Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from New Windsor to Key West from $108

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 4/26. 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

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 Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$245Breeze Airways
Sun, Mar 22 - Wed, Mar 25
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$252Breeze Airways
Sun, Mar 22 - Wed, Mar 25
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$267Breeze Airways
Thu, Apr 9 - Wed, Apr 15
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$269Breeze Airways
Sun, Apr 12 - Thu, Apr 16
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$270Breeze Airways
Thu, Apr 9 - Wed, Apr 15
Multiple Airlines Logo
9:38 am - 11:30 am
SWF
-
EYW
25h 52m
1 stop
Multiple Airlines Logo
2:48 pm - 7:20 pm
EYW
-
SWF
28h 32m
1 stop
$273Multiple Airlines
Sun, May 24 - Sat, May 30
Multiple Airlines Logo
8:04 pm - 12:31 pm
SWF
-
EYW
16h 27m
1 stop
Multiple Airlines Logo
9:16 pm - 8:49 am
EYW
-
SWF
11h 33m
1 stop
$275Multiple Airlines
Sun, Jun 7 - Sun, Jun 14
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$276Breeze Airways
Thu, Apr 9 - Thu, Apr 16
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$277Breeze Airways
Thu, Apr 9 - Wed, Apr 15
Multiple Airlines Logo
12:05 pm - 10:24 am
SWF
-
EYW
22h 19m
2 stops
Multiple Airlines Logo
9:24 pm - 8:51 am
EYW
-
SWF
11h 27m
1 stop
$279Multiple Airlines
Wed, May 27 - Sun, May 31

Breeze Airways flights from New Windsor to Key West

Our best Breeze Airways deals on New Windsor to Key West flight tickets
Breeze Airways
Mar 22
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Mar 25
EYW11:51 amKey West
23h 17m
1 stop
SWF11:08 amNew Windsor Stewart
$245
Breeze Airways
Mar 22
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Mar 25
EYW11:51 amKey West
23h 17m
1 stop
SWF11:08 amNew Windsor Stewart
$252
Breeze Airways
Apr 9
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Apr 15
EYW11:51 amKey West
23h 17m
1 stop
SWF11:08 amNew Windsor Stewart
$267

Allegiant Air flights from New Windsor to Key West

Our best Allegiant Air deals on New Windsor to Key West flight tickets
Allegiant Air
Apr 23
SWF7:57 pmNew Windsor Stewart
18h 46m
1 stop
EYW2:43 pmKey West
Apr 26
EYW4:38 pmKey West
18h 12m
1 stop
SWF10:50 amNew Windsor Stewart
$373
Allegiant Air
Apr 23
SWF11:45 amNew Windsor Stewart
22h 26m
2 stops
EYW10:11 amKey West
Apr 26
EYW4:38 pmKey West
18h 12m
1 stop
SWF10:50 amNew Windsor Stewart
$381
Allegiant Air
May 17
SWF7:47 pmNew Windsor Stewart
18h 56m
1 stop
EYW2:43 pmKey West
May 23
EYW2:48 pmKey West
28h 32m
1 stop
SWF7:20 pmNew Windsor Stewart
$398

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 March 12, 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 3/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 3/25

11:51 am-11:08 am

1 stop23h 17m

$245

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 3/25

11:51 am-11:08 am

1 stop23h 17m

$252

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 4/9

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 4/15

11:51 am-11:08 am

1 stop23h 17m

$267

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 4/12

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 4/16

9:46 am-11:31 am

2 stops25h 45m

$269

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 4/9

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 4/15

11:51 am-11:08 am

1 stop23h 17m

$270

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 5/24

9:38 am-11:30 am

1 stop25h 52m

Key West

Sat 5/30

2:48 pm-7:20 pm

1 stop28h 32m

$273
Quickest round-trip

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 6/7

8:04 pm-12:31 pm

1 stop16h 27m

Key West

Sun 6/14

9:16 pm-8:49 am

1 stop11h 33m

$275

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 4/9

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 4/16

9:46 am-11:31 am

2 stops25h 45m

$276

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 4/9

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 4/15

11:51 am-11:08 am

1 stop23h 17m

$277

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Wed 5/27

12:05 pm-10:24 am

2 stops22h 19m

Key West

Sun 5/31

9:24 pm-8:51 am

1 stop11h 27m

$279

Flights are sorted by cheapest round-trip flights first.

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

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 $431. 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 $580.

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 $487. 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 $511. 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

5h 06m

Direct flights

None
The fastest flight from New Windsor to Key West takes 5h 06m
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

  • 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 5h 06m.

  • 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.

An easier way to manage your Key West 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
Sat 4/11
Sat 4/18
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States