Updated 1/18/2022 Most of the islands in this list you probably haven’t heard of. They aren’t very well known or popular vacation locations. This is mainly because the thought of planning a trip to an island that is only accessible by boat can be a daunting task. There’s a reason that so many celebrities have houses on islands like North Captiva. The tranquility of these islands is unparalleled in the United States. The fact that you are literally and figuratively “detached” from the rest of the busy world provides a level of relaxation that you can’t find anywhere else. If you are willing to plan a trip a little bit outside your comfort zone, these islands will not disappoint.
DON PEDRO ISLAND
Don Pedro Island is a 7 mile long barrier island in Southwest Florida, off the coast of Port Charlotte/Punta Gorda. This island has one of the most pristine beaches in Florida. This island is one of the most accessible and easy to get to on our list. You can simply drive your car onto the ferry located on the mainland (you can see the ferry company’s site here http://palmislandtransit.com/), then you are free to drive around the island by car to your vacation rental or restaurant.
There are many houses for rent through VRBO on Don Pedro, and you can usually score at great deal most times of the year. Since most people don’t know about this island, it seems to run cheaper than the areas around it like Boca Grande. This would make a great first island vacation destination. Punta Gorda Airport is about a half hour away, but you could also fly into Sarasota or Fort Myers. Allegiant Air sometimes has extremely cheap flights into Punta Gorda. Available House Rentals VRBO Don Pedro
LITTLE GASPARILLA ISLAND
Little Gasparilla Island is very close to Don Pedro. In fact, its attached to it. It is believed that a long time ago water separated the two islands, but storms filled in the passes and they are now connected. Although they are connected, Don Pedro State park lies directly in between the two. This makes it extremely difficult to get from one to the other, so we will consider them separate. Little Gasparilla does not have any restaurants on the island so you will need to bring in groceries. There are actually services that will deliver you groceries by boat, and this is one of the most convenient ways to get your groceries to the island.
Most of the beach houses on Little Gasparilla are stilt houses like the picture above, and you can’t get any closer to the water. House rentals on Little Gasparilla are generally even cheaper than Don Pedro. You can check out the available rentals here: Available House Rentals VRBO Little Gasparilla Island
NORTH CAPTIVA ISLAND
North Captiva Island is the gem of Southwest Florida. Celebrities like Tom Hanks and Shaun Connery own homes here and frequently roam the island. North Captiva is accessible by ferry from the Pine Island Marina. You can check the ferry schedule here: https://www.northcaptiva.com/index.php/ferry-schedule Fort Myers International Airport (RSW) is the closest airport, although Punta Gorda is just 30 miles away. Either are great choices for getting here by plane. The ferry company will also pick up your groceries and have them ready for you.
There are 4 restaurants on the island, you can check the Tripadvisor Reviews of them here: North Captiva Restaurant Reviews-TripAdvisor My favorite is probably Mango’s, and I love the beach bar there. One of the most fun things about North Captiva is the whole island is filled with golf cart paths. Most house rentals come with at least one golf cart and they are used in place of cars on the island. There are ultra luxury homes you can rent here to simple beach cottages. There really is something for everyone here, and it is my top recommendation for anyone looking to take a Florida island vacation.
Since the ferry service started offering the service to pick up your groceries, vacationing on North Captiva is easy. All you have to do is simply show up at the ferry marina, everything else is taken care of. If you want to save a little money, there are excellent rental options a short walk off the beach (not quite beachfront). Here is the VRBO page for North Captiva, you can type in your dates and number of guests and it will show you whats available, Available House Rentals VRBO North Captiva
Cayo Costa is a pretty large island, with over 9 miles of pristine beach. Even though it is large by Florida Gulf Coast island standards, there are only 2 dozen homes on the island. As of posting there are only 3 available to rent, and it’s pretty tough to find availability at any of those 3. If you are up for an adventure that you will never forget, here’s a link to check for availability: Cayo Costa Rental Availability- Vacation Rentals by Owner
If you found this article interesting be sure to check out our brand new List of the Top 5 Hidden Gem Beachfront Florida Cottages here: https://frequentislander.com/5-best-hidden-gem-beachfront-cottages-on-the-florida-coast/