$108 Find Cheap Flights from New Windsor to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Florida Keys departing on 8/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Florida Keys, as well as popular online travel agencies
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Cheap Flights from New Windsor to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami2 stops$246
Key West
Key West1 stop$212
Miami
Miami2 stops$246
Key West
Key West1 stop$212

Book Cheap New Windsor to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Florida Keys that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Florida Keys

Sat, Aug 16 - Thu, Aug 21
Breeze Airways Logo
7:29 pm - 1:07 pmSWF-EYW
17h 38m1 stop
Breeze Airways Logo
10:02 am - 7:12 pmEYW-SWF
9h 10m1 stop
$212Breeze Airways
Find Deal
Sun, Aug 17 - Thu, Aug 21
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 7:12 pmEYW-SWF
9h 10m1 stop
$219Breeze Airways
Find Deal
Thu, Sep 11 - Sun, Sep 14
Breeze Airways Logo
11:33 am - 11:52 amSWF-EYW
24h 19m1 stop
Breeze Airways Logo
8:55 am - 11:44 amEYW-SWF
26h 49m2 stops
$224Breeze Airways
Find Deal
Fri, Oct 24 - Sun, Oct 26
 Logo
11:31 am - 12:13 pmSWF-MIA
24h 42m2 stops
 Logo
7:01 pm - 2:11 pmMIA-SWF
19h 10m2 stops
Fri, Oct 3 - Sun, Oct 5
 Logo
12:11 pm - 12:21 pmSWF-MIA
24h 10m2 stops
 Logo
5:59 pm - 10:11 amMIA-SWF
16h 12m2 stops
Fri, Oct 24 - Fri, Oct 31
 Logo
11:31 am - 12:13 pmSWF-MIA
24h 42m2 stops
 Logo
6:00 am - 7:16 pmMIA-SWF
13h 16m2 stops
Sun, Aug 10 - Sun, Aug 17
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 12:48 pmEYW-SWF
26h 46m2 stops
$295Breeze Airways
Find Deal
Thu, Nov 6 - Sun, Nov 9
Breeze Airways Logo
11:33 am - 11:52 amSWF-EYW
24h 19m1 stop
Breeze Airways Logo
8:55 am - 11:44 amEYW-SWF
26h 49m2 stops
$296Breeze Airways
Find Deal
Thu, Nov 13 - Mon, Nov 17
Allegiant Air Logo
6:14 pm - 8:11 amSWF-EYW
13h 57m1 stop
Allegiant Air Logo
10:41 am - 10:26 amEYW-SWF
23h 45m2 stops
$372Allegiant Air
Find Deal
Thu, Aug 14 - Sun, Aug 17
Allegiant Air Logo
8:33 pm - 9:33 amSWF-EYW
13h 00m1 stop
Allegiant Air Logo
8:53 am - 7:43 pmEYW-SWF
10h 50m1 stop
$517Allegiant Air
Find Deal
Booking Insights

KAYAK's insights & trends for New Windsor to Florida Keys flights

Get data-powered insights and trends into flights from New Windsor to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from New Windsor to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $224, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
Cheapest flight$108
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Stewart Intl. to Key West

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Stewart Intl. to Florida Keys?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stewart Intl. to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stewart Intl. to Florida Keys is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stewart Intl. to Florida Keys?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Stewart Intl. to Florida Keys with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. to Florida Keys?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Stewart Intl. to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida Keys?

    The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $131 on average. Morning departures are around 18% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the evening, which is peak travel time and where the average cost of a ticket is $161.

Reviews of the top airline flying from New Windsor to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from New Windsor to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from New Windsor to Florida Keys? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.3
Spirit AirlinesOverall score based on 8048 reviews
5.9Comfort
6.6Boarding
7.0Crew
5.0Entertainment
5.1Food
Airline reviews

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

2.0 MediocreNathaniel, Jul 2025ROC - FLL
Read more Spirit Airlines reviews

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

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