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Cheap flights from New Windsor to Key West from $95

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 3/1. 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

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Find the cheapest flights from New Windsor to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:14 pm - 10:12 am
EYW
-
SWF
17h 58m
1 stop
$228Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
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
$238Breeze Airways
Sun, Feb 22 - Thu, Feb 26
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
$241Breeze Airways
Sun, Feb 22 - Thu, Feb 26
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$243Multiple Airlines
Sun, Feb 22 - Thu, Feb 26
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
$249Breeze Airways
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:36 pm - 8:57 am
EYW
-
SWF
16h 21m
1 stop
$266Multiple Airlines
Sun, Mar 22 - Thu, Mar 26
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:14 pm - 10:12 am
EYW
-
SWF
17h 58m
1 stop
$269Multiple Airlines
Thu, Feb 26 - Thu, Mar 5
Multiple Airlines Logo
8:12 pm - 2:03 pm
SWF
-
EYW
17h 51m
1 stop
Multiple Airlines Logo
12:25 pm - 10:55 am
EYW
-
SWF
22h 30m
1 stop
$283Multiple Airlines
Sun, Apr 5 - Wed, Apr 8
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
$293Breeze Airways
Sun, Mar 22 - Thu, Mar 26
Allegiant Air Logo
7:22 pm - 2:45 pm
SWF
-
EYW
19h 23m
1 stop
Allegiant Air Logo
4:14 pm - 10:12 am
EYW
-
SWF
17h 58m
1 stop
$309Allegiant Air
Thu, Feb 26 - Thu, Mar 5

Breeze Airways flights from New Windsor to Key West

Our best Breeze Airways deals on New Windsor to Key West flight tickets
Breeze Airways
Feb 22
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Feb 26
EYW9:46 amKey West
25h 45m
2 stops
SWF11:31 amNew Windsor Stewart
$238
Breeze Airways
Feb 22
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Feb 26
EYW9:46 amKey West
25h 45m
2 stops
SWF11:31 amNew Windsor Stewart
$241
Breeze Airways
Mar 1
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Mar 5
EYW9:46 amKey West
25h 45m
2 stops
SWF11:31 amNew Windsor Stewart
$249

Allegiant Air flights from New Windsor to Key West

Our best Allegiant Air deals on New Windsor to Key West flight tickets
Allegiant Air
Feb 26
SWF7:22 pmNew Windsor Stewart
19h 23m
1 stop
EYW2:45 pmKey West
Mar 5
EYW4:14 pmKey West
17h 58m
1 stop
SWF10:12 amNew Windsor Stewart
$309
Allegiant Air
Mar 15
SWF8:40 pmNew Windsor Stewart
17h 29m
1 stop
EYW2:09 pmKey West
Mar 22
EYW4:41 pmKey West
16h 16m
1 stop
SWF8:57 amNew Windsor Stewart
$388
Allegiant Air
Mar 5
SWF7:27 pmNew Windsor Stewart
19h 26m
1 stop
EYW2:53 pmKey West
Mar 8
EYW4:14 pmKey West
17h 58m
1 stop
SWF10:12 amNew Windsor Stewart
$403

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 February 10, 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

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/1

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/5

4:14 pm-10:12 am

1 stop17h 58m

$228

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 2/26

9:46 am-11:31 am

2 stops25h 45m

$238

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 2/26

9:46 am-11:31 am

2 stops25h 45m

$241

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 2/26

4:13 pm-10:13 am

1 stop18h 00m

$243

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/1

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/5

9:46 am-11:31 am

2 stops25h 45m

$249

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/26

4:36 pm-8:57 am

1 stop16h 21m

$266

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/26

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/5

4:14 pm-10:12 am

1 stop17h 58m

$269

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 4/5

8:12 pm-2:03 pm

1 stop17h 51m

Key West

Wed 4/8

12:25 pm-10:55 am

1 stop22h 30m

$283

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 3/22

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/26

9:46 am-11:31 am

2 stops25h 45m

$293

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/26

7:22 pm-2:45 pm

1 stop19h 23m

Key West

Thu 3/5

4:14 pm-10:12 am

1 stop17h 58m

$309

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 $436. 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 $579.

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 $490. 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 $498. 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 52m

Direct flights

None
The fastest flight from New Windsor to Key West takes 14h 52m
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 14h 52m.

  • 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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