Latest deals
Insights
FAQs
Price Alerts

Cheap flights from New Windsor to Florida Keys from $123

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Florida Keys departing on 8/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from New Windsor to Florida Keys

Cheap round-trip flights

Logo
11:31 am - 12:13 pmSWF-MIA
24h 42m2 stops
Logo
7:01 pm - 2:11 pmMIA-SWF
19h 10m2 stops
$250
Find Deal
vie., oct. 24 - dom., oct. 26
Logo
11:31 am - 12:13 pmSWF-MIA
24h 42m2 stops
Logo
7:01 pm - 10:11 amMIA-SWF
15h 10m2 stops
$260
Find Deal
vie., oct. 17 - dom., oct. 19
Logo
7:12 pm - 2:54 pmSWF-EYW
19h 42m1 stop
Logo
8:55 am - 11:44 amEYW-SWF
26h 49m2 stops
$278
Find Deal
dom., sep. 7 - dom., sep. 14
Allegiant Air Logo
11:09 am - 9:37 pmSWF-EYW
10h 28m1 stop
Allegiant Air Logo
5:46 pm - 10:19 amEYW-SWF
16h 33m1 stop
$279Allegiant Air
Find Deal
dom., dic. 7 - sáb., dic. 13
Logo
5:36 pm - 6:39 pmSWF-MIA
25h 03m2 stops
Logo
9:29 pm - 4:46 pmMIA-SWF
19h 17m2 stops
$306
Find Deal
vie., ago. 22 - dom., ago. 24
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 11:56 amEYW-SWF
25h 54m1 stop
$333Breeze Airways
Find Deal
jue., ago. 21 - lun., ago. 25
Allegiant Air Logo
12:13 pm - 9:43 amSWF-EYW
21h 30m1 stop
Allegiant Air Logo
5:51 pm - 10:12 amEYW-SWF
16h 21m1 stop
$411Allegiant Air
Find Deal
jue., ago. 28 - dom., ago. 31
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 11:56 amEYW-SWF
25h 54m1 stop
$488Breeze Airways
Find Deal
jue., ago. 21 - lun., ago. 25
Allegiant Air Logo
12:13 pm - 9:43 amSWF-EYW
21h 30m1 stop
Allegiant Air Logo
5:51 pm - 10:12 amEYW-SWF
16h 21m1 stop
$509Allegiant Air
Find Deal
jue., ago. 21 - dom., ago. 24
Breeze Airways Logo
11:43 am - 11:52 amSWF-EYW
24h 09m1 stop
Breeze Airways Logo
8:55 am - 11:44 amEYW-SWF
26h 49m2 stops
$547Breeze Airways
Find Deal
dom., sep. 7 - jue., sep. 11

Allegiant Air flights from New Windsor to Florida Keys

Our best Allegiant Air deals on New Windsor to Florida Keys flight tickets
Allegiant Air
Dec 7
SWF11:09 amNew Windsor Stewart
10h 28m
1 stop
EYW9:37 pmKey West
Dec 13
EYW5:46 pmKey West
16h 33m
1 stop
SWF10:19 amNew Windsor Stewart
$279
Find similar
Allegiant Air
Aug 28
SWF12:13 pmNew Windsor Stewart
21h 30m
1 stop
EYW9:43 amKey West
Aug 31
EYW5:51 pmKey West
16h 21m
1 stop
SWF10:12 amNew Windsor Stewart
$411
Find similar
Allegiant Air
Aug 13
SWF7:06 pmNew Windsor Stewart
19h 04m
1 stop
EYW2:10 pmKey West
Aug 21
EYW3:12 pmKey West
19h 00m
1 stop
SWF10:12 amNew Windsor Stewart
$413
Find similar

Breeze Airways flights from New Windsor to Florida Keys

Our best Breeze Airways deals on New Windsor to Florida Keys flight tickets
Breeze Airways
Aug 21
SWF7:52 pmNew Windsor Stewart
17h 15m
1 stop
EYW1:07 pmKey West
Aug 25
EYW10:02 amKey West
25h 54m
1 stop
SWF11:56 amNew Windsor Stewart
$333
Find similar
Breeze Airways
Aug 25
SWF1:28 pmNew Windsor Stewart
19h 54m
2 stops
EYW9:22 amKey West
Aug 28
EYW10:02 amKey West
9h 10m
1 stop
SWF7:12 pmNew Windsor Stewart
$414
Find similar
Breeze Airways
Aug 14
SWF7:52 pmNew Windsor Stewart
17h 15m
1 stop
EYW1:07 pmKey West
Aug 18
EYW10:02 amKey West
25h 54m
1 stop
SWF11:56 amNew Windsor Stewart
$430
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor 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 agosto 11, 2025.
Use the filters below to find and compare flights from New Windsor to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 10/24

11:31 am-12:13 pm

2 stops24h 42m

Miami

dom. 10/26

7:01 pm-2:11 pm

2 stops19h 10m

$250

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 10/17

11:31 am-12:13 pm

2 stops24h 42m

Miami

dom. 10/19

7:01 pm-10:11 am

2 stops15h 10m

$260

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 9/7

7:12 pm-2:54 pm

1 stop19h 42m

Key West

dom. 9/14

8:55 am-11:44 am

2 stops26h 49m

$278

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 12/7

11:09 am-9:37 pm

1 stop10h 28m

Key West

sáb. 12/13

5:46 pm-10:19 am

1 stop16h 33m

$279

New WindsorMiami

SWF - MIA

SWFMIA

New Windsor Stewart

vie. 8/22

5:36 pm-6:39 pm

2 stops25h 03m

Miami

dom. 8/24

9:29 pm-4:46 pm

2 stops19h 17m

$306

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 8/21

7:52 pm-1:07 pm

1 stop17h 15m

Key West

lun. 8/25

10:02 am-11:56 am

1 stop25h 54m

$333

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 8/28

12:13 pm-9:43 am

1 stop21h 30m

Key West

dom. 8/31

5:51 pm-10:12 am

1 stop16h 21m

$411

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 8/21

7:52 pm-1:07 pm

1 stop17h 15m

Key West

lun. 8/25

10:02 am-11:56 am

1 stop25h 54m

$488

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

jue. 8/21

12:13 pm-9:43 am

1 stop21h 30m

Key West

dom. 8/24

5:51 pm-10:12 am

1 stop16h 21m

$509

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

dom. 9/7

11:43 am-11:52 am

1 stop24h 09m

Key West

jue. 9/11

8:55 am-11:44 am

2 stops26h 49m

$547

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Florida Keys from

How to get the cheapest flight ticket from New Windsor 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 day to depart on your flight to Florida Keys?

The cheapest day to depart from New Windsor to Florida Keys is on a Thursday when prices can be found for as low as $97. The most expensive day to fly to Florida Keys is Friday, with ticket prices averaging around $216.

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 in the evening. momondo users have found flights departing from New Windsor to Florida Keys in the evening for as low as $131. 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 afternoon are often more expensive with an average ticket price of $161.

Can stopping save me money on New Windsor to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between New Windsor to Florida Keys.

Cheap New Windsor to Florida Keys flight deals and tips

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

Best Price Found

$123

Fastest flight time

10h 05m

Direct flights

None

Airports in Florida Keys

2 airports
The best one-way flight to Florida Keys from New Windsor in the past 72 hours is $123. The best round-trip flight deal from New Windsor to Florida Keys found on momondo in the last 72 hours is $250.
The fastest flight from New Windsor to Florida Keys takes 10h 05m
There are no direct flights from New Windsor to Florida Keys. Popular non-direct routes for this connection are New Windsor Stewart Airport - Key West Airport and New Windsor Stewart Airport - Miami Airport.
There are 2 airports near Florida Keys: Key West (EYW), Miami (MIA)
Search flight deals

  • When did momondo last update prices for flights from New Windsor Stewart Airport to Florida Keys?

    Prices for flights from New Windsor Stewart Airport to Florida Keys are refreshed on a daily basis.

  • How many operators does momondo search for flights from New Windsor Stewart Airport to Florida Keys?

  • How old do you have to be to fly from New Windsor Stewart 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 New Windsor Stewart 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 New Windsor to Florida Keys?

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Florida Keys. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for New Windsor to Florida Keys flights to just show those with flexible booking policies.

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

Once you have performed a search for New Windsor to Florida Keys flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Florida Keys from New Windsor are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
sáb. 8/16
sáb. 8/23
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Florida Keys

Popular cities in Florida Keys

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $58
Flights to Los Angelesfrom $46
Flights to Miamifrom $61
Flights to Chicagofrom $47
Flights to Orlandofrom $61
Flights to Las Vegasfrom $15
Flights to San Franciscofrom $69
Flights to Washington, D.C.from $56
Flights to Bostonfrom $67
Flights to Atlantafrom $49
Flights to Dallasfrom $61
Flights to Seattlefrom $84