Gasparilla Island vacation rentals
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Top-rated vacation rentals in Gasparilla Island
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Other great vacation rentals in Gasparilla Island
Home in Matlacha
5.0 out of 5 average rating, 142 reviewsThe Secret Island Retreat HeatedPool/4b/open water
Sep 20 – 27
Apartment in Englewood
4.92 out of 5 average rating, 124 reviewsShoreview Beach House, Unit A
Oct 24 – 31
Villa in Englewood
4.92 out of 5 average rating, 110 reviewsMagnificent Waterfront! Kayaks-Pool-Beach! gs
Oct 20 – 27
Apartment in Sarasota
4.9 out of 5 average rating, 241 reviewsVILLA 3 · Pool view. Walk to beach. Daily rentals
Jan 9 – 16
Condo in Englewood
4.94 out of 5 average rating, 116 reviewsGulf Side Condo Englewood Florida
Dec 23 – 30
Home in Englewood
4.84 out of 5 average rating, 153 reviewsManasota Key Florida House Rental
Jan 1 – 8
Cottage in Nokomis
4.98 out of 5 average rating, 123 reviewsStaycation Sanctuary - 100% Smoke-Free Property
Aug 11 – 18
Home in Englewood
4.98 out of 5 average rating, 107 reviewsPRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!
Apr 19 – 26
Gasparilla Island house rentals
Home in Punta Gorda
4.96 out of 5 average rating, 130 reviewsPunta Gorda Isles Gem with Saltwater Spool
Sep 28 – Oct 5
Home in Englewood
4.96 out of 5 average rating, 102 reviewsWaterfront Cottage by Manasota Key
Sep 12 – 19
Home in Cape Coral
4.83 out of 5 average rating, 167 reviewsAmazing Modern Home with Pool and Hot Tub!
Oct 22 – 29
Home in Englewood
5.0 out of 5 average rating, 25 reviews"Lost Loon" Oceanfront Cottage by Roxy Rentals
Sep 25 – Oct 2
Home in Englewood
5.0 out of 5 average rating, 15 reviewsVacation Condo- Beach Access!
Aug 16 – 23
Home in Englewood
5.0 out of 5 average rating, 25 reviewsClean & Comfy Beach Cottage super-close to Gulf!
Nov 9 – 16
Home in Englewood
5.0 out of 5 average rating, 4 reviewsThe Coconut Haven
Jun 25 – Jul 2
Home in Rotonda West
4.89 out of 5 average rating, 9 reviewsParadise Pool Oasis Vacation Home in Rotonda
Sep 4 – 11
Beach house rentals in Gasparilla Island
Home in Saint James City
4.98 out of 5 average rating, 174 reviewsRelaxing Waterfront Retreat: 1400 sq ft Home
May 11 – 18
Home in Captiva
4.91 out of 5 average rating, 102 reviewsBlue Laguna - Vacation in paradise!
Sep 8 – 15
Home in Matlacha
4.98 out of 5 average rating, 184 reviewsMatlacha Paradise! NEW Waterfront Home-Free Kayaks
Jun 30 – Jul 7
Home in Port Charlotte
4.94 out of 5 average rating, 103 reviewsRelaxing Little Getaway! Close to everything!
Oct 19 – 26
Home in Cape Coral
4.98 out of 5 average rating, 132 reviewsJewel on the River- Magnificent 5 bed/4 1/2 bath
Nov 28 – Dec 5
Home in Englewood
4.99 out of 5 average rating, 102 reviewsParadise on the Bay
Feb 19 – 26
Home in Fort Myers
4.88 out of 5 average rating, 192 reviewsThe Beachy Retreat
Aug 8 – 15
Home in Placida
5.0 out of 5 average rating, 5 reviewsSerendipity bohemian cottage, water view
Oct 19 – 26
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.
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