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.
Home in Englewood
4.98 out of 5 average rating, 106 reviewsPRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!
LOCATION! Best on island! Family & pet friendly (pets require approval & $125 per pet fee). Just steps to our private beach, 1 mile to bars & restaurants w/ free shuttle to beaches, bars, restaurants! Amazing beds, comfy huge couch, flat screen smart TV's in every bedroom with Xfinity & free fast Wifi. Private over sized lot & lanai w/ new furniture, outdoor quiet oasis w/ hammock, 2 dining tables, chairs & gas grill. 3 bikes, beach chairs, towels, and toys. 1 mile to Manasota Key public beach.
Dec 9 – 16
Cottage in Matlacha
4.88 out of 5 average rating, 130 reviewsMojito Island Cottage
Update: In September we were affected by Hurricane Ian. We had just over 5 feet of flooding in our treasured cottage. We have worked tirelessly to put everything back together. All new tile, walls, electric, lighting, furniture, and we even improved the bathroom! Spacious tropical home with water view from our back yard lanai. Boat Dock with Cleaning Fish Station, BBQ beautiful sunsets with fish jumping in our back yard. New large kitchen and one block from art galleries, restaurants and bars.
Sep 27 – Oct 4
Apartment in Boca Grande
4.89 out of 5 average rating, 178 reviewsDowntown Boca Grande Efficiency Flat#3-Special Rt
We survived Ian and are ready to host you! A great efficiency, 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 Air BnB and receive a 10% discount on golf cart and bike rentals. You’ll love my place because of the location, and the neighborhood.
Aug 8 – 15
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gasparilla Island vacation rentals
Gasparilla Island beach vacation rentals
Home in Englewood
4.99 out of 5 average rating, 101 reviewsParadise on the Bay
Nov 17 – 24
Home in Matlacha
5.0 out of 5 average rating, 137 reviewsThe Secret Island Retreat HeatedPool/4b/open water
Apr 29 – May 6
Cottage in Nokomis
4.98 out of 5 average rating, 123 reviewsStaycation Sanctuary - 100% Smoke-Free Property
Jul 19 – 26
Cottage in Bokeelia
4.99 out of 5 average rating, 106 reviewsRomantic Getaway “Waterside” Dockage~Canal front
May 3 – 10
Home in Englewood
4.84 out of 5 average rating, 149 reviewsManasota Key Florida House Rental
Dec 17 – 24
Home in Matlacha
4.98 out of 5 average rating, 178 reviewsMatlacha Paradise! NEW Waterfront Home-Free Kayaks
Jun 11 – 18
Cottage in Englewood
4.96 out of 5 average rating, 134 reviewsFamily-Friendly Beach Cottage Manasota Key
Oct 17 – 24
Home in Englewood
4.96 out of 5 average rating, 101 reviewsWaterfront Cottage by Manasota Key
Sep 27 – Oct 4
Cottage in Boca Grande
4.87 out of 5 average rating, 85 reviewsCharming beach cottage house with pool.
Apr 23 – 30
Home in Placida
5.0 out of 5 average rating, 48 reviewsLu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI
Sep 4 – 11
Villa in Boca Grande
4.89 out of 5 average rating, 19 reviewsYacht Watch
Nov 15 – 22
Cottage in Englewood
5.0 out of 5 average rating, 53 reviewsPrivate Cottage on Manasota Key
Nov 11 – 18
Gasparilla Island house rentals
Home in Englewood
4.93 out of 5 average rating, 120 reviewsStunning Home, Saltwater Heated Pool By the Beach
Sep 9 – 16
Home in Cape Coral
4.91 out of 5 average rating, 152 reviewsModern Oasis pool paradise
Nov 17 – 24
Home in Sarasota
4.96 out of 5 average rating, 127 reviewsSarasota Florida -Wild Orchid Creek Cottage Home
Jul 19 – 26
Home in Port Charlotte
4.98 out of 5 average rating, 137 reviewsCute cheery peaceful canal home fishing fun 3B/2B
Nov 24 – Dec 1
Home in Fort Myers
4.85 out of 5 average rating, 585 reviewsTiny house 5 miles from Sanibel / free amenities
Jul 14 – 21
Home in Englewood
4.95 out of 5 average rating, 111 reviews"Lighthouse" 7 mins from Beach, direct gulf access
Sep 2 – 9
Home in Rotonda West
4.9 out of 5 average rating, 151 reviews❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*
Oct 23 – 30
Home in Englewood
5.0 out of 5 average rating, 25 reviews"Lost Loon" Oceanfront Cottage by Roxy Rentals
Sep 23 – 30
Home in Captiva
5.0 out of 5 average rating, 34 reviewsMy Sea Shack~ 1 minute to beach, SH Club, G-Cart
Nov 16 – 23
Home in Placida
4.95 out of 5 average rating, 39 reviewsCocoHut~Tub
Dec 14 – 21
Home in Englewood
5.0 out of 5 average rating, 14 reviewsVacation Condo- Beach Access!
Aug 29 – Sep 5
Home in Placida
5.0 out of 5 average rating, 12 reviewsFamily Tides on LGI - Golf Cart Included
Sep 9 – 16
Beach house rentals in Gasparilla Island
Home in Englewood
4.78 out of 5 average rating, 141 reviewsCustom Built Manasota Beach Home with Pool
Dec 6 – 13
Home in Port Charlotte
4.82 out of 5 average rating, 234 reviewsBright and sunny Port Charlotte home
Sep 14 – 21
Home in Cape Coral
4.84 out of 5 average rating, 161 reviewsOne step closer to paradise.!!!
May 19 – 26
Home in Englewood
5.0 out of 5 average rating, 51 reviews"Peaceful Sol" - large 3 bd, just steps to BEACH!
Jan 27 – Feb 3
Home in Captiva
5.0 out of 5 average rating, 65 reviewsBeachfront | Pvt Fishing Dock, Shelling, Sunrises
Apr 26 – May 3
Home in Cayo Costa
4.9 out of 5 average rating, 21 reviewsCayo Costa Paradise Found
Jul 23 – 30
Home in Englewood
4.86 out of 5 average rating, 28 reviewsNew Listing! Resort-like Oasis on Canal
Sep 29 – Oct 6
Home in Englewood
4.93 out of 5 average rating, 81 reviewsFlorida Gulf Coast Get-Away
Oct 11 – 18
Home in Placida
5.0 out of 5 average rating, 5 reviewsJust listed! BRAND NEW Coastal Sol on Palm Island!
May 8 – 15
Home in Placida
5.0 out of 5 average rating, 22 reviewsClose to beaches, canal view, golf, fishing
Sep 21 – 28
Home in Venice
5.0 out of 5 average rating, 8 reviewsOasis - The Agave
Apr 30 – May 7
Home in Captiva
4.92 out of 5 average rating, 99 reviewsBlue Laguna - Vacation in paradise!
Aug 11 – 18
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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