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Gasparilla Island vacation rentals

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Top-rated vacation rentals in Gasparilla Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire rental unit
  2. Boca Grande
Historic Boca Grande-2 Bedroom Flat: #5 Special Rt

A great 2 bedroom one bath flat in the heart of historic Boca Grande on the gorgeous Gasparilla Island. Located across the street from The Temp Restaurant, down the block from Hudson's Market and around the corner from Sister's Pizza. Going to the beach, no worries, it is just down the road. Rent our place through Airbnb and receive a 10% discount on golf cart and bike rentals. You’ll love my place because of the location, the people, and the neighborhood.

ﺩ.ﺇ915 per night
SUPERHOST
  1. Entire loft
  2. Boca Grande
The Loft on Park Ave--Boca Grande FL

A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

ﺩ.ﺇ1,334 per night
  1. Entire condo
  2. Placida
Boca Grande North - 2 bedroom water front condo with deep water boat dock

Watch the dolphins swim by in this waterfront unit located at Boca Grande North

ﺩ.ﺇ1,084 per night

Vacation rentals for every style

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Gasparilla Island beach vacation rentals

SUPERHOST
  1. Entire condo
  2. Placida
Beachfront Island Isolation Pool/Ferry Service Inc
ﺩ.ﺇ721 per night
  1. Entire townhouse
  2. Boca Grande
Gulf Dunes Seaside Villa 2
ﺩ.ﺇ1,906 per night
SUPERHOST
  1. Entire cottage
  2. Placida
BELLISSIMA BY THE BEACH Secluded Beachfront Home
ﺩ.ﺇ1,488 per night
SUPERHOST
  1. Entire home
  2. Placida
3/2 LGI Gulf Gulf Front w/Dock
ﺩ.ﺇ1,566 per night
  1. Entire cabin
  2. Placida
LunaSea, WATERFRONT cabin. Gilligan's Island !!
ﺩ.ﺇ931 per night
  1. Entire home
  2. Little Gasparilla Island
Little Gasparilla Island Home w/ Scenic Bay View!
ﺩ.ﺇ562 per night
  1. Entire home
  2. Placida
The Round House: Beachfront island cottage!
ﺩ.ﺇ1,440 per night
  1. Entire home
  2. Placida
Pura Vida: Beachfront on Little Gasparilla Island
ﺩ.ﺇ1,561 per night
SUPERHOST
  1. Entire home
  2. Placida
CocoHut~Tub
ﺩ.ﺇ1,282 per night
  1. Entire bungalow
  2. Placida
Knee Deep Beach House on Little Gasparilla Island
ﺩ.ﺇ1,700 per night
SUPERHOST
  1. Entire condo
  2. Placida
LGI HIDEAWAY! includes 6 pass golf cart/ 2 kayaks!
ﺩ.ﺇ880 per night
  1. Entire home
  2. Placida
Gulf Beachside luxury 3BR retreat 360* island view
ﺩ.ﺇ2,020 per night

Gasparilla Island house rentals

SUPERHOST
  1. Entire home
  2. Boca Grande
Comfortable Canal-side Retreat on Boca Grande
ﺩ.ﺇ2,296 per night
  1. Entire home
  2. Placida
Coconut Paradise
ﺩ.ﺇ1,439 per night
  1. Entire home
  2. Boca Grande
Perfect Beach House Excellent Location
ﺩ.ﺇ2,016 per night
  1. Entire home
  2. Boca Grande
The Beachfront Sanctuary on Shore Lane
ﺩ.ﺇ6,112 per night
SUPERHOST
  1. Entire home
  2. Boca Grande
BG Beach House North Unit - Great Price & Location
ﺩ.ﺇ1,047 per night
  1. Entire home
  2. Boca Grande
Sunsets at Sundown Colony ~ beachfront 2/2.5 condo with community pool
ﺩ.ﺇ2,321 per night
  1. Entire home
  2. Placida
Tropical Paradise 0n Little Gasparilla Island
ﺩ.ﺇ551 per night
  1. Entire home
  2. Boca Grande
Boca Grande All-Inclusive Island Estate
ﺩ.ﺇ6,795 per night
  1. Entire home
  2. Placida
Little Gasparilla Island...Secluded Beach Getaway
ﺩ.ﺇ965 per night
SUPERHOST
  1. Entire home
  2. Boca Grande
BG Beach House South Unit - Great Price & Location
ﺩ.ﺇ1,047 per night
  1. Entire home
  2. Placida
Camp GoodNow: Beachfront on a tropical island!
ﺩ.ﺇ1,745 per night
  1. Entire home
  2. Placida
Panasea: Beachfront on Little Gasparilla Island!
ﺩ.ﺇ1,501 per night

Beach house rentals in Gasparilla Island

SUPERHOST
  1. Entire home
  2. Placida
Little Gasparilla Island Beachfront Oasis
ﺩ.ﺇ1,837 per night
  1. Entire home
  2. Placida
Sea Star: Beachfront on Little Gasparilla Island!
ﺩ.ﺇ1,377 per night
  1. Entire home
  2. Placida
Mermaid Beachhouse Beachfront on a tropical island
ﺩ.ﺇ1,425 per night
  1. Entire home
  2. Placida
Sunny Daze: Beachfront on Little Gasparilla Island
ﺩ.ﺇ1,049 per night
  1. Entire home
  2. Placida
Nutmeg Cottage on LGI: Gulf views and beach access
ﺩ.ﺇ1,328 per night
  1. Entire home
  2. Placida
Oceanfront Serenity: Beachfront with private dock
ﺩ.ﺇ1,690 per night
  1. Entire home
  2. Placida
Seadated on Little Gasparilla Island
ﺩ.ﺇ1,781 per night
  1. Entire home
  2. Placida
La Te Da Beach House Little Gasparilla Island
ﺩ.ﺇ1,249 per night
  1. Entire home
  2. Placida
Surf's Up: Beachfront on a tropical island!
ﺩ.ﺇ1,551 per night
SUPERHOST
No reviews yet
  1. Entire home
  2. Placida
Placida Paradise
ﺩ.ﺇ1,286 per night
  1. Entire home
  2. Placida
Sea Song 4 Beds 4 Baths Water Front house
ﺩ.ﺇ1,796 per night
  1. Entire home
  2. Placida
Beach to Bay Getaway on Little Gasparilla Island
ﺩ.ﺇ1,388 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.


How do I get around Gasparilla Island?

Gasparilla Island’s nearest major airport is the Southwest Florida International Airport (RSW) outside Fort Myers, about 90 minutes away. However, several airlines maintain connecting air routes to the closer Charlotte County Airport (PGD) in Punta Gorda, just under an hour away. If you’re arriving in southwest Florida by air, using a shuttle service for transport from the airport onto the island is the easiest way to complete the final leg of the journey. Gasparilla Island is sparse when it comes to the variety of amenities and attractions available — its largest community, Boca Grande, spans only a few blocks. For these reasons, it is recommended to get around on foot once you’re on the island, or do as the locals do and travel to Gasparilla Island’s farther reaches via golf cart.

Opt to charter a boat and stay on Little Gasparilla Island for an even more subdued beach experience. Sprawling sandy coastlines span the entire Gulf side of the island, making walking between your Little Gasparilla Island rental and the beach a snap.


When is 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.


What are the 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.