Cheap flights from PWM to EYW (Portland Intl. Jetport to Key West Intl.)

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Cheap Flights from PWM to EYW starting at $339 One Way, $291 Round Trip

Prices starting at $291 for return flights and $339 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Dec 9 - Wed, Dec 16
PWM
Portland
EYW
Key West
$291 Roundtrip, found 3 days ago
$291
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Dec 9 from Portland to Key West, returning Wed, Dec 16, priced at $291 found 3 days ago
Wed, Oct 28 - Wed, Nov 4
PWM
Portland
EYW
Key West
$291 Roundtrip, found 3 days ago
$291
Roundtrip
found 3 days ago
Select United flight, departing Wed, Oct 28 from Portland to Key West, returning Wed, Nov 4, priced at $291 found 3 days ago
Sat, Aug 29 - Sat, Sep 5
PWM
Portland
EYW
Key West
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Aug 29 from Portland to Key West, returning Sat, Sep 5, priced at $298 found 5 days ago
Tue, Dec 8 - Tue, Dec 15
PWM
Portland
EYW
Key West
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 8 from Portland to Key West, returning Tue, Dec 15, priced at $301 found 1 day ago
Wed, Dec 9 - Wed, Dec 16
PWM
Portland
EYW
Key West
$311 Roundtrip, found 3 days ago
$311
Roundtrip
found 3 days ago
Select United flight, departing Wed, Dec 9 from Portland to Key West, returning Wed, Dec 16, priced at $311 found 3 days ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$287 nightly
The price is $323 total per night from Aug 24 to Aug 25
$323 total
Aug 24 - Aug 25
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,207 reviews)
"Enjoyed!"

Reviewed on Jul 24, 2026

Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$161 nightly
The price is $181 total per night from Aug 12 to Aug 13
$181 total
Aug 12 - Aug 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,441 reviews)
"Great location!"

Reviewed on Jul 23, 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$165 nightly
The price is $186 total per night from Aug 9 to Aug 10
$186 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
DoubleTree Resort by Hilton Grand Key - Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$210 nightly
The price is $237 total per night from Aug 18 to Aug 19
$237 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$202 nightly
The price is $227 total per night from Aug 17 to Aug 18
$227 total
Aug 17 - Aug 18
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,368 reviews)
"Clean, convenient and beautiful property. The staff was great and helpful, tell John B I said what’s up!!!"

Reviewed on Jul 24, 2026

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
$152 nightly
The price is $171 total per night from Aug 23 to Aug 24
$171 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the pool and ...
Hilton Garden Inn Key West / The Keys Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$165 nightly
The price is $186 total per night from Aug 9 to Aug 10
$186 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$161 nightly
The price is $181 total per night from Aug 12 to Aug 13
$181 total
Aug 12 - Aug 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,441 reviews)
"Great location!"

Reviewed on Jul 23, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$171 nightly
The price is $192 total per night from Aug 24 to Aug 25
$192 total
Aug 24 - Aug 25
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
Eden House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Key West Hotels

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$155 nightly
The price is $175 total per night from Aug 23 to Aug 24
$175 total
Aug 23 - Aug 24
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,370 reviews)
"0000000"

Reviewed on Jul 24, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$120 nightly
The price is $135 total per night from Jul 29 to Jul 30
$135 total
Jul 29 - Jul 30
Total with taxes and fees
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,001 reviews)
"Fair and clean room, but security is an issue due to doors on the street face (easy access to anyone). Limited parking spot"

Reviewed on Jul 21, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$124 nightly
The price is $137 total per night from Jul 27 to Jul 28
$137 total
Jul 27 - Jul 28
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,064 reviews)
"Loved everything about our stay here — the warm welcome and welcome beer, super kind and helpful staff, most delicious breakfast, our room was super clean and cute with nice balcony. The location can’t be beat and we were sad to leave. Thank you for all!!"

Reviewed on Jul 24, 2026

Duval House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$210 nightly
The price is $237 total per night from Aug 18 to Aug 19
$237 total
Aug 18 - Aug 19
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$171 nightly
The price is $192 total per night from Aug 23 to Aug 24
$192 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (2,574 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
"We had a wonderful stay at Blue Flamingo. Our rooms were clean and well stocked with a Keurig and pods and clean towels. Shampoo, conditioner, hand soap, body soap, and lotion dispensers. The grounds were great! Three pools, three bars, and food trucks. The food choices were very limited after 4pm. ..."

Reviewed on Jul 24, 2026

Blue Flamingo Resort Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$193 nightly
The price is $217 total per night from Aug 2 to Aug 3
$217 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,843 reviews)
"The beginning of this trip was absolutely awful. After not receiving a check-in for my American Airlines flight, I called Expedia and was told our flight was confirmed to leave on July 17 at 6:00 a.m. and that I would need to check in at the airline desk. That should have been a red flag. When we ..."

Reviewed on Jul 23, 2026

Hilton Key West Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

PWM to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
PWM Address & GPS
Address:
1001 Westbrook Street
Portland ME, 04102
United States
IATA Code:
PWM
Longitude:
-70.310307
Latitude:
43.647492
Time Zone:
America/New_York
EYW Address & GPS
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA Code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from Portland Intl. Jetport to Key West Intl. Airport?
While you can't fly direct from Portland Intl. Jetport to EYW, there are a number of carriers that operate on this route with just a single stopover. Why not find out if the dates offered by American Airlines or United Airlines suit your travel plans? If they don't, you could always check out Delta Air Lines.
What is the shortest flight from Portland Intl. Jetport to Key West Intl. Airport?
The shortest flight time from Portland to Key West is around 5 hours and 20 minutes. Grab a refreshment from the drink trolley, hone your travel itinerary or get to know your neighbors — you'll have the time on this medium-haul journey.
How many hours flight from PWM to Key West Intl. Airport?
It usually takes around 5 hours and 26 minutes to get from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW). You'll be in your seat for quite some time, so consider taking some entertainment, like a novel or your travel journal.
What airlines have the most flights from Portland Intl. Jetport Airport (PWM) to EYW?
Do a little shopping, grab a quick meal, stretch your legs … Airport stopovers don't have to be boring! If you're heading from Portland to Key West, you won't be able to fly direct. Be prepared for at least one stopover somewhere.

Map To Nearby Hotels

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.

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