Latest deals
Insights
FAQs
Price Alerts

Cheap flights from New Windsor to Florida Keys from $114

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 2/21. 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

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
$201Breeze Airways
Sun, Mar 8 - Wed, Mar 11
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
$284Breeze Airways
Sun, Apr 26 - Wed, Apr 29
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:31 pm - 9:02 am
EYW
-
SWF
16h 31m
1 stop
$290Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Multiple Airlines Logo
11:52 am - 1:30 pm
SWF
-
EYW
25h 38m
1 stop
Multiple Airlines Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$341Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Allegiant Air Logo
7:28 pm - 2:47 pm
SWF
-
EYW
19h 19m
1 stop
Allegiant Air Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$342Allegiant Air
Thu, Feb 19 - Thu, Feb 26
Allegiant Air Logo
7:28 pm - 2:47 pm
SWF
-
EYW
19h 19m
1 stop
Allegiant Air Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$343Allegiant Air
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
11:52 am - 1:30 pm
SWF
-
EYW
25h 38m
1 stop
Multiple Airlines Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$344Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
11:45 am - 9:06 am
SWF
-
EYW
21h 21m
1 stop
Multiple Airlines Logo
11:51 am - 11:08 am
EYW
-
SWF
23h 17m
1 stop
$349Multiple Airlines
Sat, Apr 4 - Wed, Apr 8
Multiple Airlines Logo
7:28 pm - 9:09 am
SWF
-
EYW
13h 41m
1 stop
Multiple Airlines Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$357Multiple Airlines
Thu, Feb 19 - Thu, Feb 26
Multiple Airlines Logo
7:28 pm - 9:09 am
SWF
-
EYW
13h 41m
1 stop
Multiple Airlines Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$359Multiple Airlines
Thu, Feb 19 - Thu, Feb 26

Breeze Airways flights from New Windsor to Florida Keys

Our best Breeze Airways deals on New Windsor to Florida Keys flight tickets
Breeze Airways
Mar 8
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Mar 11
EYW11:51 amKey West
23h 17m
1 stop
SWF11:08 amNew Windsor Stewart
$201
Breeze Airways
Apr 26
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Apr 29
EYW11:51 amKey West
23h 17m
1 stop
SWF11:08 amNew Windsor Stewart
$284
Breeze Airways
Feb 19
SWF11:48 amNew Windsor Stewart
24h 38m
1 stop
EYW12:26 pmKey West
Feb 22
EYW9:46 amKey West
25h 45m
2 stops
SWF11:31 amNew Windsor Stewart
$491

Allegiant Air flights from New Windsor to Florida Keys

Our best Allegiant Air deals on New Windsor to Florida Keys flight tickets
Allegiant Air
Feb 19
SWF7:28 pmNew Windsor Stewart
19h 19m
1 stop
EYW2:47 pmKey West
Feb 26
EYW4:13 pmKey West
18h 00m
1 stop
SWF10:13 amNew Windsor Stewart
$342
Allegiant Air
Feb 19
SWF7:28 pmNew Windsor Stewart
19h 19m
1 stop
EYW2:47 pmKey West
Feb 26
EYW4:13 pmKey West
18h 00m
1 stop
SWF10:13 amNew Windsor Stewart
$343
Allegiant Air
Mar 12
SWF8:40 pmNew Windsor Stewart
17h 29m
1 stop
EYW2:09 pmKey West
Mar 15
EYW4:31 pmKey West
16h 31m
1 stop
SWF9:02 amNew Windsor Stewart
$392

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 February 6, 2026.
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

Sun 3/8

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 3/11

11:51 am-11:08 am

1 stop23h 17m

$201

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sun 4/26

11:48 am-12:26 pm

1 stop24h 38m

Key West

Wed 4/29

11:51 am-11:08 am

1 stop23h 17m

$284

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 3/5

11:48 am-12:26 pm

1 stop24h 38m

Key West

Thu 3/12

4:31 pm-9:02 am

1 stop16h 31m

$290

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/26

11:52 am-1:30 pm

1 stop25h 38m

Key West

Sun 3/1

4:13 pm-10:13 am

1 stop18h 00m

$341

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/19

7:28 pm-2:47 pm

1 stop19h 19m

Key West

Thu 2/26

4:13 pm-10:13 am

1 stop18h 00m

$342

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/19

7:28 pm-2:47 pm

1 stop19h 19m

Key West

Thu 2/26

4:13 pm-10:13 am

1 stop18h 00m

$343

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/26

11:52 am-1:30 pm

1 stop25h 38m

Key West

Sun 3/1

4:13 pm-10:13 am

1 stop18h 00m

$344

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Sat 4/4

11:45 am-9:06 am

1 stop21h 21m

Key West

Wed 4/8

11:51 am-11:08 am

1 stop23h 17m

$349

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/19

7:28 pm-9:09 am

1 stop13h 41m

Key West

Thu 2/26

9:46 am-11:31 am

2 stops25h 45m

$357

New WindsorKey West

SWF - EYW

SWFEYW

New Windsor Stewart

Thu 2/19

7:28 pm-9:09 am

1 stop13h 41m

Key West

Thu 2/26

9:46 am-11:31 am

2 stops25h 45m

$359

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

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

12h 44m

Direct flights

None
The fastest flight from New Windsor to Florida Keys takes 12h 44m
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 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
Sun 3/8
Sun 3/15
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 $49
Flights to Los Angelesfrom $46
Flights to Miamifrom $27
Flights to Chicagofrom $50
Flights to Orlandofrom $50
Flights to San Franciscofrom $54
Flights to Las Vegasfrom $44
Flights to Washington, D.C.from $51
Flights to Bostonfrom $50
Flights to Atlantafrom $46
Flights to Dallasfrom $49
Flights to Seattlefrom $65