$96 Find Cheap Flights from Stewart Intl. to Florida Keys - Compare and Save

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 8/30. 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, 0 bags

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 Stewart Intl. 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 Stewart Intl. 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$372
Key West
Key West1 stop$230
Miami
Miami2 stops$372
Key West
Key West1 stop$230

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

Sun, Sep 13 - Thu, Sep 17
Multiple Airlines Logo
10:56 am - 10:19 am
SWF
-
EYW
23h 23m
1 stop
Multiple Airlines Logo
6:11 pm - 10:16 am
EYW
-
SWF
16h 05m
1 stop
$230Multiple Airlines
Sun, Sep 6 - Thu, Sep 10
Multiple Airlines Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Multiple Airlines Logo
6:11 pm - 10:16 am
EYW
-
SWF
16h 05m
1 stop
$247Multiple Airlines
Sun, Aug 30 - Sat, Sep 5
Multiple Airlines Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Multiple Airlines Logo
3:48 pm - 10:23 am
EYW
-
SWF
18h 35m
1 stop
$251Multiple Airlines
Wed, Aug 5 - Tue, Aug 11
Multiple Airlines Logo
7:58 pm - 1:31 pm
SWF
-
EYW
17h 33m
1 stop
Multiple Airlines Logo
1:14 pm - 11:25 am
EYW
-
SWF
22h 11m
2 stops
$255Multiple Airlines
Sat, Aug 8 - Tue, Aug 11
Multiple Airlines Logo
4:40 pm - 1:31 pm
SWF
-
EYW
20h 51m
1 stop
Multiple Airlines Logo
1:14 pm - 11:25 am
EYW
-
SWF
22h 11m
2 stops
$257Multiple Airlines
Thu, Sep 24 - Sun, Sep 27
Allegiant Air Logo
11:13 am - 8:08 am
SWF
-
EYW
20h 55m
1 stop
Allegiant Air Logo
6:11 pm - 10:31 am
EYW
-
SWF
16h 20m
1 stop
$263Allegiant Air
Sat, Aug 8 - Thu, Aug 13
Multiple Airlines Logo
4:40 pm - 1:31 pm
SWF
-
EYW
20h 51m
1 stop
Multiple Airlines Logo
12:05 pm - 11:37 am
EYW
-
SWF
23h 32m
2 stops
$265Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
10:56 am - 10:19 am
SWF
-
EYW
23h 23m
1 stop
Multiple Airlines Logo
6:11 pm - 10:31 am
EYW
-
SWF
16h 20m
1 stop
$267Multiple Airlines
Sat, Aug 8 - Wed, Aug 12
Multiple Airlines Logo
4:40 pm - 1:31 pm
SWF
-
EYW
20h 51m
1 stop
Multiple Airlines Logo
11:46 am - 9:38 am
EYW
-
SWF
21h 52m
2 stops
$272Multiple Airlines
Thu, Aug 6 - Thu, Aug 13
Breeze Airways Logo
10:33 am - 11:27 am
SWF
-
EYW
24h 54m
1 stop
Breeze Airways Logo
12:05 pm - 11:37 am
EYW
-
SWF
23h 32m
2 stops
$274Breeze Airways
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 Stewart Intl. 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 $254, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Stewart Intl. to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New Windsor to Florida Keys, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Stewart Intl. to Florida Keys is November, when tickets cost $0 (return) on average. On the other hand, the most expensive months are June and October, when the average cost of round-trip tickets is $357 and $227 respectively.

Good to know

Cheapest flight$96
Most popular time to fly and prices are also 82% lower on average.
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.

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

 
See real verified KAYAK customer reviews for airlines flying from Stewart Intl. 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.
7.3
Allegiant AirOverall score based on 689 reviews
7.6Boarding
5.4Entertainment
8.1Crew
5.8Food
6.9Comfort
Airline reviews

Allegiant canceled the flight. The flight the next day was full. Allegiant did not provide any compensation besides a refund. Last time on Allegiant.

2.0 MediocreSpencer, Jun 2026
SDF - PGD
Read more Allegiant Air reviews

Allegiant canceled the flight. The flight the next day was full. Allegiant did not provide any compensation besides a refund. Last time on Allegiant.

Great. No choice for n/a. No food or entertainment options

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

Web site and app most difficult to access. Tel number not accessible. No answer at any time of day.

Plane had mechanic problem that was never explained. Had to bring a plane from another airport. Six hour delay. No apology for the delay. Not even an acknowledgment.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

Communication since no reason or explanation was given for 3 hrs delay

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports