Where to stay around Gasparilla Island?

Our 2019 property listings offer a large selection of 1,225 vacation rentals near Gasparilla Island. From 597 Houses to 308 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Gasparilla Island for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in Gasparilla Island?

There are many lovely places to stay for a holiday trip or just for a weekend in Gasparilla Island. From VRBO travelers, the top most popular destinations to visit are:

  • Sanibel: 5,655 vacation rentals
  • Pelican: 1,409 vacation rentals
  • Florida Gulf Coast: 29,041 vacation rentals
  • Englewood: 2,243 vacation rentals
  • Captiva: 1,354 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in Gasparilla Island! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Gasparilla Island?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Gasparilla Island:

  • Sanibel: 5,655 rentals
  • Englewood: 2,243 rentals
  • Captiva: 1,354 rentals
  • Placida: 975 rentals
  • Punta Gorda: 1,199 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Southern charm and simpler times in Florida's "other" Boca

There's no question that this quaint and quiet barrier island just off Florida's Gulf Coast easily recalls a simpler time. With no roads and limited car access, the island's main town of Boca Grande is similar to the mainland's Boca Raton in name only! This Boca is without traffic lights, chain stores, and highrises. Here, it's easy to settle into the laid back coastal vibe, which means finding the perfect Gasparilla Island vacation rental to call your homebase. If there's anywhere worth experiencing like a local, it's this dreamy little island chock full of Southern charm.

Fun for the whole family, on and offshore

At only three square miles, it's easy to see the entire island by bike or golf cart -- and most do. Gasparilla Island is a year-round haven for fishermen and beach-goers, but those seeking more indoor activities will enjoy its few small museums, or the locally owned shops in the heart of Boca Grande. The island's true highlights, however, are found offshore. Boat charters offer fishing opportunities and dolphin watching, and a variety of watersports, such as kayaking, jet skiing, and stand up paddle boarding, are available around the island.

Culture, history and natural beauty from end to end

While much of the island's charm is found outside, one of its most popular attractions is the Port Boca Lighthouse Museum. In a structure dating back to 1890 and nestled in Gasparilla Island State Park, it explores the island's history from 12,000 BC to now. After, see the natural beauty firsthand -- from the museum's front porch or along the Boca Grande Bike Path. Running the length of the island, the six-mile path follows an old rail bed, and is perfect for self-guided tours or cooling off on one of the readily accessible beaches.

Sun, sand and swimming all year 'round

Thanks to an annual average temperate of 75 degrees, it's likely you can take a dip no matter the season. While the mercury does drop a bit in December and January, calm tropical breezes still might make for perfect beach days. June through September can be fairly rainy, but you can look at this as nature's way of cooling off those humid summer days. The best advice is to pack light, but with an extra layer or two for snuggling up in your Gasparilla Island vacation rental on those cool winter nights or rainy summer evenings.

Stunning natural beauty from coast to coast

There's no question that the island packs a ton of natural beauty into a decidedly small space. Featuring national parks, bike paths, and pristine beaches around every corner, it's not hard for a nature lover to feel immediately at home in a Gasparilla Island vacation rental. With no bridge access to the mainland, travelers and locals alike can bond over the remote beauty and old-school Southern charm that's an essential part of life on this tiny little island in the Gulf.

Explore destinations around Gasparilla Island

5,655 vacation rentals
2,243 vacation rentals
1,354 vacation rentals
975 vacation rentals
Punta Gorda
1,199 vacation rentals
Boca Grande
1,392 vacation rentals
Saint James City
5,384 vacation rentals
North Port
2,369 vacation rentals
Manasota Key
1,928 vacation rentals
2,575 vacation rentals
234 vacation rentals
Rotonda West
1,411 vacation rentals
Pine Island Center
2,348 vacation rentals
South Venice
2,958 vacation rentals
Useppa Island
658 vacation rentals
Warm Mineral Springs
1,232 vacation rentals
Cape Haze
904 vacation rentals
Punta Rassa
5,829 vacation rentals
Lake Suzy
367 vacation rentals
Fort Ogden
368 vacation rentals