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Cheap flights from New Windsor to Florida Keys from $98

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 2/2. 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 Florida Keys

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:37 am - 11:20 am
SWF
-
EYW
23h 43m1 stop
Multiple Airlines Logo
3:46 pm - 6:43 pm
EYW
-
SWF
26h 57m1 stop
$221Multiple Airlines
Mon, Jan 5 - Thu, Jan 8
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m1 stop
Multiple Airlines Logo
1:06 pm - 12:39 pm
EYW
-
SWF
23h 33m1 stop
$240Multiple Airlines
Sun, Feb 8 - Fri, Feb 13
Allegiant Air Logo
10:48 am - 9:37 pm
SWF
-
EYW
10h 49m1 stop
Allegiant Air Logo
3:46 pm - 6:43 pm
EYW
-
SWF
26h 57m1 stop
$257Allegiant Air
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
10:48 am - 9:37 pm
SWF
-
EYW
10h 49m1 stop
Multiple Airlines Logo
12:51 pm - 10:19 am
EYW
-
SWF
21h 28m1 stop
$265Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
12:13 pm - 12:26 pm
SWF
-
EYW
24h 13m1 stop
Multiple Airlines Logo
12:51 pm - 10:19 am
EYW
-
SWF
21h 28m1 stop
$272Multiple Airlines
Thu, Jan 8 - Sun, Jan 11
Multiple Airlines Logo
11:37 am - 11:20 am
SWF
-
EYW
23h 43m1 stop
Multiple Airlines Logo
10:06 am - 11:31 am
EYW
-
SWF
25h 25m2 stops
$275Multiple Airlines
Mon, Jan 5 - Thu, Jan 8
Multiple Airlines Logo
10:48 am - 9:37 pm
SWF
-
EYW
10h 49m1 stop
Multiple Airlines Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m2 stops
$276Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
11:48 am - 1:30 pm
SWF
-
EYW
25h 42m2 stops
Multiple Airlines Logo
1:06 pm - 12:39 pm
EYW
-
SWF
23h 33m1 stop
$285Multiple Airlines
Sun, Feb 8 - Fri, Feb 13
Allegiant Air Logo
10:48 am - 9:37 pm
SWF
-
EYW
10h 49m1 stop
Allegiant Air Logo
4:21 pm - 10:14 am
EYW
-
SWF
17h 53m1 stop
$290Allegiant Air
Sun, Feb 8 - Thu, Feb 12
Multiple Airlines Logo
10:48 am - 9:37 pm
SWF
-
EYW
10h 49m1 stop
Multiple Airlines Logo
10:49 am - 9:58 am
EYW
-
SWF
23h 09m1 stop
$299Multiple Airlines
Thu, Jan 29 - Sat, Jan 31

Allegiant Air flights from New Windsor to Florida Keys

Our best Allegiant Air deals on New Windsor to Florida Keys flight tickets
Allegiant Air
Jan 29
SWF10:48 amNew Windsor Stewart
10h 49m
1 stop
EYW9:37 pmKey West
Feb 5
EYW3:46 pmKey West
26h 57m
1 stop
SWF6:43 pmNew Windsor Stewart
$257
Find similar
Allegiant Air
Feb 8
SWF10:48 amNew Windsor Stewart
10h 49m
1 stop
EYW9:37 pmKey West
Feb 12
EYW4:21 pmKey West
17h 53m
1 stop
SWF10:14 amNew Windsor Stewart
$290
Find similar
Allegiant Air
Feb 5
SWF10:48 amNew Windsor Stewart
10h 49m
1 stop
EYW9:37 pmKey West
Feb 8
EYW3:46 pmKey West
26h 57m
1 stop
SWF6:43 pmNew Windsor Stewart
$308
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
Jan 8
SWF12:13 pmNew Windsor Stewart
24h 13m
1 stop
EYW12:26 pmKey West
Jan 11
EYW10:06 amKey West
25h 25m
2 stops
SWF11:31 amNew Windsor Stewart
$335
Find similar
Breeze Airways
Dec 19
SWF12:24 pmNew Windsor Stewart
18h 43m
2 stops
EYW7:07 amKey West
Dec 22
EYW1:10 pmKey West
21h 53m
1 stop
SWF11:03 amNew Windsor Stewart
$416
Find similar
Breeze Airways
Dec 19
SWF12:24 pmNew Windsor Stewart
18h 43m
2 stops
EYW7:07 amKey West
Dec 22
EYW1:10 pmKey West
21h 53m
1 stop
SWF11:03 amNew Windsor Stewart
$442
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 December 17, 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 WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Mon 1/5

11:37 am-11:20 am

1 stop23h 43m

Key West

Thu 1/8

3:46 pm-6:43 pm

1 stop26h 57m

$221

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/8

11:48 am-12:26 pm

1 stop24h 38m

Key West

Fri 2/13

1:06 pm-12:39 pm

1 stop23h 33m

$240

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Thu 2/5

3:46 pm-6:43 pm

1 stop26h 57m

$257

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sun 2/1

12:51 pm-10:19 am

1 stop21h 28m

$265

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/8

12:13 pm-12:26 pm

1 stop24h 13m

Key West

Sun 1/11

12:51 pm-10:19 am

1 stop21h 28m

$272

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Mon 1/5

11:37 am-11:20 am

1 stop23h 43m

Key West

Thu 1/8

10:06 am-11:31 am

2 stops25h 25m

$275

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Thu 2/5

9:46 am-11:31 am

2 stops25h 45m

$276

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/8

11:48 am-1:30 pm

2 stops25h 42m

Key West

Fri 2/13

1:06 pm-12:39 pm

1 stop23h 33m

$285

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 2/8

10:48 am-9:37 pm

1 stop10h 49m

Key West

Thu 2/12

4:21 pm-10:14 am

1 stop17h 53m

$290

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 1/29

10:48 am-9:37 pm

1 stop10h 49m

Key West

Sat 1/31

10:49 am-9:58 am

1 stop23h 09m

$299

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 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

Fastest flight time

9h 27m

Direct flights

None
The fastest flight from New Windsor to Florida Keys takes 9h 27m
There are no direct flights from New Windsor to Florida Keys. There are no popular flight routes from New Windsor to Florida Keys.
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 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.
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