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Find cheap flights from Portland to Florida Keys from $103

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Florida Keys departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 7/11
Thu 7/18

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Best Florida Keys Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Miami
Miami1 stop$199
Key West
Key West1 stop$198

Good to know

Low season

July

High season

February

Cheapest flight

$103
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Portland to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Portland to Florida Keys?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Florida Keys from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Florida Keys?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Florida Keys with an airline and back to Portland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Florida Keys?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Florida Keys from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Portland to Florida Keys

Need help choosing which airline to fly with from Portland to Florida Keys? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10277 reviews
7.4Food
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

2.0 MediocreNairan, May 2024JFK - FLL
Read more about Delta reviews

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

Did not wait long for wheelchair and attendant to arrive after checking in. Wheeled down to plane Was greeted with a smile when entering the plane Choice of snacks was very limited to 2 items. Seats are uncomfortable. My butt was sore after the 1st hour of flying. Needs better cushioning at seats.

Did not wait long for wheelchair and attendant to arrive after checking in. Wheeled down to plane Was greeted with a smile when entering the plane Choice of snacks was very limited to 2 items.

The entertainment wasn’t playing in the app or online.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

Flight was delayed due to the late arrival of the catering truck, which is quite unacceptable. There was a beverage service, but no pretzel, or cookie, or nuts were served in coach.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

Use planes with TVs on flights over 4 hours. The free entertainment was a cheap in between solution for a very long flight that you don't even bother providing meals or decent snacks.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

It was a good flight. Of course it was full, but it went well.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

We are gluten free, there were not any available complimentary gluten free options.

Flight delayed 3 times. We were directed to go to a gate across from our gate. The plane wasn't there yet so we had to wait for it to arrive, then deplane everyone and then wait again for the plane to be cleaned. After 45 minuites we were allowed on the plane. The first plane had mechanical issues. The 2nd plane must have had bathroom issues because we did not have any food service whatsoever. No snack or beverage. That made for a long time not to have anything considering that we had just made it to the original gate and we had no time to stop to get food or a drink. Then we didn't want to leave the gate to get food because we wouldn't know how much longer the delay would be. Then the next gate change. Had we been told that the total time would have been aprox 45 min later we would have left to get food and a beverage. We had to wait again for the okay to the pilot to take off so we were on the runway for another 20 min. Overall, we were delayed over 2 hours which felt like 4 hours.

Lots of weather delays that were poorly communicated and managed. I get there are weather delays but they didn’t make it clear what was happening or comfortable on the plane

Book cheap flights from Portland to Florida Keys

Recent round-trip flight deals

8/31Sat
1 stopAmerican Airlines
8h 18mPWM-EYW
9/4Wed
1 stopAmerican Airlines
5h 39mEYW-PWM
$198
7/11Thu
1 stopFrontier
24h 25mPWM-MIA
7/16Tue
1 stopFrontier
7h 51mMIA-PWM
$199
9/24Tue
1 stopJetBlue
7h 25mPWM-MIA
9/27Fri
1 stopJetBlue
5h 29mMIA-PWM
$204
8/15Thu
2 stopsDelta
11h 06mPWM-EYW
8/19Mon
1 stopDelta
7h 30mEYW-PWM
$237
11/1Fri
1 stopDelta
16h 10mPWM-MIA
11/4Mon
1 stopDelta
27h 12mMIA-PWM
$265
7/9Tue
1 stopJetBlue
7h 53mPWM-MIA
7/16Tue
1 stopJetBlue
8h 39mMIA-PWM
$305
7/9Tue
1 stopUnited Airlines
8h 09mPWM-EYW
7/16Tue
1 stopUnited Airlines
5h 45mEYW-PWM
$403
7/10Wed
3 stops
33h 24mPWM-MIA
7/17Wed
2 stops
26h 59mMIA-PWM
$451
7/31Wed
3 stops
27h 51mPWM-MIA
8/8Thu
2 stops
16h 04mMIA-PWM
$460
10/16Wed
1 stopUnited Airlines
6h 18mPWM-MIA
10/25Fri
2 stopsUnited Airlines
18h 13mMIA-PWM
$492

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Recent one-way flight deals

7/4Thu
1 stopAmerican Airlines
5h 37mPWM-MIA
$103
7/9Tue
1 stopUnited Airlines
8h 27mPWM-MIA
$134
7/9Tue
1 stopJetBlue
7h 53mPWM-MIA
$159
7/16Tue
1 stopDelta
7h 20mPWM-EYW
$163
7/12Fri
2 stops
26h 18mPWM-MIA
$163
6/29Sat
1 stopAmerican Airlines
6h 14mPWM-MIA
$164
7/16Tue
2 stopsAmerican Airlines
8h 42mPWM-EYW
$168
6/25Tue
1 stopFrontier
14h 17mPWM-MIA
$175
7/22Mon
1 stopUnited Airlines
8h 12mPWM-MIA
$228
7/8Mon
2 stopsDelta
8h 43mPWM-MIA
$487

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Last minute flights from Portland to Florida Keys

Last minute flight, train and bus deals

6/14Fri
multi-stopAmerican Airlines
8h 28mPWM-MIA
6/15Sat
multi-stopAmerican Airlines
5h 42mMIA-PWM
$594
6/14Fri
multi-stopAmerican Airlines
7h 23mPWM-MIA
6/15Sat
multi-stopAmerican Airlines
6h 22mMIA-PWM
$683
6/14Fri
multi-stop
25h 03mPWM-MIA
6/15Sat
multi-stop
23h 17mMIA-PWM
$785

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Portland - Florida Keys Flights

Departure:

Portland (PWM)United States

Return flight deals:

Florida Keys - Portland

Cabin classes:

$253
$789
$268
$72