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Gasparilla Island vacation rentals

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Vacation rentals for every style

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Popular amenities for Gasparilla Island vacation rentals

Free parking on premises
Beachfront
Gym
BBQ grill
Laptop-friendly workspace

Gasparilla Island beach vacation rentals

Top guest favorite
A comfortable living space features a blue sectional sofa and a patterned armchair, complemented by a wooden coffee table. Light streams in through a window with blinds, while a welcoming entry door adds to the serene ambiance.
Villa in Sarasota
4.96 out of 5 average rating, 169 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Superhost
A panoramic view of a sandy beach extends under a bright blue sky streaked with wispy clouds. Gentle waves lap at the shore, and a few figures can be seen walking along the water's edge. Sunlight highlights the fine, white sand.
Home in Sarasota
4.89 out of 5 average rating, 92 reviews

Renovated Beachhouse Private Beach Access, Unit S

Top guest favorite
A bright living area features a light beige sectional sofa with decorative blue cushions, accompanied by a coordinating armchair. A wooden coffee table sits at the center, while natural light filters through large windows, illuminating the space and enhancing the neutral decor.
Home in Naples
4.97 out of 5 average rating, 118 reviews

* * Endless Summer * * Beach, Unique & Comfort

Guest favorite
An aerial view reveals a mid-century vacation villa surrounded by lush greenery and open spaces, with the coastline and sandy beach visible in the distance. The calm ocean water stretches towards the horizon beneath a partly cloudy sky.
Condo in Venice
4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

Guest favorite
A gravel pathway is bordered by ornamental grasses leading to a wooden bench, providing a peaceful outdoor space. Utility poles and nearby houses are visible in the background, with a glimpse of a driveway and a boat in the distance.
Home in Nokomis
4.88 out of 5 average rating, 32 reviews

Beach house

Superhost
A light-filled primary bedroom features a king-size bed with a multicolored striped blanket, positioned near a window showcasing views of the Gulf of Mexico. A ceiling fan is present, and a flat-screen TV is mounted on the wall opposite the bed.
Condo in Sarasota
4.9 out of 5 average rating, 10 reviews

Beachfront - Siesta Key 2 BR walk out to beach

Guest favorite
An outdoor deck features colorful seating arrangements with two turquoise chairs and a small table set against a backdrop of lush greenery. A patio umbrella provides shade, and a tropical-patterned rug adds a vibrant touch to the space.
Apartment in Manasota Key
4.92 out of 5 average rating, 12 reviews

DolphinCove 5035A Turtle Cove

Superhost
Home in Captiva
4.83 out of 5 average rating, 12 reviews

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

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Gasparilla Island house rentals

Superhost
A modern kitchen is highlighted by a spacious island with four bar stools. The area features pendant lighting and a large window offering views of the screened pool area. Soft tones and natural light create a welcoming space with sleek cabinetry.
Home in Cape Coral
4.85 out of 5 average rating, 156 reviews

LUXURIOUS LARGE OPEN OCEAN BLUE POOL VACATION HOME

Top guest favorite
A single-story cottage features a light blue exterior with a brown roof, framed by lush green grass and flowering plants. A small porch with railing provides entry, and a driveway leads to an attached garage on the left side.
Home in Punta Gorda
4.93 out of 5 average rating, 72 reviews

At Home in Seahorse Themed, Cozy Cottage

Guest favorite
A cozy living area features a vintage-style wood-burning stove with a brick surround. A round dining table is positioned nearby, complemented by neutral-toned chairs. A large plant adds a touch of greenery, and a circular mirror reflects light in the space.
Home in Bonita Springs
4.93 out of 5 average rating, 141 reviews

Pool house near Hyatt Regency Coconut Point

Top guest favorite
The entrance of the home is framed by lush greenery and vibrant flowering plants. The façade features large windows that provide ample natural light, while a covered porch welcomes guests. A clear blue sky complements the fresh and inviting exterior.
Home in North Port
4.79 out of 5 average rating, 152 reviews

3 bdrm Pool Home / Quiet Cul De Sac

Superhost
A spacious living area is highlighted by high ceilings and large windows allowing natural light to fill the room. A light-colored sectional sofa is arranged around a wooden coffee table on a patterned rug. An open floor plan connects to the dining area and kitchen in the background.
Home in Cape Coral
4.88 out of 5 average rating, 32 reviews

Blue Abaco - Beautiful Waterfront House

Superhost
A well-lit bedroom features a spacious bed adorned with blue decorative pillows. A ceiling fan with light fixtures complements the contemporary style. A flat-screen TV is mounted on the wall, while a dresser offers storage. An en suite bathroom is visible through an open door.
Home in Cape Coral
5 out of 5 average rating, 4 reviews

Cape Cottage

Guest favorite
A spacious bedroom is furnished with a plush bed dressed in soft neutral tones and decorative pillows. Two bedside tables flank the bed, each holding a lamp. Natural light fills the room, highlighting the warm color palette and elegant bedding.
Home in Port Charlotte
4.9 out of 5 average rating, 41 reviews

Charming home near the Beach and Punta Gorda.

Superhost
A vibrant room features a deep blue accent wall adorned with coastal decorations. A bar area with high stools and a small table set for two is visible, alongside a charming wall-mounted map and nautical-themed decor. Large windows allow natural light and views of the outside garden.
Home in Cape Coral
4.87 out of 5 average rating, 46 reviews

LILY'S BEACH HOUSE - POOL AND DIRECT RIVER ACCESS

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Beach house rentals in Gasparilla Island

Superhost
An aerial view captures the island setting, highlighting a private beach alongside lush greenery. Community docks are visible in the lower section, providing access to the bay. The ocean extends in the background, with cloudy skies above offering a serene backdrop.
Home in Placida
5 out of 5 average rating, 8 reviews

Bay view and possible two family rental!

Top guest favorite
An outdoor dining area features a wooden table surrounded by black wicker chairs, positioned on a patio overlooking a canal. The scene is enhanced by greenery, trees, and the bright sky, creating a serene setting for meals or gatherings.
Home in Port Charlotte
5 out of 5 average rating, 13 reviews

Waterfront Escape on canal ocean access kayaks

Superhost
An inviting beach scene features a sun umbrella providing shade over a wooden lounge chair, set upon soft, sandy shores. The clear blue sky contrasts with the tranquil turquoise waters, creating a peaceful atmosphere near the shoreline.
Home in Siesta Key
4.76 out of 5 average rating, 505 reviews

Beachfront Getaway in Siesta Key

Top guest favorite
A cozy living area features a spacious sectional couch adorned with colorful throw pillows. A light wooden coffee table sits in the center, complementing the gray tones of the room. A beach-themed artwork is displayed above the couch, and natural light filters through the nearby window.
Home in Venice
5 out of 5 average rating, 12 reviews

The Beach Is Calling !

Guest favorite
A welcoming living area features two comfortable armchairs positioned near a large wall-mounted television. Bright light enters through the window with white blinds, illuminating the light wood flooring and a decorative shelf. A neutral color palette creates a calming atmosphere.
Home in Fort Myers Beach
4.8 out of 5 average rating, 42 reviews

Life's a Beach Cottage

Guest favorite
Home in Fort Myers Beach
4.95 out of 5 average rating, 21 reviews

Stay and Play by the Bay

Guest favorite
A spacious living area features a comfortable sectional sofa with accent pillows, along with two armchairs. Natural light fills the room through large windows, highlighting a modern area rug. The open layout connects seamlessly to a well-equipped kitchen visible in the background.
Home in Nokomis
4.9 out of 5 average rating, 31 reviews

BeachHouse Getaway-5 minute walk to Nokomis Beach

Guest favorite
A spacious deck overlooks the Gulf, featuring a large dining table surrounded by several chairs. The ocean vista is unobstructed, with gentle waves visible in the distance and palm trees framing the scene.
Home in Bonita Springs
4.98 out of 5 average rating, 52 reviews

Beachfront Oasis

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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