Little Gasparilla Island Vacation Packages

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Top Little Gasparilla Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $1,212, price is now CA $805 per person
CA $805
per person
Jul 20 - Jul 25
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
That staff was exceptional... my brother became ill when we arrived and they couldn't have been more caring or thoughtful

Reviewed on Apr 28, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $2,073, price is now CA $1,284 per person
CA $1,284
per person
Jul 10 - Jul 15
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,007 reviews)
Great boutique resort. Had the perfect babymoon.

Reviewed on Apr 25, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,311, price is now CA $813 per person
CA $813
per person
Jun 20 - Jun 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (758 reviews)
The front desk was not staffed adequately-has to wait 10-15 minutes and ask another staff person so that could check in.

Reviewed on Apr 29, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,622, price is now CA $1,144 per person
CA $1,144
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (843 reviews)
It was amazing! Chantel helped us check in and the process was smooth. Overall we had a blast!

Reviewed on Apr 28, 2026

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
South End
Price was CA $1,552, price is now CA $1,121 per person
CA $1,121
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,751 reviews)
The space was clean, the pool was great, location on the beach was awesome. They do nickel and dime you a lot on the resort fee ($50!), parking ($40), and extra beach chairs ($7/chair), so beware of that even when you book through Expedia. But overall the place was really cool, and the 2 queens with the pullout bed option was great for families. Really solid.

Reviewed on Apr 29, 2026

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Little Gasparilla Island Hotel Deals

TEMPORARY CLOSED BECAUSE HURRICANE MILTON SEVERE DAMAGE

TEMPORARY CLOSED BECAUSE HURRICANE MILTON SEVERE DAMAGE

Placida FL
9/10 Wonderful! (40 reviews)
Island life
Great place to unplug and wash off some of the monotony life. Exploring the island is a great retreat for those that truly want to "unplug" This house is modern and has neat features such as steam shower and sauna. The 2nd bedroom could use repairs from water damage the shower has caused. Hopefully ...

Reviewed on Jul 4, 2024

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TEMPORARY CLOSED BECAUSE HURRICANE MILTON SEVERE DAMAGE
Salty Mermaid on Little Gasparilla Island! Come get salty!

Salty Mermaid on Little Gasparilla Island! Come get salty!

Placida FL
10/10 Exceptional! (8 reviews)
The house had a lot of extras making it super comfy and easy to stay in. The proximity to the beach was wonderful.We were surprised that it looked like some of the guests before us did not take good care of some of the amenities, like the beach gear (snorkels and masks, in particular) Maybe a sign ...

Reviewed on Mar 17, 2026

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Salty Mermaid on Little Gasparilla Island! Come get salty!
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
5500 Sunseeker Way Punta Gorda FL
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 7 to May 8
CA $247
CA $346 total
May 7 - May 8
includes taxes & fees
9.2/10 Wonderful! (2,529 reviews)
Todo maravilloso!!!! Repetiría con gusto!!! Sus apartamentos modernos , limpios, súper bien decorados . La atención excelente! Muchas ofertas de entretenimiento, variedad en la comida y coctelería. Todo nuevo , limpio, agradable!!! Lo adoré!

Reviewed on Apr 29, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
See all 6,221 properties in Little 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.
All Inclusive Vacations
All Inclusive Vacations
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Discover the most popular places to visit in Little Gasparilla Island

Don Pedro Island State Park

Commune with nature and explore the great outdoors at Don Pedro Island State Park during your travels in Placida. Wander the beautiful beaches in this relaxing area.

Don Pedro Island State Park

Gasparilla Marina

Explore the waterfront in Placida with a trip to Gasparilla Marina. Wander the beautiful beaches in this family-friendly area.

Gasparilla Marina

What to do in Little Gasparilla Island

Wild dolphins on Charlotte Harbor!

Charlotte Harbor: Dolphin Discovery Day Cruise

CA $81
per adult
Charlotte Harbor: Dolphin Discovery Day Cruise
Sunset Tiki Boat Cruise

Sunset Tiki Boat Cruise (BYOB)

CA $95
per adult
Sunset Tiki Boat Cruise (BYOB)
See all activities in Little Gasparilla Island

Frequently asked questions

Can I cancel my flight booking to Little Gasparilla Island due to COVID-19?
Head to our helpful Customer Service Portal for details about making changes to your flight because of COVID-19. Make sure you also look over the terms and conditions of your chosen airline before you book your seat.
What's the best way to find cheap flights to Little Gasparilla Island that have flexible change policies?
It's as easy as counting to three with Expedia. Step 1: Type in your travel dates and click on "Search." Next step? Check "No change fee" directly below the "Flexible change policies" heading on the top left of your screen. Step 3. Score a cheap and flexible flight to Little Gasparilla Island.
What are some of the general tips for travelers to Little Gasparilla Island during the COVID-19 outbreak?
COVID-19 has changed the world in all sorts of ways, including how we're able to travel safely. The following tips will help you navigate the new challenges and prepare you for your journey to Little Gasparilla Island:
  • Research if any travel restrictions apply to your destination and origin before booking your flight. Also check if there are any special conditions you'll need to follow on arrival, such as proof of a negative COVID-19 test.
  • When you go through airport checkpoints, keep your face mask on. You will be required to briefly lower it for ID purposes. Anyone refusing to wear a mask may be denied entry or boarding.
  • You're no longer required to hand your boarding pass directly to a TSA employee. Rather, you should position the pass on the scanner and then hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will need to be removed from your bag at the X-ray machine for screening.
  • To minimize handling during screening, place items such as your loose change and phone into your carry-on instead of the bins.
  • Separate any food you have for screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA employee to handle and inspect your belongings.

Which airlines fly to Little Gasparilla Island?
Delta runs flights into or near Little Gasparilla Island, including 460 that travel to Southwest Florida Intl. Airport (RSW) each month. Pick your travel dates and then book your seat early for an awesome deal.
How can I find cheap tickets to Little Gasparilla Island?
To nab a terrific deal to Little Gasparilla Island, book ahead of time. Also consider using Expedia's "flexible dates" link at the top of your search results. This will compare prices for the days around your travel dates. In the last seven days, was the lowest price for a flight to Little Gasparilla Island.
How much is a flight to Little Gasparilla Island?
In the last seven days, round-trip flights to Little Gasparilla Island sold for as low as and reached a maximum cost of . For one-way trips out of (), the lowest amount paid during this same period was .
What are the most popular airports to fly into in Little Gasparilla Island?
Start arranging your Little Gasparilla Island journey by booking a fare on one of the 3044 flights each month to Southwest Florida Intl. Airport (RSW). This is the region's principal gateway.
When is the cheapest time to fly to Little Gasparilla Island?
If you'd rather spend your hard-earned vacation dollars experiencing Little Gasparilla Island rather than on flying there, leave early in the week. The most economical day to fly is generally Tuesday, with Monday close behind. With many folks traveling over the weekend, Saturday tends to have the costliest fares.
How much is a plane ticket to Little Gasparilla Island?
In the last seven days, journeys to Little Gasparilla Island cost between and . Prices depend on the time of departure, carrier, cabin class and when the fare is booked.
Which airlines with flights to Little Gasparilla Island employ COVID-19 cleanliness policies?
In response to the current pandemic, airlines have adopted enhanced measures and standards to help their passengers and staff fly with confidence. Some of these carriers include:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.