Gasparilla Island vacation rentals

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Popular amenities for Gasparilla Island vacation rentals

Other great vacation rentals in Gasparilla Island

Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 142 reviews

The Secret Island Retreat HeatedPool/4b/open water

Sep 20 – 27

G$62,688 GYD per night
Guest favorite

Apartment in Englewood

4.92 out of 5 average rating, 124 reviews

Shoreview Beach House, Unit A

Oct 24 – 31

G$40,552 GYD per night
Guest favorite

Villa in Englewood

4.92 out of 5 average rating, 110 reviews

Magnificent Waterfront! Kayaks-Pool-Beach! gs

Oct 20 – 27

G$32,651 GYD per night
Guest favorite

Apartment in Sarasota

4.9 out of 5 average rating, 241 reviews

VILLA 3 · Pool view. Walk to beach. Daily rentals

Jan 9 – 16

G$19,239 GYD per night
Guest favorite

Condo in Englewood

4.94 out of 5 average rating, 116 reviews

Gulf Side Condo Englewood Florida

Dec 23 – 30

G$45,746 GYD per night
Guest favorite

Home in Englewood

4.84 out of 5 average rating, 153 reviews

Manasota Key Florida House Rental

Jan 1 – 8

G$32,313 GYD per night
Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Aug 11 – 18

G$24,907 GYD per night
Guest favorite

Home in Englewood

4.98 out of 5 average rating, 107 reviews

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Apr 19 – 26

G$99,297 GYD per night

Gasparilla Island house rentals

Beach house rentals in Gasparilla Island

Guest favorite

Home in Saint James City

4.98 out of 5 average rating, 174 reviews

Relaxing Waterfront Retreat: 1400 sq ft Home

May 11 – 18

G$29,956 GYD per night
Guest favorite

Home in Captiva

4.91 out of 5 average rating, 102 reviews

Blue Laguna - Vacation in paradise!

Sep 8 – 15

G$116,150 GYD per night
Guest favorite

Home in Matlacha

4.98 out of 5 average rating, 184 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

Jun 30 – Jul 7

G$38,598 GYD per night
Guest favorite

Home in Port Charlotte

4.94 out of 5 average rating, 103 reviews

Relaxing Little Getaway! Close to everything!

Oct 19 – 26

G$23,438 GYD per night
Guest favorite

Home in Cape Coral

4.98 out of 5 average rating, 132 reviews

Jewel on the River- Magnificent 5 bed/4 1/2 bath

Nov 28 – Dec 5

G$239,004 GYD per night
Guest favorite

Home in Englewood

4.99 out of 5 average rating, 102 reviews

Paradise on the Bay

Feb 19 – 26

G$87,727 GYD per night
Superhost

Home in Fort Myers

4.88 out of 5 average rating, 192 reviews

The Beachy Retreat

Aug 8 – 15

G$19,376 GYD per night
Guest favorite

Home in Placida

5.0 out of 5 average rating, 5 reviews

Serendipity bohemian cottage, water view

Oct 19 – 26

G$76,022 GYD per night

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