

FALL in Love with Little Gasparilla Island
The best kept secret is the fall months on Little Gasparilla Island. The weather is mild, but warm, most mainland folks have dug into the fall schedules of school and work so there are fewer visitors, making it a great time to get away.
Think about taking a long weekend and bringing your calendars and wish lists and setting your personal priorities and goals for the upcoming year in a serene retreat.
Its a great place and time to restart that walking program… where better than to get your “steps” walking the beach at sunrise or sunset. There are amazing houses/condo’s to choose from. Stay on the beach and enjoy sunsets. Pick a Bay House to watch the sunrise from an upper deck. Pick an interior house that is still only yards to the beach and lets you enjoy all the island offers for a lower price.
Guests are drawn to the island's pristine beaches, crystal-clear waters, and abundant sunshine. Whether relaxing on the sandy shores, fishing in the Gulf waters, or exploring the natural beauty of the island, visitors can unwind and rejuvenate in this idyllic setting. With comfortable accommodations and a laid-back atmosphere, Little Gasparilla Island offers the perfect escape for fall travelers looking to relax and recharge.
Check out our New Listings!
Anchor’s Landing
Blue Pearl
Shine Bay
Oyster Pearl
Turtles Nest
H2 Oasis!
Happy Mermaid
Escape to Paradise - Your Perfect Island Getaway!
Welcome to Little Gasparilla Island. The island shows the resilience of nature and the island residents in the best ways. For those that have been here for many years, the island has a new, more open look with less foliage but white sand and open views. Although there were houses lost to Hurricanes Ian, Helene and Milton, many property owners are rebuilding which is exciting and we look to have several new “old” house back on line over the next 12 months.
LGI is the perfect spot to host small interest groups. Think about hosting your writers retreat, wellness weekend, quilting workshop on LGI. Housing options for shared accommodations or single occupancy for both house and condo’s. We have exciting plans for the fall when its quiet but some of the best weather… not so hot, water is still warm, and no crowds, so stay tuned….
LGI is a great place to bring your friends and enjoy the island together but have some private time. Think “cruise ship vacation on an amazing barrier island”. Ask about houses close together to create your neighborhood on the island for your stay! We have exciting options for multiple house rentals that are located in the same area so you might have one family in a beach house, another in an interior house on the same lane or close by and one on the bay and enjoy getting together easily for daily sunsets, cocktails on a deck, game night or other family fun. Let Terry assist you in planning a great group vacation!
Outdoor Adventures: Embrace the great outdoors with activities like kayaking, paddle boarding, and fishing. The island's tranquil waters and lush surroundings provide the ideal backdrop for exploring nature and staying active. Ask us about local guides and services.
Charming Accommodations: Our collection of vacation rental homes offers a range of cozy, comfortable accommodations to suit your needs. Whether you're seeking a romantic getaway or a family vacation, we have the perfect home for you. We have available houses on the beach or canal: Mermaid House, Seadated, Aldens Retreat, Sand Dollar, Oceanfront Serenity, The Island, Sunny Daze, Coconut Hideaway, Fish On!, and Surf’s Up. Houses on the North End with short walks to beach or Bay: Beach Buzz, Jewel of the Sea, Living Well, Seahorse Cottage, Pelican’s Roost and White Pelican. We have a great selection of bayfront homes with their own private dock for the ultimate convenience: Blue Pearl, Poseidon’s Dream, Oyster Pearl and Shine Bay. And great houses on the south end of the island, also with short walks to the beach: Key2TheSea, Almost Heaven, Lost Key, Pelican Place. Check out these homes and find the best fit for your getaway!
Book Directly and Avoid Booking Fees: Our on Island Guest Services makes booking with Little Gasparilla Vacation Rentals a special experience. We are here to help when the unexpected happens. Say Hi! when you see us around the island! We are excited to be able to share our little piece of paradise with you, your family and friends.
Little Gasparilla Vacation Rentals Team
Terry, Pede and Eileen
Leave your car and your cares at the marina because our homes are only accessible by boat. Hop on the water taxi or bring your own boat to escape to paradise on Little Gasparilla Island!
Little Gasparilla Vacation Rentals is the premier vacation home rental agency on Little Gasparilla Island (LGI). With over 40 homes to choose from, ranging from spacious beachfront homes to cozy inland cottages, we have something for everyone.
We offer homes to accommodate from 2-10 people. OUR EXCLUSIVE ISLAND services include an on-islanD Guest Services Manager, trash removal, and a new optional grocery shopping and delivery service!
If you’re considering a vacation ON LGI, This is THE perfect place to start planning your ISLAND GETAWAY!
WHY LITTLE GASPARILLA ISLAND?
Discover old Florida on this bridgeless barrier island on the Gulf of Mexico in Southwest Florida.
WHY LITTLE GASPARILLA VACATION RENTALS?
Learn about our family owned and operated business with 20+ years of experience renting exclusively on Little Gasparilla.




