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, 144 reviewsThe Secret Island Retreat HeatedPool/4b/open water
Jul 13 – 20
Apartment in Englewood
4.92 out of 5 average rating, 125 reviewsShoreview Beach House, Unit A
Oct 1 – 8
Condo in Englewood
4.95 out of 5 average rating, 99 reviewsSunset Beach
Dec 18 – 25
Condo in Englewood
4.94 out of 5 average rating, 116 reviewsGulf Side Condo Englewood Florida
Nov 21 – 28
Home in Englewood
4.96 out of 5 average rating, 104 reviewsWaterfront Cottage by Manasota Key
Sep 12 – 19
Home in Placida
5.0 out of 5 average rating, 52 reviewsLu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI
Apr 17 – 24
Home in Boca Grande
4.95 out of 5 average rating, 58 reviewsPerfect Beach House Excellent Location
Oct 2 – 9
Bungalow in Boca Grande
4.88 out of 5 average rating, 26 reviewsBoca Grande Beach Cottage
Oct 11 – 18
Gasparilla Island house rentals
Home in Englewood
4.98 out of 5 average rating, 108 reviewsPRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!
Apr 9 – 16
Home in Englewood
4.84 out of 5 average rating, 154 reviewsManasota Key Florida House Rental
Jan 1 – 8
Home in Englewood
4.89 out of 5 average rating, 9 reviewsQuaint Surf Cottage on Beach
Dec 5 – 12
Home in Englewood
5.0 out of 5 average rating, 15 reviewsVacation Condo- Beach Access!
Sep 15 – 22
Home in Captiva
5.0 out of 5 average rating, 4 reviewsTurtle Escape: Pool, Beach & Fun!
Sep 18 – 25
Home in Englewood
5.0 out of 5 average rating, 25 reviews"Lost Loon" Oceanfront Cottage by Roxy Rentals
Jan 25 – Feb 1
Home in Placida
5.0 out of 5 average rating, 24 reviewsClose to beaches, canal view, golf, fishing
Sep 23 – 30
Home in Placida
5.0 out of 5 average rating, 7 reviewsJust listed! BRAND NEW Coastal Sol on Palm Island!
Sep 11 – 18
Beach house rentals in Gasparilla Island
Home in Matlacha
4.98 out of 5 average rating, 184 reviewsMatlacha Paradise! NEW Waterfront Home-Free Kayaks
Jul 18 – 25
Home in Captiva
4.97 out of 5 average rating, 101 reviewsSteps To Private Beach Captiva Retreat Golfcart
Nov 20 – 27
Home in Captiva
4.91 out of 5 average rating, 102 reviewsBlue Laguna - Vacation in paradise!
Mar 9 – 16
Home in Port Charlotte
4.94 out of 5 average rating, 105 reviewsRelaxing Little Getaway! Close to everything!
Oct 17 – 24
Home in Englewood
4.99 out of 5 average rating, 102 reviewsParadise on the Bay
Feb 23 – Mar 2
Home in Cape Coral
4.98 out of 5 average rating, 132 reviewsJewel on the River- Magnificent 5 bed/4 1/2 bath
Dec 13 – 20
Home in Captiva
5.0 out of 5 average rating, 6 reviewsBeach Paradise: Oceanfront, Sleeps 10, Pool, Games
Apr 23 – 30
Home in Englewood
5.0 out of 5 average rating, 14 reviewsBeth's Beach Bungalow
Aug 20 – 27
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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