Gasparilla Island vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Gasparilla Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gasparilla Island vacation rentals
Gasparilla Island beachfront vacation rentals
Condo in Englewood
4.95 out of 5 average rating, 107 reviewsSunset Beach
Condo in Sanibel
4.88 out of 5 average rating, 234 reviewsRare walkout condo on Sanibel beach-Fully Restored
Condo in Englewood
4.78 out of 5 average rating, 111 reviewsEntire Beachside Condo! Don’t worry Beach Happy!
Condo in Siesta Key
4.96 out of 5 average rating, 296 reviewsWE ARE OPEN—On the Beach; Siesta Key SunBum Studio
Home in Englewood
5 out of 5 average rating, 26 reviewsVacation Condo- Beach Access!
Cottage in Bokeelia
4.99 out of 5 average rating, 121 reviewsRomantic Getaway “Waterside” Dockage~Canal front
Home in North Fort Myers
4.82 out of 5 average rating, 205 reviewsPrivate Cozy Guest House on Water
Serviced apartment in Siesta Key
4.99 out of 5 average rating, 167 reviewsSiesta Key #1 Beach, pickle ball & tennis paradise
Gasparilla Island house rentals
Home in Cape Coral
4.89 out of 5 average rating, 203 reviewsModern Oasis pool paradise
Home in Englewood
4.94 out of 5 average rating, 116 reviewsIsland Home, Casita, Saltwater Heated Pool, Beach
Home in Englewood
4.98 out of 5 average rating, 117 reviewsPRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!
Home in Englewood
4.97 out of 5 average rating, 30 reviews3 miles to beach, hottub & fenced yard for pup
Home in North Port
4.97 out of 5 average rating, 118 reviewsCozy & Beautiful Pool Villa in Sarasota County, Fl
Home in North Port
4.9 out of 5 average rating, 117 reviewsPrivate Small Vacation House
Home in Saint James City
4.98 out of 5 average rating, 181 reviewsRelaxing Waterfront Retreat: 1400 sq ft Home
Home in Cape Coral
4.99 out of 5 average rating, 198 reviewsLUX Villa w/ Private Salt Water Pool, Lanai, Canal
Beachfront house rentals in Gasparilla Island
Home in Placida
5 out of 5 average rating, 31 reviewsCanal home with heated pool, close to everything!
Home in Manasota Key
5 out of 5 average rating, 19 reviewsThe Sand Dollar-WALK to Beach in less than 1 MIN!
Home in Englewood
5 out of 5 average rating, 32 reviewsCape Haze Cottage
Home in Placida
4.95 out of 5 average rating, 40 reviewsCocoHut
Home in Englewood
5 out of 5 average rating, 32 reviews"Lost Loon" Oceanfront Cottage by Roxy Rentals
Home in Englewood
4.88 out of 5 average rating, 8 reviewsSun-Soaked Beach House
Home in Bokeelia
5 out of 5 average rating, 16 reviewsSunset Serenity: Waterfront Oasis
Home in North (Upper) Captiva
5 out of 5 average rating, 10 reviewsSandy Toes Villa - North Captiva - Water Views
Your guide to Gasparilla Island
All About Gasparilla Island
Aquamarine waters, endless stretches of white-sand beaches, and palm-lined walking paths adorn this barrier island in the waters of southwest Florida’s Gulf Coast. Gasparilla Island functioned as a fishing village for much of its history, and today is also a popular wintering destination among a certain celebrity set. Along Gasparilla Island’s waterfront, golf carts zip up and down the coast, and you’ll find bohemian cafes, fresh seafood restaurants, and a shopping complex inside a converted 20th-century train station.
A gateway to Gasparilla Sound and Charlotte Harbor, Gasparilla Island is renowned for its world-class tarpon fishing, easy access to surrounding nature reserves, and a continuous seven-mile stretch of pristine beach. Swimming, kayaking, and hiking through the region’s mangrove forests are some of the region’s more popular activities. Visiting the area’s historic lighthouses and enjoying sunset picnics on the beach are among the many memorable experiences you can enjoy here.
The best time to stay in a vacation rental in Gasparilla Island
Gasparilla Island’s sunny Gulf Coast climate bestows it with pleasant year-round conditions — sunlit days, clear blue skies, and breezy afternoons among the miles of palm-lined beaches. Temperatures vary between the summer and winter months somewhat, but they tend not to drop below uncomfortable levels for swimming or other ocean-bound recreation. Rainfall tends to increase towards the latter half of summer with the arrival of hurricane season, though visitors can still be found in the area during this time. The shoulder season’s warmer temperatures, lack of accompanying rainfall, and myriad events in the surrounding communities make this an excellent time to look for vacation rentals on Gasparilla Island. One of the more prominent events in the region is a large sand sculpting festival that takes place every November in Fort Myers. This 10-day competition welcomes sand sculptors from around the world.
Top things to do in Gasparilla Island
Port Boca Grande Lighthouse & Museum
Beginning operation in 1890, this lighthouse is the oldest structure on Gasparilla Island and the only beacon on Florida’s west coast open to the public. Located in the Gasparilla Island State Park, the lighthouse formerly housed a private residence on its ground level, now transformed into a museum detailing the region’s cultural history, ranging from indigenous cultures that date back more than 12,000 years to the now-famous fishing the area is known for.
Cape Haze Aquatic Preserve
This collection of protected mangrove islands and seagrass ecologies is home to more than 200 species of fish and several species of migratory birds. Bordered by the Gasparilla Sound to the west and Charlotte Harbor to the south, Cape Haze Aquatic Preserve is a popular snorkeling spot. You can also rent a kayak to explore the winding mangrove forests along the waterfront.
Little Gasparilla Island
The smaller cousin of Gasparilla Island, this rural retreat is cut off from the mainland and is only accessible to private boats or water taxis. Along the wide sandy paths, you’ll find golf carts — the only form of motorized transport allowed on the island — cruising up and down the coast amid a picturesque backdrop of pristine beaches.
Destinations to explore
- Sarasota Vacation rentals
- Naples Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Havana Vacation rentals
- Varadero Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes