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.

Guest favorite

Home in Englewood

4.98 out of 5 average rating, 106 reviews

PRIME 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

$439 per night
Guest favorite

Cottage in Matlacha

4.88 out of 5 average rating, 130 reviews

Mojito 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

$95 per night
Guest favorite

Apartment in Boca Grande

4.89 out of 5 average rating, 178 reviews

Downtown 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

$153 per night

Popular amenities for Gasparilla Island vacation rentals

Gasparilla Island beach vacation rentals

Guest favorite

Home in Englewood

4.99 out of 5 average rating, 101 reviews

Paradise on the Bay

Nov 17 – 24

$363 per night
Guest favorite

Home in Matlacha

5.0 out of 5 average rating, 137 reviews

The Secret Island Retreat HeatedPool/4b/open water

Apr 29 – May 6

$403 per night
Guest favorite

Cottage in Nokomis

4.98 out of 5 average rating, 123 reviews

Staycation Sanctuary - 100% Smoke-Free Property

Jul 19 – 26

$102 per night
Guest favorite

Cottage in Bokeelia

4.99 out of 5 average rating, 106 reviews

Romantic Getaway “Waterside” Dockage~Canal front

May 3 – 10

$176 per night
Guest favorite

Home in Englewood

4.84 out of 5 average rating, 149 reviews

Manasota Key Florida House Rental

Dec 17 – 24

$137 per night
Guest favorite

Home in Matlacha

4.98 out of 5 average rating, 178 reviews

Matlacha Paradise! NEW Waterfront Home-Free Kayaks

Jun 11 – 18

$149 per night
Guest favorite

Cottage in Englewood

4.96 out of 5 average rating, 134 reviews

Family-Friendly Beach Cottage Manasota Key

Oct 17 – 24

$199 per night
Guest favorite

Home in Englewood

4.96 out of 5 average rating, 101 reviews

Waterfront Cottage by Manasota Key

Sep 27 – Oct 4

$130 per night
Superhost

Cottage in Boca Grande

4.87 out of 5 average rating, 85 reviews

Charming beach cottage house with pool.

Apr 23 – 30

$518 per night
Guest favorite

Home in Placida

5.0 out of 5 average rating, 48 reviews

Lu's Lookout~A Beachfront Beauty🤎🌊 🏝 LGI

Sep 4 – 11

$574 per night
Superhost

Villa in Boca Grande

4.89 out of 5 average rating, 19 reviews

Yacht Watch

Nov 15 – 22

$754 per night
Guest favorite

Cottage in Englewood

5.0 out of 5 average rating, 53 reviews

Private Cottage on Manasota Key

Nov 11 – 18

$498 per night

Gasparilla Island house rentals

Superhost

Home in Englewood

4.93 out of 5 average rating, 120 reviews

Stunning Home, Saltwater Heated Pool By the Beach

Sep 9 – 16

$145 per night
Guest favorite

Home in Cape Coral

4.91 out of 5 average rating, 152 reviews

Modern Oasis pool paradise

Nov 17 – 24

$110 per night
Guest favorite

Home in Sarasota

4.96 out of 5 average rating, 127 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Jul 19 – 26

$111 per night
Guest favorite

Home in Port Charlotte

4.98 out of 5 average rating, 137 reviews

Cute cheery peaceful canal home fishing fun 3B/2B

Nov 24 – Dec 1

$101 per night
Guest favorite

Home in Fort Myers

4.85 out of 5 average rating, 585 reviews

Tiny house 5 miles from Sanibel / free amenities

Jul 14 – 21

$99 per night
Guest favorite

Home in Englewood

4.95 out of 5 average rating, 111 reviews

"Lighthouse" 7 mins from Beach, direct gulf access

Sep 2 – 9

$155 per night
Guest favorite

Home in Rotonda West

4.9 out of 5 average rating, 151 reviews

❤ROTONDA RETREAT❤*Spacious*Fully Furnished*Pool*

Oct 23 – 30

$155 per night
Guest favorite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Sep 23 – 30

$400 per night
Guest favorite

Home in Captiva

5.0 out of 5 average rating, 34 reviews

My Sea Shack~ 1 minute to beach, SH Club, G-Cart

Nov 16 – 23

$262 per night
Superhost

Home in Placida

4.95 out of 5 average rating, 39 reviews

CocoHut~Tub

Dec 14 – 21

$742 per night
Guest favorite

Home in Englewood

5.0 out of 5 average rating, 14 reviews

Vacation Condo- Beach Access!

Aug 29 – Sep 5

$305 per night
Guest favorite

Home in Placida

5.0 out of 5 average rating, 12 reviews

Family Tides on LGI - Golf Cart Included

Sep 9 – 16

$333 per night

Beach house rentals in Gasparilla Island

Guest favorite

Home in Englewood

4.78 out of 5 average rating, 141 reviews

Custom Built Manasota Beach Home with Pool

Dec 6 – 13

$261 per night
Guest favorite

Home in Port Charlotte

4.82 out of 5 average rating, 234 reviews

Bright and sunny Port Charlotte home

Sep 14 – 21

$113 per night
Superhost

Home in Cape Coral

4.84 out of 5 average rating, 161 reviews

One step closer to paradise.!!!

May 19 – 26

$102 per night
Guest favorite

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

$544 per night
Guest favorite

Home in Captiva

5.0 out of 5 average rating, 65 reviews

Beachfront | Pvt Fishing Dock, Shelling, Sunrises

Apr 26 – May 3

$775 per night
Guest favorite

Home in Cayo Costa

4.9 out of 5 average rating, 21 reviews

Cayo Costa Paradise Found

Jul 23 – 30

$639 per night
Superhost

Home in Englewood

4.86 out of 5 average rating, 28 reviews

New Listing! Resort-like Oasis on Canal

Sep 29 – Oct 6

$172 per night
Guest favorite

Home in Englewood

4.93 out of 5 average rating, 81 reviews

Florida Gulf Coast Get-Away

Oct 11 – 18

$100 per night
Superhost

Home in Placida

5.0 out of 5 average rating, 5 reviews

Just listed! BRAND NEW Coastal Sol on Palm Island!

May 8 – 15

$302 per night
Guest favorite

Home in Placida

5.0 out of 5 average rating, 22 reviews

Close to beaches, canal view, golf, fishing

Sep 21 – 28

$159 per night
Guest favorite

Home in Venice

5.0 out of 5 average rating, 8 reviews

Oasis - The Agave

Apr 30 – May 7

$115 per night
Guest favorite

Home in Captiva

4.92 out of 5 average rating, 99 reviews

Blue Laguna - Vacation in paradise!

Aug 11 – 18

$491 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