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Sat, May 2 - Mon, May 4
PWM
Portland Intl. Jetport
MCO
Orlando Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, May 2 from Portland Intl. Jetport to Orlando Intl., returning Mon, May 4, priced at $257 found 2 days ago
Sun, May 3 - Sun, May 10
PWM
Portland Intl. Jetport
JAX
Jacksonville Intl.
$606 Roundtrip, found 1 day ago
$606
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, May 3 from Portland Intl. Jetport to Jacksonville Intl., returning Sun, May 10, priced at $606 found 1 day ago
Wed, Aug 26 - Mon, Aug 31
PWM
Portland
MCO
Orlando
$156 Roundtrip, found 6 days ago
$156
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Aug 26 from Portland to Orlando, returning Mon, Aug 31, priced at $156 found 6 days ago
Wed, Aug 26 - Sat, Aug 29
PWM
Portland
MCO
Orlando
$157 Roundtrip, found 20 hours ago
$157
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Portland to Orlando, returning Sat, Aug 29, priced at $157 found 20 hours ago
Wed, Aug 26 - Mon, Aug 31
PWM
Portland
MCO
Orlando
$165 Roundtrip, found 6 days ago
$165
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Portland to Orlando, returning Mon, Aug 31, priced at $165 found 6 days ago
Wed, May 27 - Fri, May 29
PWM
Portland
MCO
Orlando
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, May 27 from Portland to Orlando, returning Fri, May 29, priced at $179 found 6 days ago
Sat, Jan 16 - Sat, Jan 23
PWM
Portland
MCO
Orlando
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 16 from Portland to Orlando, returning Sat, Jan 23, priced at $217 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

9/10 Wonderful! (3,511 reviews)

May 27 - Jun 3

7 night stay

Portland (PWM) to Orlando (MCO)

Breeze Airways • Coach

Orlando (MCO) to Portland (PWM)

American Airlines • Coach
Save 100% on your flight
Price was $734, price is now $417 per person
$417
per person
found 8 hours ago
Very clean no roaches or beg bugs only thing I seen was a ant staff was very helpful Perfect for a week stay

Reviewed on Apr 15, 2026

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8.2/10 Very Good! (1,633 reviews)

May 27 - Jun 3

7 night stay

Portland (PWM) to Orlando (MCO)

Breeze Airways • Coach

Orlando (MCO) to Portland (PWM)

American Airlines • Coach
Save 100% on your flight
Price was $897, price is now $427 per person
$427
per person
found 8 hours ago
Everything was good

Reviewed on Apr 15, 2026

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,254 reviews)

May 27 - Jun 3

7 night stay

Portland (PWM) to Orlando (MCO)

Breeze Airways • Coach

Orlando (MCO) to Portland (PWM)

American Airlines • Coach
Save 100% on your flight
Price was $977, price is now $494 per person
$494
per person
found 8 hours ago
Great location to everything as far as food, Walmart, attractions etc. Beds were horrible and the parking at night. The water park only has 2 water slides and a small wave pool. It's a joke to charge guest to come in.

Reviewed on Apr 5, 2026

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Frequently asked questions

Are there non-stop flights from Portland to Gainesville?
Yes, Frontier Airlines flies straight from Portland to Gainesville, so you'll be touching down and starting your awesome adventure in next to no time.
What is the shortest flight from Portland to Gainesville?
From Portland, the exciting sights and sounds of Gainesville are at least 3 hours and 51 minutes away. Book your favorite seat, or maybe even one with more legroom, and fly to your destination in pure comfort.
What airlines fly from Portland to Gainesville most frequently?
If you're looking for the airline that offers the most flights from Portland to Gainesville, Frontier Airlines is the top pick. This popular carrier operates 8 flights on this route each month.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.