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Cheap flights from Portland, Maine to Florida Keys from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Florida Keys departing on 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Portland, Maine to Florida Keys

Cheap round-trip flights

Southwest Logo
12:00 pm - 8:35 pmPWM-MIA
8h 35m1 stop
Southwest Logo
1:55 pm - 7:55 pmMIA-PWM
6h 00m1 stop
$217Southwest
Find Deal
Tue, Oct 28 - Wed, Oct 29
Southwest Logo
12:00 pm - 8:35 pmPWM-MIA
8h 35m1 stop
Southwest Logo
6:55 am - 4:50 pmMIA-PWM
9h 55m2 stops
$222Southwest
Find Deal
Tue, Oct 28 - Wed, Oct 29
American Airlines Logo
7:05 am - 4:16 pmPWM-MIA
9h 11m1 stop
American Airlines Logo
10:02 am - 8:14 pmMIA-PWM
10h 12m1 stop
$223American Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
United Airlines Logo
8:00 am - 2:17 pmPWM-MIA
6h 17m1 stop
United Airlines Logo
1:28 pm - 11:59 pmMIA-PWM
10h 31m2 stops
$232United Airlines
Find Deal
Tue, Sep 30 - Tue, Oct 7
United Airlines Logo
3:12 pm - 10:20 pmPWM-MIA
7h 08m1 stop
United Airlines Logo
5:10 pm - 11:21 pmMIA-PWM
6h 11m1 stop
$237United Airlines
Find Deal
Sat, Feb 7 - Sat, Feb 14
Delta Logo
2:34 pm - 4:57 pmPWM-MIA
26h 23m1 stop
Delta Logo
3:46 pm - 10:42 pmMIA-PWM
6h 56m1 stop
$250Delta
Find Deal
Fri, Dec 19 - Wed, Dec 24
American Airlines Logo
2:24 pm - 11:11 pmPWM-MIA
8h 47m1 stop
American Airlines Logo
6:55 am - 12:05 pmMIA-PWM
5h 10m1 stop
$258American Airlines
Find Deal
Wed, Jan 28 - Sun, Feb 1
Delta Logo
6:00 am - 12:22 pmPWM-MIA
6h 22m1 stop
Delta Logo
7:59 pm - 11:54 pmMIA-PWM
27h 55m1 stop
$260Delta
Find Deal
Sat, Nov 15 - Sat, Nov 22
Multiple Airlines Logo
3:15 pm - 9:17 amPWM-EYW
18h 02m2 stops
Multiple Airlines Logo
3:07 pm - 5:38 pmEYW-PWM
26h 31m1 stop
$338Multiple Airlines
Find Deal
Sun, Nov 9 - Fri, Nov 14
Multiple Airlines Logo
3:15 pm - 9:20 amPWM-EYW
18h 05m1 stop
Multiple Airlines Logo
8:55 am - 9:06 amEYW-PWM
24h 11m1 stop
$376Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9

American Airlines flights from Portland, Maine to Florida Keys

Our best American Airlines deals on Portland, Maine to Florida Keys flight tickets
American Airlines
Sep 30
PWM7:05 amPortland
9h 11m
1 stop
MIA4:16 pmMiami
Oct 7
MIA10:02 amMiami
10h 12m
1 stop
PWM8:14 pmPortland
$223
Find similar
American Airlines
Jan 28
PWM2:24 pmPortland
8h 47m
1 stop
MIA11:11 pmMiami
Feb 1
MIA6:55 amMiami
5h 10m
1 stop
PWM12:05 pmPortland
$258
Find similar
American Airlines
Jan 28
PWM1:22 pmPortland
7h 16m
2 stops
MIA8:38 pmMiami
Feb 1
MIA6:55 amMiami
5h 10m
1 stop
PWM12:05 pmPortland
$263
Find similar

United Airlines flights from Portland, Maine to Florida Keys

Our best United Airlines deals on Portland, Maine to Florida Keys flight tickets
United Airlines
Sep 30
PWM8:00 amPortland
6h 17m
1 stop
MIA2:17 pmMiami
Oct 7
MIA1:28 pmMiami
10h 31m
2 stops
PWM11:59 pmPortland
$232
Find similar
United Airlines
Feb 7
PWM3:12 pmPortland
7h 08m
1 stop
MIA10:20 pmMiami
Feb 14
MIA5:10 pmMiami
6h 11m
1 stop
PWM11:21 pmPortland
$237
Find similar
United Airlines
Feb 7
PWM3:12 pmPortland
8h 47m
1 stop
MIA11:59 pmMiami
Feb 13
MIA12:15 pmMiami
11h 06m
2 stops
PWM11:21 pmPortland
$242
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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, momondo users made 832,500 searches. Data last updated September 18, 2025.
Use the filters below to find and compare flights from Portland, Maine to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 10/28

12:00 pm-8:35 pm

1 stop8h 35m

Miami

Wed 10/29

1:55 pm-7:55 pm

1 stop6h 00m

$217

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 10/28

12:00 pm-8:35 pm

1 stop8h 35m

Miami

Wed 10/29

6:55 am-4:50 pm

2 stops9h 55m

$222

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 9/30

7:05 am-4:16 pm

1 stop9h 11m

Miami

Tue 10/7

10:02 am-8:14 pm

1 stop10h 12m

$223

PortlandMiami

PWM - MIA

PWMMIA

Portland

Tue 9/30

8:00 am-2:17 pm

1 stop6h 17m

Miami

Tue 10/7

1:28 pm-11:59 pm

2 stops10h 31m

$232

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 2/7

3:12 pm-10:20 pm

1 stop7h 08m

Miami

Sat 2/14

5:10 pm-11:21 pm

1 stop6h 11m

$237

PortlandMiami

PWM - MIA

PWMMIA

Portland

Fri 12/19

2:34 pm-4:57 pm

1 stop26h 23m

Miami

Wed 12/24

3:46 pm-10:42 pm

1 stop6h 56m

$250

PortlandMiami

PWM - MIA

PWMMIA

Portland

Wed 1/28

2:24 pm-11:11 pm

1 stop8h 47m

Miami

Sun 2/1

6:55 am-12:05 pm

1 stop5h 10m

$258

PortlandMiami

PWM - MIA

PWMMIA

Portland

Sat 11/15

6:00 am-12:22 pm

1 stop6h 22m

Miami

Sat 11/22

7:59 pm-11:54 pm

1 stop27h 55m

$260

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 11/9

3:15 pm-9:17 am

2 stops18h 02m

Key West

Fri 11/14

3:07 pm-5:38 pm

1 stop26h 31m

$338

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 11/6

3:15 pm-9:20 am

1 stop18h 05m

Key West

Sun 11/9

8:55 am-9:06 am

1 stop24h 11m

$376

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Florida Keys from

How to get the cheapest flight ticket from Portland, Maine to Florida Keys

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Florida Keys?

The month of August is another great option to travel to Florida Keys, with average flight prices from Portland, Maine averaging around $296.

What is the cheapest day to depart on your flight to Florida Keys?

The cheapest day to depart from Portland, Maine to Florida Keys is on a Wednesday when prices can be found for as low as $379. The most expensive day to fly to Florida Keys is Monday, with ticket prices averaging around $544.

What is the cheapest time of day to depart on your flight to Florida Keys?

According to our data, the cheapest time of day to fly to Florida Keys is at noon. momondo users have found flights departing from Portland, Maine to Florida Keys at noon for as low as $438. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights in the morning are often more expensive with an average ticket price of $486.

How far in advance should I book a flight to Florida Keys?

You are more likely to see cheaper flights to Florida Keys from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida Keys for around $410 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida Keys from Portland, Maine for as low as $312 on momondo.

Can stopping save me money on Portland, Maine to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between Portland, Maine to Florida Keys.

Cheap Portland, Maine to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Florida Keys

Direct flights

None
There are no direct flights from Portland, Maine to Florida Keys. There are no popular flight routes from Portland, Maine to Florida Keys.
Search flight deals

  • When did momondo last update prices for flights from Portland Airport to Florida Keys?

    Prices for flights from Portland Airport to Florida Keys are updated daily.

  • How many operators does momondo search for flights from Portland Airport to Florida Keys?

  • How old do you have to be to fly from Portland Airport to Florida Keys?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Florida Keys.

  • What documentation or ID do you need to fly to Florida Keys?

    The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Portland, Maine to Florida Keys?

Best airlines flying from Portland, Maine to Florida Keys

Compare and see reviews for airlines that fly from Portland, Maine to Florida Keys with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $268Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $293Free CancellationRating
7.9
7,964 reviews
Search Delta flights
United AirlinesPriceFrom $372Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Florida Keys?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Florida Keys. momondo saves you time and could save you money on your trip.

Can I find flights from Portland to Florida Keys with flexible booking policies on momondo?

momondo does allow users to show only those flights to Florida Keys from Portland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Portland to Florida Keys?

momondo provides multiple filters to help you find the best flight to Florida Keys from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Portland to Florida Keys right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Florida Keys, momondo offers a useful price alert feature which will track prices for flights to Florida Keys from Portland and alert you when they change.

An easier way to manage your Florida Keys trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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