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Riverfront Retreat • Pool & Spa • 60ft Dock
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Beachhouse w/ Pool&Spa-WALKtoBEACHinLESSthan 1MIN
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Coral Cottage hidden in Palms short walk to Beach
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Gumbo Limbo North Captiva
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Luxury Waterfront Home/Hot Tub/BBQ | 8 Guests
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Vacation Paradise in Rotonda
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Paradise on canal minutes to Ft Myers Beach/Gulf
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Pearl of the Island for 2
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Family- and pet-friendly home rentals

Luxury Canal Villa•Heated Pool•Dock•Arcade•Kayaks
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Island Escape • Quiet Beaches • Great Value
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Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI
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Unit #2 Free bikes/kayaks/walk to beach/2bed/2bath
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Steps to Private beach, Prime Location! Dogs ok!
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Happily Ever After
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Poseiden House on Little Gasparilla Is
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ArtSea Beachfront Remodeled Pool Old Florida
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Family-friendly home rentals with a pool

Coastal Sanctuary - Pool & Privacy
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❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*
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Ibis Cottage | Beachfront Retreat on Manasota Key
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New Home! Heated Pool · Outdoor Bar · 2 Golf Carts
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Turtle Bay - minutes to Boca Grande!
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Island home w/POOL, Private DOCK & BEACH access!
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luxury Brand new villa with pool
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Villa510~3 En-Suites~Gulf Access, Heated spa~pool
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Destinations to explore
- Miami Holiday rentals
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- Siesta Beach
- Captiva Island
- Lido Key Beach
- Turtle Beach
- Caspersen Beach
- Manasota Key Beach
- Crescent Beach
- Englewood Beach
- Lovers Key Beach
- Florida Gulf Coast University
- Myakka River State Park
- Lido Beach
- Stump Pass Beach State Park
- Bowman's Beach
- Blind Pass Beach
- Barefoot beach Bonita Springs,FL
- North Jetty Beach
- Jetblue Park
- Bonita National Golf & Country Club
- Boca Grande Pass
- Tiny House Siesta
- Edison & Ford Winter Estates
- South Jetty Beach
- Yacht Club Public Beach





