Gasparilla Island Holidays

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Top hotels in Gasparilla Island

Boca Grande Hotel

Boca Grande Hotel

5800 Gasparilla Road Boca Grande FL
Fully refundableReserve now, pay when you stay
S$179
22 Sept - 23 Sept
includes taxes & fees
Boca Grande Hotel
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
S$277
14 Oct - 15 Oct
includes taxes & fees
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

15951 Captiva Drive Captiva FL
Fully refundableReserve now, pay when you stay
S$442
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing ..."

Reviewed on 20 Sept, 2026

Tween Waters Island Resort & Spa
See all 8,555 properties in Gasparilla Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Gasparilla Island attractions

An aerial view of a coastal resort with a beach, water bodies, and a golf course.

Gasparilla Island State Park

9.4/10 (93 reviews)
Wander Gasparilla Island State Park's pristine shores and historic 1890 lighthouse. Spot dolphins from the beach or explore the lighthouse museum during winter's prime shelling season.
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A rocky shoreline with waves crashing against the rocks and a plant in the foreground.
Photo by Gary-Heather Kobza

Boca Grande Beaches

9.4/10 (59 reviews)
Boca Grande Beaches offer pristine white sands and turquoise waters away from tourist crowds. Spend a day shelling along the shoreline or exploring the nearby historic lighthouse on Gasparilla Island.
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A sandy beach with a lighthouse and palm trees.

Boca Grande Lighthouse Museum

9.4/10 (33 reviews)
This 1890 lighthouse, the oldest structure on Gasparilla Island, houses a maritime museum with local artefacts. Explore exhibits on Calusa Native Americans while enjoying spectacular Gulf of Mexico views.
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Whidden's Marina

9.6/10 (12 reviews)
This 1926 marina captures the vintage charm of Gasparilla Island with its small maritime museum and historic atmosphere. Experienced captains offer access to legendary tarpon fishing grounds during the spring migration.
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St Andrews Episcopal Church

7.0/10 (4 reviews)
This historic church in Boca Grande offers spiritual refuge amid lush Florida greenery. Explore the serene Memorial Garden with its full-sized labyrinth after attending the welcoming Sunday morning service.
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Our Lady of Mercy Catholic Church

7.6/10 (5 reviews)
This intimate Catholic church in Boca Grande offers a peaceful sanctuary for prayer and reflection. Join the welcoming parish community for morning Mass or spend quiet moments in its serene setting.
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Boca Grande Historical Society and Museum

9.2/10 (12 reviews)
This intimate museum chronicles Gasparilla Island's transformation from phosphate hub to coastal haven through artefacts and photographs. Explore the recreated 1940s home showcasing Boca Grande's rich maritime heritage.
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Lighthouse United Methodist Church

8.8/10 (3 reviews)
This welcoming Methodist church serves as a spiritual anchor for the Boca Grande community. Visitors can experience its warmest embrace during the popular Christmas Eve candlelight service.
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Frequently asked questions

How much does a Gasparilla Island holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Gasparilla Island from just . And the more you bundle, the more dollars you save. Your dream holiday has never been more affordable.
How do I get a cheap travel package to Gasparilla Island?
Booking a Gasparilla Island holiday package with Expedia is such a simple way to save. We have more than 550 air carriers and 1,000,000 hotels worldwide. With such an extensive range to pick from, you'll have no worries creating your ideal adventure.
Where should I stay in Gasparilla Island?
With so much to do in Gasparilla Island, it'd be convenient for you to stay close to its attractions. Gasparilla Island State Park, Boca Grande Beaches and Boca Grande Lighthouse Museum are some interesting ones to put on your must-see list.
What are the top hotels in Gasparilla Island?
Get your escape off to a fantastic start by reserving a room at Sundown 17 2 Bedroom Villa By Redawning. It's one of most sought-after properties in Gasparilla Island. Another leading option is Seagrape Colony 10 3 Bedroom Home By Redawning.
How far in advance should I book my Gasparilla Island holiday?
Reserving your flights early with Expedia means one less thing to worry about. Most carriers display prices up to a year in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, low prices to Gasparilla Island sometimes become available in the weeks leading up to departure.
What does an Expedia Gasparilla Island travel package include?
That's up to you. You can pick from a range of Gasparilla Island bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your dream Gasparilla Island getaway looks like, get set to save!
What should I know before booking a Gasparilla Island travel package?
Find deals that fit your budget with an Expedia package. Flights, hotels, rental cars — we have everything you need to plan your break. You'll save loads just for combining your bookings. Whether you're embarking on a ski adventure or venturing someplace warm, your perfect getaway is only a few clicks away.
Can I choose my airline with a Gasparilla Island Expedia holiday package?
Yes, and with more than 550 airlines to choose from around the world, you have loads of choice. Have a look through the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Gasparilla Island holiday package?
Certainly, and we'll help you every step of the way. You may be able to change or cancel your Gasparilla Island holiday package at no cost if you booked in the last 24 hours. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.