$71 Cheap flight deals from Portland (PWM) to Anastasia Island (DAB)

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This Weekend's Flight Deals from Portland to Anastasia Island

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 23 - Wed, Dec 3
PWM
Portland Intl. Jetport
MCO
Orlando Intl.
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Nov 23 from Portland Intl. Jetport to Orlando Intl., returning Wed, Dec 3, priced at $256 found 2 days ago
Sun, Nov 23 - Wed, Nov 26
PWM
Portland Intl. Jetport
DAB
Daytona Beach Intl.
$301 Roundtrip, found 5 days ago
$301
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Nov 23 from Portland Intl. Jetport to Daytona Beach Intl., returning Wed, Nov 26, priced at $301 found 5 days ago

Airfares from $71 One Way, $140 Round Trip from Portland to Anastasia Island

Prices starting at $140 for return flights and $71 for one-way flights to Anastasia Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 6 - Mon, Dec 8
PWM
Portland
MCO
Orlando
$140 Roundtrip, just found
$140
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Dec 6 from Portland to Orlando, returning Mon, Dec 8, priced at $140 just found
Sat, Dec 6 - Fri, Dec 12
PWM
Portland
MCO
Orlando
$141 Roundtrip, just found
$141
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Dec 6 from Portland to Orlando, returning Fri, Dec 12, priced at $141 just found
Wed, Dec 10 - Wed, Dec 17
PWM
Portland
MCO
Orlando
$146 Roundtrip, found 6 hours ago
$146
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, Dec 10 from Portland to Orlando, returning Wed, Dec 17, priced at $146 found 6 hours ago
Wed, Jan 28 - Mon, Feb 2
PWM
Portland
MCO
Orlando
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Jan 28 from Portland to Orlando, returning Mon, Feb 2, priced at $147 found 3 hours ago
Tue, Feb 3 - Tue, Feb 10
PWM
Portland
MCO
Orlando
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Feb 3 from Portland to Orlando, returning Tue, Feb 10, priced at $183 just found

Anastasia Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.2/10 Very Good! (5,210 reviews)

Dec 19 - Dec 22

3 night stay

Portland (PWM) to Orlando (MCO)

Southwest Airlines • Non-stop • Coach

Orlando (MCO) to Portland (PWM)

Breeze Airways • Non-stop • Coach
Save 100% on your flight
Price was $889, price is now $395 per person
$395
per person
found 19 hours ago
I was able to check in at 3:00pm but i had to wait till 4:00 to get my key resulting in a long line just to retrieve my key to my room. The elevator was very slow and needs to be updated. The room was updated with zero rugs but the paint inside the bathroom left much to be desired and the bathroom light came on automatically which was a terrible inconvenience for the other person in the room as they got rudely woken up when i had to use the bathroom in the middle of the night. The ac was loud and kept going on and off and wouldnt stay on and the beds although comfy kept hitting my shin when i got in and out of bed because the mattress didnt fit the bed correctly. The breakfast was ok but no fresh juice or muffins was provided as advertised.

Reviewed on Nov 10, 2025

Meliá Orlando Celebration
4.0-star property

Meliá Orlando Celebration

8.6/10 Excellent! (1,541 reviews)

Dec 25 - Jan 2

8 night stay

Portland (PWM) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Portland (PWM)

Breeze Airways • Coach
Save 100% on your flight
Price was $2,163, price is now $1,037 per person
$1,037
per person
found 1 day ago
Room was spacious and clean. It was like having your own apartment. A full-kitchen, separate shower and bath, and a balcony in the bedroom. Very friendly and helpful staff. The hotel had plenty of social activities for guests and is a short distance from Disney, downtown Celebration, and many restaurants. The balcony doors were hard to open and there was weed smell in some of the hallways.

Reviewed on Nov 12, 2025

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

17.6/10 Exceptional! (1,082 reviews)

Dec 25 - Jan 2

8 night stay

Portland (PWM) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Portland (PWM)

Breeze Airways • Coach
Save 100% on your flight
Price was $2,082, price is now $1,024 per person
$1,024
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

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More About Flying To Anastasia Island from Portland

Route Information for Flights from Portland to Anastasia Island

Origin Airport IATA Code
PWM
Destination Airport IATA Code
DAB
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Portland to Anastasia Island

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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.