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Florida Keys

$100+ Cheap flights from Portland, ME (PWM) to Florida Keys

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
abr. 27 — may. 41
dom. 4/27
dom. 5/4
1 adult, Economy
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Cheap flight deals from Portland to Florida Keys

Keep the following information in mind while searching for Portland to Florida Keys flight deals. Data was last updated abril 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$541
Provider with most accurate pricing for Portland-Miami flight deals.
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Provider most trusted by Cheapflights users for Portland-Miami flights.
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From Portland to Florida Keys
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One-way flight from Portland to Florida Keys
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Highest demand for flights based on searches. 5% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Portland to Florida Keys

Cheapest flights from Portland to Florida Keys
Explore the most affordable flight options available from Portland to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 22, 2025.

This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/242:05 pmPWM - MIA
1 stop6h 09mAmerican Airlines
mar. 5/277:20 amMIA - PWM
1 stop7h 52mAmerican Airlines
Deal found 4/21$208
This JetBlue deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/133:35 pmPWM - MIA
1 stop8h 38mJetBlue
vie. 5/167:00 amMIA - PWM
1 stop7h 40mJetBlue
Deal found 4/22$215
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/132:30 pmPWM - MIA
1 stop8h 49mDelta
sáb. 5/177:15 amMIA - PWM
1 stop6h 35mDelta
Deal found 4/22$217
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/45:40 amPWM - MIA
2 stops10h 31mUnited Airlines
vie. 6/65:19 pmMIA - PWM
1 stop6h 08mUnited Airlines
Deal found 4/22$280
This American Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/107:35 amPWM - EYW
1 stop6h 14mAmerican Airlines
jue. 5/153:17 pmEYW - PWM
1 stop7h 49mAmerican Airlines
Deal found 4/21$294
This Southwest deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/132:20 pmPWM - MIA
1 stop7h 35mSouthwest
vie. 5/162:50 pmMIA - PWM
2 stops8h 30mSouthwest
Deal found 4/22$333
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/35:30 amPWM - EYW
1 stop7h 26mDelta
lun. 6/96:29 pmEYW - PWM
1 stop5h 57mDelta
Deal found 4/21$364
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/66:00 amPWM - EYW
1 stop7h 03mUnited Airlines
sáb. 5/108:45 amEYW - PWM
2 stops15h 14mUnited Airlines
Deal found 4/21$453
This Mytrip deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/512:40 pmPWM - MIA
2 stops22h 09mMultiple Airlines
jue. 6/1210:11 amMIA - PWM
3 stops27h 56mMultiple Airlines
Deal found 4/21$497

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Florida Keys that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 22, 2025.
Use the filters below to find and compare flights from Portland to Florida Keys that are best for you.

Fly from

Portland

Fly to

Florida Keys

Route

Depart

Return

Price

PortlandMiami

PWM - MIA

PWMMIA

Portland

sáb. 5/24

2:05 pm-8:14 pm

1 stop6h 09m

Miami

mar. 5/27

7:20 am-3:12 pm

1 stop7h 52m

$208

PortlandMiami

PWM - MIA

PWMMIA

Portland

mar. 5/13

3:35 pm-12:13 am

1 stop8h 38m

Miami

vie. 5/16

7:00 am-2:40 pm

1 stop7h 40m

$215

PortlandMiami

PWM - MIA

PWMMIA

Portland

mar. 5/13

2:30 pm-11:19 pm

1 stop8h 49m

Miami

sáb. 5/17

7:15 am-1:50 pm

1 stop6h 35m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

mié. 6/4

5:40 am-4:11 pm

2 stops10h 31m

Miami

vie. 6/6

5:19 pm-11:27 pm

1 stop6h 08m

$280

PortlandKey West

PWM - EYW

PWMEYW

Portland

sáb. 5/10

7:35 am-1:49 pm

1 stop6h 14m

Key West

jue. 5/15

3:17 pm-11:06 pm

1 stop7h 49m

$294

PortlandMiami

PWM - MIA

PWMMIA

Portland

mar. 5/13

2:20 pm-9:55 pm

1 stop7h 35m

Miami

vie. 5/16

2:50 pm-11:20 pm

2 stops8h 30m

$333

PortlandKey West

PWM - EYW

PWMEYW

Portland

mar. 6/3

5:30 am-12:56 pm

1 stop7h 26m

Key West

lun. 6/9

6:29 pm-12:26 am

1 stop5h 57m

$364

PortlandKey West

PWM - EYW

PWMEYW

Portland

mar. 5/6

6:00 am-1:03 pm

1 stop7h 03m

Key West

sáb. 5/10

8:45 am-11:59 pm

2 stops15h 14m

$453

PortlandMiami

PWM - MIA

PWMMIA

Portland

jue. 6/5

12:40 pm-10:49 am

2 stops22h 09m

Miami

jue. 6/12

10:11 am-2:07 pm

3 stops27h 56m

$497

PortlandMiami

PWM - MIA

PWMMIA

Portland

vie. 7/4

7:02 am-12:21 pm

1 stop5h 19m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 17 results
1
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Best time to book a flight from Portland to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Florida Keys

What is the cheapest month to book a flight from Portland, Maine to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $328). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $493). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PWM to EOA?

Find hourly flight availability from Portland to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 22, 2025.

When flying from Portland, Maine to Florida Keys, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated abril 22, 2025.
To help decide which airline to fly from Portland to Florida Keys, see what other customers have to say about Southwest, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Crew

8.6

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

Related info for your journey

Find useful and relevant information for your journey from Portland to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Florida Keys?

    For a flight from Portland to Florida Keys, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city.

  • What are the cheapest airlines to fly from Portland, Maine to Florida Keys one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Florida Keys are American Airlines ($100), Delta ($109), and United Airlines ($154).

  • Can I find deals for flights from Portland to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Portland to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Florida Keys.

  • Can I find deals for business class flights from Portland to Florida Keys?

    Yes. Cheapflights offers flight deals from Portland to Florida Keys by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Florida Keys (average of $328). Flying from Portland, Maine to Florida Keys in March is currently the most expensive (average of $493). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 3 airlines flying from Portland to Florida Keys

Discover the top 3 airlines that operate flights from Portland to Florida Keys. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$385FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$423FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$588FlexibilityNo cancel feeOn-time69%

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