$72 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.

Sat, Jan 3 - Mon, Jan 12
PWM
Portland Intl. Jetport
MCO
Orlando Intl.
$273 Roundtrip, just found
$273
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Jan 3 from Portland Intl. Jetport to Orlando Intl., returning Mon, Jan 12, priced at $273 just found
Sat, Jan 3 - Sat, Jan 17
PWM
Portland Intl. Jetport
DAB
Daytona Beach Intl.
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jan 3 from Portland Intl. Jetport to Daytona Beach Intl., returning Sat, Jan 17, priced at $408 found 1 day ago

Airfares from $72 One Way, $142 Round Trip from Portland to Anastasia Island

Prices starting at $142 for return flights and $72 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, Jan 24 - Wed, Feb 4
PWM
Portland
MCO
Orlando
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Jan 24 from Portland to Orlando, returning Wed, Feb 4, priced at $142 found 1 day ago
Sat, Jan 24 - Sat, Jan 31
PWM
Portland
MCO
Orlando
$143 Roundtrip, found 6 hours ago
$143
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Jan 24 from Portland to Orlando, returning Sat, Jan 31, priced at $143 found 6 hours ago
Sat, Jan 24 - Mon, Jan 26
PWM
Portland
MCO
Orlando
$144 Roundtrip, found 17 hours ago
$144
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Sat, Jan 24 from Portland to Orlando, returning Mon, Jan 26, priced at $144 found 17 hours ago
Wed, Feb 4 - Wed, Feb 11
PWM
Portland
MCO
Orlando
$161 Roundtrip, found 15 hours ago
$161
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Wed, Feb 4 from Portland to Orlando, returning Wed, Feb 11, priced at $161 found 15 hours ago
Sat, Jan 31 - Sat, Feb 7
PWM
Portland
MCO
Orlando
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 31 from Portland to Orlando, returning Sat, Feb 7, priced at $176 found 1 day ago

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! (5,145 reviews)

Feb 11 - Feb 14

3 night stay

Portland (PWM) to Orlando (MCO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $823, price is now $383 per person
$383
per person
found 1 day ago
Henry, front desk clerk, was exceptional with checking us in.

Reviewed on Dec 27, 2025

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.8/10 Excellent! (500 reviews)

Feb 24 - Feb 28

4 night stay

Portland (PWM) to Orlando (MCO)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,669, price is now $801 per person
$801
per person
found 1 day ago
Sue behind the bar was amazing. Hotel is a little dated and could use a new external color scheme. Rooms were modernized and mostly clean (sofa needs vacuumed) We had a great time and made use of all the pool areas and took advantage of happy hour every day. It is a bit of a walk from the main part of the resort to the beach so keep that in mind. Great place for family relaxing

Reviewed on Oct 5, 2025

Amelia by the South
4.0-star property

Amelia by the South

No reviews

Feb 16 - Feb 20

4 night stay

Portland (PWM) to Jacksonville (JAX)

American Airlines • Non-stop • Coach

Jacksonville (JAX) to Portland (PWM)

Delta • Non-stop • Coach
Price was $5,596, price is now $3,220 per person
$3,220
per person
found 1 day ago
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Anastasia Island packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,482 reviews)

Feb 22 - Feb 27

5 night stay

Portland (PWM) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,068, price is now $699 per person
$699
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

Westgate Cocoa Beach Resort
4.0-star property

Westgate Cocoa Beach Resort

8.8/10 Excellent! (500 reviews)

Feb 22 - Feb 27

5 night stay

Portland (PWM) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,280, price is now $1,377 per person
$1,377
per person
found 1 day ago
Sue behind the bar was amazing. Hotel is a little dated and could use a new external color scheme. Rooms were modernized and mostly clean (sofa needs vacuumed) We had a great time and made use of all the pool areas and took advantage of happy hour every day. It is a bit of a walk from the main part of the resort to the beach so keep that in mind. Great place for family relaxing

Reviewed on Oct 5, 2025

Meliá Orlando Celebration
4.0-star property

Meliá Orlando Celebration

8.6/10 Excellent! (1,549 reviews)

Feb 22 - Feb 27

5 night stay

Portland (PWM) to Orlando (MCO)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,208, price is now $801 per person
$801
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

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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.