Cheap flights To Little Gasparilla Island (RSW) from $51

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Cheap Flights to Little Gasparilla Island from $51 One Way, $87 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Sep 4 - Mon, Sep 28
PSM
Portsmouth Intl.
PGD
Punta Gorda Airport
$87 Roundtrip, found 13 hours ago
$87
Roundtrip
found 13 hours ago
Select Allegiant Air flight, departing Fri, Sep 4 from Portsmouth Intl. to Punta Gorda Airport, returning Mon, Sep 28, priced at $87 found 13 hours ago
Mon, Dec 7 - Fri, Dec 11
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Dec 7 from Logan Intl. to Sarasota-Bradenton Intl., returning Fri, Dec 11, priced at $88 found 1 day ago
Sun, Oct 25 - Tue, Nov 3
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Oct 25 from Hopkins Intl. to Southwest Florida Intl., returning Tue, Nov 3, priced at $109 found 1 day ago
Sat, Dec 5 - Sat, Jan 9
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Dec 5 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Jan 9, priced at $132 found 1 day ago
Sat, Aug 29 - Sat, Sep 5
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$145 Roundtrip, found 11 hours ago
$145
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Sat, Aug 29 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Sep 5, priced at $145 found 11 hours ago
Sun, Sep 20 - Tue, Sep 29
BDL
Bradley Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, Sep 20 from Bradley Intl. to Southwest Florida Intl., returning Tue, Sep 29, priced at $152 found 3 days ago
Sat, Oct 3 - Tue, Oct 6
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 3 days ago
$189
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Oct 3 from Logan Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $189 found 3 days ago
Sat, Nov 14 - Tue, Nov 17
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$197 Roundtrip, found 19 hours ago
$197
Roundtrip
found 19 hours ago
Select United flight, departing Sat, Nov 14 from Logan Intl. to Southwest Florida Intl., returning Tue, Nov 17, priced at $197 found 19 hours ago
Sat, Sep 12 - Sat, Sep 19
JFK
John F. Kennedy Intl.
RSW
Southwest Florida Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 12 from John F. Kennedy Intl. to Southwest Florida Intl., returning Sat, Sep 19, priced at $197 found 2 days ago
Sun, Jan 10 - Thu, Jan 14
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Jan 10 from Minneapolis - St. Paul Intl. to Sarasota-Bradenton Intl., returning Thu, Jan 14, priced at $197 found 1 day ago

Little Gasparilla Island Flight Information

Traveling To
Little Gasparilla Island
Destination Airport IATA Code
RSW
Number of Airlines Serving
Airlines
Allegiant Air, Frontier Airlines, Breeze Airways, Sun Country Airlines, Southwest Airlines, United, Delta
Flight Price
$87
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Little Gasparilla Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
4.5-star property

The Perry Hotel Naples

Sep 5 - Sep 12

7 night stay

Boston (BOS) to Fort Myers (RSW)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $963, price is now $548 per person
$548
per person
found 1 day ago
A Wave From it All
2.0-star property

A Wave From it All

Sep 7 - Sep 12

5 night stay

Minneapolis (MSP) to Fort Myers (RSW)

Sun Country Airlines • Coach

Fort Myers (RSW) to Minneapolis (MSP)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,249, price is now $1,446 per person
$1,446
per person
found 1 day ago
Landing Apartments Fort Myers near Olympia Pointe
4.0-star property

Landing Apartments Fort Myers near Olympia Pointe

Sep 5 - Sep 12

7 night stay

Boston (BOS) to Fort Myers (RSW)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $838, price is now $566 per person
$566
per person
found 1 day ago
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Little Gasparilla Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Tropical Villas of Venice Beach
3.5-star property

Tropical Villas of Venice Beach

9.6/10 Exceptional! (260 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $953, price is now $781 per person
$781
per person
found 1 day ago
Was quiet , respectful. If you looking for something bare minimum nothing elaborate this way to go. Staff kind and respectful. Reachable by phone but not on property. Could use more kitchen supplies if you’re planning meals at home. I would book again if had a trip back to Venice

Reviewed on Jul 19, 2026

Escape Coastal Resort on Casey Key
2.5-star property

Escape Coastal Resort on Casey Key

9.8/10 Exceptional! (287 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Sarasota (SRQ)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,156, price is now $933 per person
$933
per person
found 1 day ago
Property excellently maintained. Beautiful landscaping. Great amenities, they've thought of everything. Rooms, public spaces and grounds were all nice and clean. We absolutely loved it!

Reviewed on Jul 20, 2026

Venice Beach Villas
3.0-star property

Venice Beach Villas

9.4/10 Exceptional! (487 reviews)

Sep 6 - Sep 13

7 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,140, price is now $971 per person
$971
per person
found 1 day ago
The room is so cozy and cute, very comfortable and right by downtown old Venice as well as Venice beach. Felt very central to all the places we wanted to see and visit, we loved it!

Reviewed on Jul 21, 2026

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Little Gasparilla Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
GullWing Beach Resort
3.5-star property

GullWing Beach Resort

9.4/10 Exceptional! (957 reviews)

Aug 28 - Aug 31

3 night stay

New York (NYC) to Fort Myers (RSW)

Delta • FirstClass

Fort Myers (RSW) to New York (NYC)

United • FirstClass
Price was $1,543, price is now $1,352 per person
$1,352
per person
found 12 hours ago

Casa Ybel Resort
2.5-star property

Casa Ybel Resort

8.8/10 Excellent! (379 reviews)

Aug 28 - Aug 31

3 night stay

New York (NYC) to Fort Myers (RSW)

Delta • FirstClass

Fort Myers (RSW) to New York (NYC)

United • FirstClass
Price was $1,676, price is now $1,436 per person
$1,436
per person
found 12 hours ago

Tween Waters Island Resort & Spa
3.0-star property

Tween Waters Island Resort & Spa

8.6/10 Excellent! (1,007 reviews)

Aug 28 - Aug 31

3 night stay

New York (NYC) to Fort Myers (RSW)

Delta • FirstClass

Fort Myers (RSW) to New York (NYC)

United • FirstClass
Price was $1,613, price is now $1,420 per person
$1,420
per person
found 12 hours ago
Clean room, Frindly staff!

Reviewed on Jul 21, 2026

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Little Gasparilla Island

When you plan to buy tickets for flights to Little Gasparilla Island, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

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Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Little Gasparilla Island flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Little Gasparilla Island Flights

Orbitz offers deeply discounted flights to Little Gasparilla Island, and we provide the resources to research your travel destination and plan your complete itinerary.

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Saving your frequent flyer miles for your flights to Little Gasparilla Island? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Little Gasparilla Island flights.

Frequently asked questions

Which airlines fly to Little Gasparilla Island?
With 20 airlines ready to help you get away to Little Gasparilla Island, finding the ideal flight will be easy. Lock in your airfare with one of these popular carriers that offer services to Southwest Florida Intl. Airport (RSW):

  • Air Canada - 12 flights to Little Gasparilla Island per month
  • EW Discover - 3 flights to Little Gasparilla Island per month
  • WestJet - 3 flights to Little Gasparilla Island per month

How much is a flight to Little Gasparilla Island?
Travelers from far and wide landed round-trip flight bargains ranging between $87 and $197 this week. Kicking off your journey from Portsmouth (PSM)? The lowest one-way tickets started at just $51.
How to book the cheapest flight to Little Gasparilla Island?
Picking up cheap flights to Little Gasparilla Island is as easy as booking with Orbitz. But if you'd love to make sure you're nabbing the best flight deals around, here are some suggestions to keep in mind:

  • Taking off from or arriving at other airports can be more affordable. Enter your preferred departure and arrival airports. Next, select the 'Nearby airports' function below to look through your options.
  • If you're flexible with your schedule, click on the 'Show flexible dates' option. It'll bring up flight deals for the days either side of your chosen departure. Fares often vary depending on what day it is.
  • Hit 'Show options' to filter your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • Book as soon as you know your travel dates. While it does happen now and then, airfares rarely get more affordable as your date of departure gets closer.
  • Bundle your hotels, flights and car rentals into a package deal and enjoy discounts. Save your hard-earned dollars for things that really excite you, like discovering every corner of Little Gasparilla Island.
  • Don't fly during peak seasons if you can. By steering clear of summer and school vacations, you can save plenty on your airfares.

What is the best time to book a flight to Little Gasparilla Island?
Generally speaking, January is the best month to purchase your plane ticket. This is followed by February and August. Bear this in mind while you browse for a cheap flight to Little Gasparilla Island.
What day of the week is the cheapest to book a flight to Little Gasparilla Island?
To land an incredible flight deal, book on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days to book flights to Little Gasparilla Island.
What is the cheapest day of the week to fly to Little Gasparilla Island?
You can grab cheap flights to Little Gasparilla Island by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is the next most affordable day, while Saturday has the most expensive ticket prices. Whether you prefer to stretch your travel budget or start your trip on whichever day is convenient, you'll always find a great deal with Orbitz.
What is the cheapest month to fly to Little Gasparilla Island?
To pick up cheap flights to Little Gasparilla Island, you should fly out in August. If saving money on your plane ticket is your main concern, Orbitz data has found that this is generally the best month to jet off. June is when fares are at their highest.
Which airlines allow free cancellation?
Flexibility is important, that's why Orbitz lets you search for airlines that won't hit you with a fee for amendments to your reservation. Fill out your departure and arrival points, then select "Filter by flexible change policies." We'll show you all the options that include free cancellation and no change fees.
What do I need for the flight to Little Gasparilla Island?
There is so much to sort out for any big trip, so it's great to get a little bit of help along the way. Here's a handy checklist to ensure that you're prepared for take off:

  • Make sure you've packed your travel documents and some identification. For international trips, you'll need your passport. When you book your seats, always use the same details that are indicated on your government-issued ID.
  • A properly packed carry-on bag is the key to a great flight experience. Given your flight to Little Gasparilla Island is no short hop, take some snacks and activities to keep you occupied. Something to read or listen to will help pass the time.
  • Air conditioning and high altitudes can create a cool environment. No matter what the weather is in Little Gasparilla Island, bring an extra layer along to keep warm while on the plane.

How do I get cheap first-class/business deals to Little Gasparilla Island?
Smart travelers have a way of finding first or business-class flights to Little Gasparilla Island without the hefty price tag. Be like them with these handy tips:

  • Flexibility doesn't just help with your yoga. Avoid locking in your travel dates so you can snap up cheaper airfares when a huge sale drops.
  • Find a low-cost carrier that has seats in business class. They usually come with extra space and a glass of Champagne — but without the premium price.
  • Take advantage of your airline's loyalty scheme and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.