Family-friendly holiday rentals in Gasparilla Island

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.

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

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!

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!

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.

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

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!

Ground-Floor 2BR · Private Patio · Steps to Beach

The only ground-floor 2BR flat at Grande Flats — no stairs, a private outdoor patio, and a private entrance. Ideal for families, guests with limited mobility, or anyone who wants everything on one level. Full kitchen, dishwasher, king bedroom, twin second room, washer/dryer. Beach is 120 steps. The Temp is across the street. Hudson's Market down the block. 10% off golf cart and bike rentals through Gasparilla Adventures — park your car on arrival and don't move it again.

Island Getaway•Beach House•Water View•Dock•Pets

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

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!

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.

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!