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Cheap flights from New Windsor to Key West from $126

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 Key West departing on 8/29. 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
1 adult, Economy, 0 bags

Find the cheapest flights from New Windsor to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Breeze Airways Logo
11:59 am - 11:39 am
EYW
-
SWF
23h 40m
1 stop
$196Breeze Airways
Sun, Aug 30 - Fri, Sep 25
Breeze Airways Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Breeze Airways Logo
12:59 pm - 11:39 am
EYW
-
SWF
22h 40m
2 stops
$208Breeze Airways
Sun, Aug 30 - Fri, Sep 25
Breeze Airways Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Breeze Airways Logo
12:07 pm - 11:08 am
EYW
-
SWF
23h 01m
1 stop
$217Breeze Airways
Thu, Aug 27 - Mon, Aug 31
Breeze Airways Logo
12:05 pm - 10:24 am
SWF
-
EYW
22h 19m
2 stops
Breeze Airways Logo
12:07 pm - 11:08 am
EYW
-
SWF
23h 01m
1 stop
$253Breeze Airways
Sat, Aug 29 - Mon, Aug 31
Breeze Airways Logo
12:05 pm - 11:25 am
SWF
-
EYW
23h 20m
2 stops
Breeze Airways Logo
12:07 pm - 11:08 am
EYW
-
SWF
23h 01m
1 stop
$259Breeze Airways
Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
12:05 pm - 10:24 am
SWF
-
EYW
22h 19m
2 stops
Multiple Airlines Logo
3:48 pm - 10:23 am
EYW
-
SWF
18h 35m
1 stop
$269Multiple Airlines
Sat, Aug 29 - Sat, Sep 5
Breeze Airways Logo
12:05 pm - 11:25 am
SWF
-
EYW
23h 20m
2 stops
Breeze Airways Logo
12:07 pm - 11:08 am
EYW
-
SWF
23h 01m
1 stop
$270Breeze Airways
Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
12:16 pm - 9:24 am
SWF
-
EYW
21h 08m
2 stops
Multiple Airlines Logo
6:11 pm - 10:31 am
EYW
-
SWF
16h 20m
1 stop
$272Multiple Airlines
Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
12:16 pm - 9:24 am
SWF
-
EYW
21h 08m
2 stops
Multiple Airlines Logo
6:11 pm - 10:31 am
EYW
-
SWF
16h 20m
1 stop
$278Multiple Airlines
Fri, Sep 11 - Sun, Sep 13
Breeze Airways Logo
10:56 am - 10:19 am
SWF
-
EYW
23h 23m
1 stop
Breeze Airways Logo
11:59 am - 11:39 am
EYW
-
SWF
23h 40m
1 stop
$280Breeze Airways
Sun, Sep 13 - Fri, Sep 18

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Allegiant Air flights from New Windsor to Key West

Our best Allegiant Air deals on New Windsor to Key West flight tickets
Allegiant Air
Nov 1
SWF7:19 pmNew Windsor Stewart
18h 35m
1 stop
EYW1:54 pmKey West
Nov 13
EYW8:25 amKey West
8h 15m
1 stop
SWF4:40 pmNew Windsor Stewart
$271
Allegiant Air
Oct 1
SWF7:36 pmNew Windsor Stewart
19h 50m
1 stop
EYW3:26 pmKey West
Oct 5
EYW9:24 amKey West
8h 59m
1 stop
SWF6:23 pmNew Windsor Stewart
$308
Allegiant Air
Sep 24
SWF11:13 amNew Windsor Stewart
5h 06m
1 stop
EYW4:19 pmKey West
Sep 27
EYW6:11 pmKey West
16h 20m
1 stop
SWF10:31 amNew Windsor Stewart
$323

Breeze Airways flights from New Windsor to Key West

Our best Breeze Airways deals on New Windsor to Key West flight tickets
Breeze Airways
Aug 30
SWF10:33 amNew Windsor Stewart
24h 54m
1 stop
EYW11:27 amKey West
Sep 25
EYW11:59 amKey West
23h 40m
1 stop
SWF11:39 amNew Windsor Stewart
$196
Breeze Airways
Aug 30
SWF10:33 amNew Windsor Stewart
24h 54m
1 stop
EYW11:27 amKey West
Sep 25
EYW12:59 pmKey West
22h 40m
2 stops
SWF11:39 amNew Windsor Stewart
$208
Breeze Airways
Aug 27
SWF10:33 amNew Windsor Stewart
24h 54m
1 stop
EYW11:27 amKey West
Aug 31
EYW12:07 pmKey West
23h 01m
1 stop
SWF11:08 amNew Windsor Stewart
$217

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor to Key West 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 July 25, 2026.
Use the filters below to find and compare flights from New Windsor to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/30

10:33 am-11:27 am

1 stop24h 54m

Key West

Fri 9/25

11:59 am-11:39 am

1 stop23h 40m

$196

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 8/30

10:33 am-11:27 am

1 stop24h 54m

Key West

Fri 9/25

12:59 pm-11:39 am

2 stops22h 40m

$208

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 8/27

10:33 am-11:27 am

1 stop24h 54m

Key West

Mon 8/31

12:07 pm-11:08 am

1 stop23h 01m

$217

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 8/29

12:05 pm-10:24 am

2 stops22h 19m

Key West

Mon 8/31

12:07 pm-11:08 am

1 stop23h 01m

$253

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 8/26

12:05 pm-11:25 am

2 stops23h 20m

Key West

Mon 8/31

12:07 pm-11:08 am

1 stop23h 01m

$259

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 8/29

12:05 pm-10:24 am

2 stops22h 19m

Key West

Sat 9/5

3:48 pm-10:23 am

1 stop18h 35m

$269

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 8/26

12:05 pm-11:25 am

2 stops23h 20m

Key West

Mon 8/31

12:07 pm-11:08 am

1 stop23h 01m

$270
Quickest round-trip

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Fri 9/11

12:16 pm-9:24 am

2 stops21h 08m

Key West

Sun 9/13

6:11 pm-10:31 am

1 stop16h 20m

$272

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Fri 9/11

12:16 pm-9:24 am

2 stops21h 08m

Key West

Sun 9/13

6:11 pm-10:31 am

1 stop16h 20m

$278

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 9/13

10:56 am-10:19 am

1 stop23h 23m

Key West

Fri 9/18

11:59 am-11:39 am

1 stop23h 40m

$280

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 Key West from

How to get the cheapest flight ticket from New Windsor to Key West

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 Key West?

On average, the least expensive day to fly to Key West from New Windsor is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $439. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Thursday, the most expensive travel day of the week, you can expect to see flight prices from New Windsor to Key West for around $581.

What is the cheapest time of day to depart on your flight to Key West?

According to our data, the cheapest time of day to fly to Key West is in the morning. momondo users have found flights departing from New Windsor to Key West in the morning for as low as $494. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Key West are more costly at noon, with an average ticket price of $517. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from New Windsor to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from New Windsor to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap New Windsor to Key West (SWF to EYW) flight deals and tips

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

Fastest flight time

14h 32m

Direct flights

None
The fastest flight from New Windsor to Key West takes 14h 32m
There are no direct flights from New Windsor to Key West. There are no popular flight routes from New Windsor to Key West.
Search flight deals

Frequently asked questions about flying from New Windsor to Key West

  • How far is New Windsor Stewart to Key West by plane?

    Key West is 1250.8 mi away from New Windsor Stewart. In terms of flight time, this usually takes a little over 14h 32m.

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

    Prices for flights from New Windsor Stewart Airport to Key West Airport are updated daily.

  • How old do you have to be to fly from New Windsor Stewart Airport to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New Windsor Stewart Airport to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents required for your trip to Key West Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Key West Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

Why should I use momondo to find a flight deal from New Windsor to Key West?

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

Can I find flights from New Windsor to Key West with flexible booking policies on momondo?

All flight searches from New Windsor to Key West on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from New Windsor to Key West?

Once you have performed a search for New Windsor to Key West 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 Key West right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Key West from New Windsor. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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