Little Gasparilla Vacation Rentals                                                                             
Your source for the most beautiful vacation rentals on Little Gasparilla Island!


Bud and Laurie Gaines    • LLC         

Terry Simms, On-Island Guest Services

Louisa Mahoney, Booking Manager                                                                                                              






About Us LLC is the most trusted vacation rental resource on Little Gasparilla Island. 

We understand that choosing your family vacation spot is an emotional issue and you want to make sure your vacation home is perfect for your needs.

We will communicate with you throughout the decision-making process so you can make an informed decision.

We work hard to build lasting relationships with each and every guest and we are proud to say that many of our guests have returned year after year!

Most people fall in love with the island after just one visit, and return every year.  Others become so captivated that they have purchased their own little piece of paradise!  Little Gasparilla Island is a mystical island and we never tire of sharing it with friends and family!

Laurie and Buddy Gaines

Why Choose Us?

At LLC, we are backed by over 20 years of experience in the vacation rental business, and we work hard to find you the perfect vacation spot.

We have lived on the island ourselves for over 30 years and are very familiar with all aspects of island living.  We began by renting our own home while we traveled in Europe and did antique shows in the Midwest and New England.  Our goal was to make our guests feel like part of the family and to offer them a well-stocked vacation home that felt like their own beach house. We wanted to avoid the sterile, cookie-cutter ambiance that many vacation rentals offer.  And we wanted to share the unique charms of Little Gasparilla Island and allow others to experience it and learn to love it as we did.

Then, a few neighbors asked us to help them rent their beach homes. Now, we offer a variety of vacation rentals for a select few homes that have been carefully chosen for their quality, their location, their amenities and their value.  We are a small family business and we love to share Little Gasparilla Island with other families.

Louisa Mahoney, our Booking Manager (below) will help you with every aspect of your booking.  She also sends out contracts and keeps our calendars updated.  You can contact her any time you need to change any aspect of your reservation, need a copy of your contract, have a question about your dock number or house address or have questions about your reservation.

Terry Simms is our Guest Services Manager.  She lives on-island and will be available once you arrive to help you with your rental.  Whether you need more toilet paper, forgot to buy ketchup,  need help finding something in the house or just have general questions about how things work on the island.  You can also call her if there are maintenance issues and she can dispatch one of our maintenance crew.  Just keep in mind that everything takes longer to fix on the island!

Special services available for our guests:

• On-island Guest Services Manager...our on-island Guest Services Manager is available to help you with whatever vacation needs might arise...whether you need additional paper towels, help with your DirecTV or additional beach towels.   She can often provide food items or condiments, help with medicinal items or other things that you might have forgotten.

• Private Chef.....we offer you the services of not one but TWO private chefs who can cook a fabulous gourmet meal for a special it a romantic anniversary, a special birthday or a family reunion.  (Because of our island location, they do need at least 48 hours notice for shopping and prep.  See what a recent mother-of-the-bride had to say about our private chefs:

"We've just returned from a wonderful stay on LGI. Having never been there, we did not know what to expect. Talk about southern hospitality! My daughter got married while we were all down there-they honeymooned in the darling Round House. Before the sunset wedding, an amazing group of private island chefs-Terry, Pede, and Austin- prepared a wedding feast for our party of 14 people! From the fresh appetizers to the AMAZING key lime pie dessert (also chocolate cake that was to-die-for), our surf and turf dinner was delicious and we savored every bite. Terry, Pede, and Austin took such good care of us and made sure that everyone was well taken care of and beyond satisfied with their meal -- and we all were! Thank you for a special and memorable dining experience!"
Jenny and Tom Endicott

(Menu planning for a large group will require reservations in advance of your arrival.)

• Island Concierge....our island Concierge will meet you at the dock with his golf cart and help transport luggage and groceries to the house for you. There is no charge for this service. He is also available to help take you back to the dock upon departure.

• Grocery Delivery and Shopping Service.....we now offer both a pre-stocking service which will have your groceries waiting in your home when you check in OR you can place an order mid-week for additional groceries or things you might have forgotten.  We can also arrange to purchase fishing poles and bait for you if you are unable to bring poles with you or do not wish to make a trip back to the mainland to pick up bait.

• Trash Removal (Saturday pick-up only)....we always hated having to haul our trash off the island when we left so we now have made arrangements to remove trash on Satuday mornings for our guests checking out on Saturdays.  Unfortunately, at this time we only offer trash pickups on Saturday.