$72 Cheap flight deals from Portland (PDX) 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 16 - Thu, Nov 20
PDX
Portland Intl.
MCO
Orlando Intl.
$419 Roundtrip, just found
$419
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Nov 16 from Portland Intl. to Orlando Intl., returning Thu, Nov 20, priced at $419 just found
Fri, Nov 14 - Tue, Nov 18
PDX
Portland Intl.
JAX
Jacksonville Intl.
$947 Roundtrip, found 2 days ago
$947
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Nov 14 from Portland Intl. to Jacksonville Intl., returning Tue, Nov 18, priced at $947 found 2 days ago

Airfares from $72 One Way, $144 Round Trip from Portland to Anastasia Island

Prices starting at $144 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.

Thu, Dec 4 - Fri, Dec 12
PDX
Portland
MCO
Orlando
$144 Roundtrip, found 16 hours ago
$144
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Portland to Orlando, returning Fri, Dec 12, priced at $144 found 16 hours ago
Thu, Dec 4 - Fri, Dec 5
PDX
Portland
MCO
Orlando
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 4 from Portland to Orlando, returning Fri, Dec 5, priced at $179 found 3 days ago
Sun, Jan 11 - Thu, Jan 15
PDX
Portland
MCO
Orlando
$179 Roundtrip, found 13 hours ago
$179
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sun, Jan 11 from Portland to Orlando, returning Thu, Jan 15, priced at $179 found 13 hours ago
Mon, Mar 9 - Tue, Mar 17
PDX
Portland
MCO
Orlando
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Delta flight, departing Mon, Mar 9 from Portland to Orlando, returning Tue, Mar 17, priced at $197 found 6 hours ago
Tue, Apr 7 - Fri, Apr 17
PDX
Portland
MCO
Orlando
$259 Roundtrip, found 4 hours ago
$259
Roundtrip
found 4 hours ago
Select United flight, departing Tue, Apr 7 from Portland to Orlando, returning Fri, Apr 17, priced at $259 found 4 hours ago

Anastasia Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kapp and Kappy B&B
3.5-star property

Kapp and Kappy B&B

9.8/10 Exceptional! (123 reviews)

Dec 30 - Jan 6

7 night stay

Portland (PDX) to Orlando (MCO)

Delta • Non-stop • Coach

Orlando (MCO) to Portland (PDX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $986, price is now $655 per person
$655
per person
found 1 day ago
We absolutely loved it. Amazing owners and outstanding hospitality. We will definitely be back.

Reviewed on Dec 11, 2022

Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (1,002 reviews)

Dec 30 - Jan 6

7 night stay

Portland (PDX) to Orlando (MCO)

Delta • Non-stop • Coach

Orlando (MCO) to Portland (PDX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,709, price is now $920 per person
$920
per person
found 1 day ago
The place is very nice! However, the washer did not work.

Reviewed on Oct 31, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9/10 Wonderful! (1,003 reviews)

Dec 12 - Dec 16

4 night stay

Portland (PDX) to Orlando (MCO)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,216, price is now $842 per person
$842
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

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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
PDX
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.