Gasparilla Island vacation rentals

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Popular amenities for Gasparilla Island vacation rentals

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!

DarlaRating, 5 stars1 week ago
My mom and I came down for a long weekend and stayed at John’s place and we were thoroughly impressed! It was the nicest Air BnB I’ve stayed in! It was in a perfect location, walking distance to the beach and many restaurants and right across from a trolley stop too. The beds and bedding were SO comfy, that was probably the best I’ve ever slept in an Air BnB. The towels were oversized and fluffy, you wouldn’t think things like that would make a difference but they do. Everything was absolutely spotless and clean, all of the bedding and towels smelled fresh and clean too. They provided everything you could need, from toiletries and a hair dryer, to everything in the kitchen, to any beach gear that was needed. The house itself is very clean, comfy and cozy and you can tell they take pride in their place just from the landscaping outside, it makes it so pretty! We will definitely be back!
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

PeytonRating, 5 stars9 months ago
Sheryl’s responsiveness and care for us was unmatched. We had an issue with the property that she resolved immediately and even called me personally to make sure my friends and I were taken care of. Great location and outstanding customer service.
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, 117 reviews

* * Endless Summer * * Beach, Unique & Comfort

MarkoRating, 5 stars2 weeks ago
The place was clean and very nicely decorated and furnished. Really enjoyed our stay and would definitely come again.
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

MarleneRating, 5 stars7 months ago
This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!
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

TayaRating, 5 stars3 months ago
Jaime’s place was fabulous! It was spacious and super-comfortable ~ plenty of indoor and outdoor space to hang out, and such a short walk to the beach. The kitchen was well-equipped for cooking, the wifi was fast and the street was quiet. Jaime was very responsive with any questions and easily accommodated our request for early check-in. The stay far exceeded our expectations! We didn’t want to leave the Airbnb :) though we did because it was nearby so much beauty! Thank you, Jaime!
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

MandiRating, 5 stars7 months ago
great place to stay...room was clean, very short walk to the beach, many items in the room available to use (numerous beach chairs, beach umbrellas, life jackets, ect) would definitely stay again!
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

WilliamRating, 5 stars1 month ago
My son and his best friend stayed in Unit A recently and had a terrific time. Unit A is nicely appointed and updated, and was very comfortable for the 3 of us. We especially enjoyed the updated kitchen and the nice deck right out the front door. The deck is a super peaceful place to sit, and we saw many different birds from there including nesting Ospreys and a large American Egret that landed right on the deck railing while we were out there. The common area amenities are fantastic - table tennis, bean toss, and a super nice area to grill out and enjoy the space with friends or our neighbors in the same building as we did several times. We had such a good time that we're planning a return trip next year. Very highly recommended!!
Superhost
Home in Captiva
4.83 out of 5 average rating, 12 reviews

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

CoryRating, 5 stars3 months ago
We cannot say enough about this house! Beautiful, spacious and equipped with anything you could need! Walked out the back door right to the beach! Shelling was so fun and we spent so much time enjoying the sun and sand! A Christmas to remember! Thank you!!

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

GabrielaRating, 5 stars1 day ago
Our stay was truly 10/10! The house was beautiful and exactly like the photos. Trinh was incredibly responsive and provided clear instructions for check-in and check-out. The location was great, with plenty of nearby food spots. The pool made it the perfect beach getaway!⭐️⭐️⭐️⭐️
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

JanellRating, 5 stars1 month ago
We loved the home. It was nice, clean and felt very homey. Had just enough, but not too much. Having all the linens and soaps was very nice and helpful. My dad who has a bad back loved the recliner in the living room. The beds were very comfortable. Even though we didn't get a chance to use it, It was nice having pods for the Keurig available to use. Gina and Sam were very nice, accommodating and responsive. Would definitely stay again.
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

CarrieRating, 5 stars6 days ago
The house was fabulous and better than the photos! We had family staying at the Hyatt Regency and this was the perfect location to meet up and be close. As a family, (ages 13-47) we spent the entire day at the house and everyone agreed, it was better than the Hyatt resort! There is a Publix grocery store and several many restaurants within an 8 minute drive. Also, I swoon for the hammock between two Pine trees. If we are lucky, we will come back for another stay!
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

JeffRating, 5 stars3 days ago
Very nice home, plenty of space for larger family. We used the heated pool everyday. Stores within 5-10 driving minutes of property. Would definitely rent in future
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

RachelRating, 5 stars9 months ago
Perfect time at Blue Abaco! Lovely villa, clean and comfortable, with everything you could need - real home away from home. Plenty space for our family of 4. Everyone enjoyed pool overlooking waterway! Vesteva Vacation Rentals great with communication too. Within easy driving distance - 5 mins- of local shops/restaurants. So could comfortably walk to shops too. Only short drive to Cape Coral Water Park - about 10 mins and about 20/30 minute drive to lovely Fort Myers beach. Located in quiet neighbourhood so really relaxing. Would highly recommend and would certainly do a return visit
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

DianeRating, 5 stars1 month ago
We loved our stay in Cape Coral cottage. The location could not be beat. Close to Cape Coral Parkway and 47th Terrace, the heart of the downtown scene. Tons of restaurants, shops, and bars. Just about everywhere we went was dog friendly on their patios. Angel, our host, was very responsive, never intrusive. She is an excellent host.
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.

DebraRating, 5 stars2 weeks ago
We had a great time. Loved the location, it was close to pretty much everything. Our two 4 pound, Emotional Support Yorkie’s loved the screened in lanai. They would go out there to play and to get some warm sunshine. It was really cute! I love the laundry room, it was perfect and so convenient, right outside the lanai! The two bathrooms were really nice… They both were beautifully remodeled. All in all… our stay was great and we enjoyed it very much. Thank you Angel. We appreciate it. Debbie, Bob, Luci, and Tito.
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, 45 reviews

LILY'S BEACH HOUSE - POOL AND DIRECT RIVER ACCESS

BriRating, 5 stars2 weeks ago
The place was so clean & spacious. Everything was so easy from checking in, to checking out. My kids loved the pool and fishing right out back. I have 0 complaints & I will return next year :)

Beach house rentals in Gasparilla Island

Top guest favorite
An aerial view captures the lush greenery of North Captiva Island, dotted with various houses and surrounded by pristine sandy beaches. The distant shoreline meets the calm waters, reflecting the sky's soft clouds, creating a peaceful coastal scene.
Home in Captiva
5 out of 5 average rating, 20 reviews

Tropical Family Oasis: Pool, Spa, Golf Cart

MollyRating, 5 stars4 days ago
We had a great time at North Tortuga - equally relaxing & inviting!
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!

ArleneRating, 5 stars3 weeks ago
we had a wonderful time at Robert's place. Everything was as described. the island is a perfect getaway for anyone that wants to go on an adventure and get away from the hustle and bustle. The kitchen had everything you would need to cook, it was perfect! Everything was well thought of in this home. On a side note, golf carts need to be booked months in advance and are pretty pricey and we hoped to walk around the island but we're told upon checkin that was not allowed. we could only go to the beach and back to the property. You could walk along the beach though.
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

TiffanyRating, 5 stars8 months ago
This wasn't our first time staying, still wish we could give 10 stars. We will definitely be back again in the future!
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

AlexandraRating, 5 stars1 month ago
Dior’s place was clean and comfortable. Bed was comfortable. Sheets and towels were nice. Beach amenities were helpful. Short walk to pool, beach, a few restaurants and a trolley stop to the village.
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 !

RachelRating, 5 stars3 weeks ago
Impeccably clean and wonderful place to stay! Steve was super responsive, very helpful to us and lovely to work with. Would definitely stay here again and strongly recommend this place to other travelers!
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

JulieRating, 5 stars1 month ago
Super location. So quiet. Very close to the beach. Alan was so responsive and understanding of our flight changes. Lots of local recommendations.
Guest favorite
Home in Fort Myers Beach
4.95 out of 5 average rating, 21 reviews

Stay and Play by the Bay

EllizaRating, 5 stars1 week ago
We had a great time staying here! The pool was great and we loved being right on a channel. 6 people fit in this place comfortably. We were able to walk to everything with ease. The only downside to this area was how busy it was and the loud construction sites, however this is was at no fault of the host! Highly recommend!
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

David & PamRating, 5 stars2 weeks ago
A week at Rodney’s just wasn’t enough! We’ve stayed in a lot of Airbnb properties before, but this was definitely among the top. It felt “beachy” but elegant, complete with everything you need in the kitchen and beach essentials. Lots of closet, space and places to put your stuff, if you are staying for a longer period. The location was perfect. You are never more than 5-10 minutes by car for anything that you need in Nokomis, Venice and further north. I love that you can walk to the popular, fun restaurants, as well as to the beach! This is definitely one of the best properties in the area! I almost don’t want to tell anybody about it so it doesn’t stay too booked ha ha. And if you have a bike, the bike lane is right there, and the area is bike friendly. Rodney was extremely communicative and a gracious host. We will definitely be returning!

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