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.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,567, price is now CA $890 per person
CA $890
per person
May 24 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (477 reviews)
Woody is a fantastic host at the main floor pool! What a great hotel!

Reviewed on Mar 3, 2026

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was CA $1,543, price is now CA $903 per person
CA $903
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Tidy room, easy access, good parking, great location.

Reviewed on Mar 2, 2026

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Price was CA $5,994, price is now CA $3,549 per person
CA $3,549
per person
Apr 3 - Apr 8
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Sarasota (SRQ)
9.6/10 Exceptional! (74 reviews)
Everything was excellent!

Reviewed on Feb 28, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was CA $1,698, price is now CA $1,008 per person
CA $1,008
per person
May 24 - May 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Enjoyed the pool area and lazy river. Room was beautiful and spacious. Would definitely stay here again.

Reviewed on Mar 2, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was CA $2,129, price is now CA $1,371 per person
CA $1,371
per person
Apr 25 - May 2
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.8/10 Exceptional! (1,027 reviews)
Great. Awesome room n vuews

Reviewed on Feb 22, 2026

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Little Gasparilla Island Hotel Deals

Bay Watch - Beautiful Bay Views - PRIVATE ISLAND

Bay Watch - Beautiful Bay Views - PRIVATE ISLAND

Placida FL
The price is CA $239 per night from Mar 5 to Mar 6
CA $239
CA $730 total
Mar 5 - Mar 6
includes taxes & fees
9.6/10 Exceptional! (12 reviews)
Great

Reviewed on Feb 12, 2026

Bay Watch - Beautiful Bay Views - PRIVATE ISLAND
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 $254 per night from Mar 22 to Mar 23
CA $254
CA $353 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (1,992 reviews)
We loved our stay! The rooms are fresh and clean, the bed was very comfortable, and the shower is amazing. The room had everything we needed and was very quiet. On the first evening, there was a terrible smell of cigarette smoke coming into our bathroom. I called the front desk and they quickly changed ...

Reviewed on Mar 3, 2026

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
1200 W Retta Esplanade Punta Gorda FL
The price is CA $289 per night from Apr 2 to Apr 3
CA $289
CA $323 total
Apr 2 - Apr 3
includes taxes & fees
9.8/10 Exceptional! (1,114 reviews)
We didn’t get into our rooms until 4:45, check in was at 4:00. Very expensive room to lose any time. I expressed my frustration and the manager told us he could sell our room. A better response would have been to offer a discount or credit towards a local restaurant. And found hair and dirt on the ...

Reviewed on Mar 1, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites
See all 6,231 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.
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Discover the most popular places to visit in Little Gasparilla Island

Gasparilla Marina

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

Gasparilla Marina

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

What to do in Little Gasparilla Island

"The Oasis" Tiki Boat

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.