$95 Find Cheap Flights from Stewart Intl. 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 8/26. 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
Miami1 stop$218
Key West
Key West1 stop$246
Miami
Miami1 stop$218
Key West
Key West1 stop$246

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

Wed, Aug 19 - Sat, Aug 22
Multiple Airlines Logo
12:05 pm - 10:16 am
SWF
-
MIA
22h 11m
1 stop
Multiple Airlines Logo
5:05 am - 11:25 am
MIA
-
SWF
6h 20m
1 stop
$218Multiple Airlines
Sun, May 31 - Thu, Jun 4
Multiple Airlines Logo
9:38 am - 11:27 am
SWF
-
EYW
25h 49m
1 stop
Multiple Airlines Logo
9:16 pm - 8:49 am
EYW
-
SWF
11h 33m
1 stop
$246Multiple Airlines
Sat, Sep 5 - Thu, Sep 10
Multiple Airlines Logo
12:05 pm - 7:13 pm
SWF
-
EYW
31h 08m
2 stops
Multiple Airlines Logo
6:11 pm - 10:16 am
EYW
-
SWF
16h 05m
1 stop
$254Multiple Airlines
Wed, Jul 8 - Wed, Jul 22
Multiple Airlines Logo
12:05 pm - 8:30 pm
SWF
-
MIA
8h 25m
1 stop
Multiple Airlines Logo
5:28 pm - 9:38 am
MIA
-
SWF
16h 10m
2 stops
$260Multiple Airlines
Thu, May 28 - Thu, Jun 4
Multiple Airlines Logo
9:38 am - 11:27 am
SWF
-
EYW
25h 49m
1 stop
Multiple Airlines Logo
9:16 pm - 8:49 am
EYW
-
SWF
11h 33m
1 stop
$262Multiple Airlines
Wed, Jul 8 - Tue, Jul 21
Multiple Airlines Logo
12:05 pm - 8:30 pm
SWF
-
MIA
8h 25m
1 stop
Multiple Airlines Logo
3:07 pm - 11:25 am
MIA
-
SWF
20h 18m
1 stop
$268Multiple Airlines
Sat, Jul 11 - Fri, Jul 24
Allegiant Air Logo
6:44 pm - 12:48 pm
SWF
-
EYW
18h 04m
1 stop
Allegiant Air Logo
3:27 pm - 5:54 pm
EYW
-
SWF
26h 27m
1 stop
$279Allegiant Air
Sun, Aug 9 - Fri, Aug 14
Breeze Airways Logo
9:38 am - 11:27 am
SWF
-
EYW
25h 49m
1 stop
Breeze Airways Logo
11:07 am - 11:25 am
EYW
-
SWF
24h 18m
1 stop
$286Breeze Airways
Thu, Jun 4 - Tue, Jun 9
Breeze Airways Logo
9:38 am - 11:27 am
SWF
-
EYW
25h 49m
1 stop
Breeze Airways Logo
1:14 pm - 11:25 am
EYW
-
SWF
22h 11m
2 stops
$288Breeze Airways
Tue, Oct 13 - Thu, Oct 22
Allegiant Air Logo
12:38 pm - 12:02 pm
SWF
-
EYW
23h 24m
1 stop
Allegiant Air Logo
8:36 pm - 4:49 pm
EYW
-
SWF
20h 13m
1 stop
$296Allegiant Air
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 $253, 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 October and June, when the average cost of round-trip tickets is $454 and $357 respectively.

Find deals

Good to know

Cheapest flight$95
Most popular time to fly and prices are also 77% lower on average.
Flight from Stewart Intl. to Miami

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 airline 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.
7.1
JetBlueOverall score based on 2979 reviews
7.3Boarding
7.2Entertainment
6.6Food
7.9Crew
7.5Comfort
Airline reviews

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

6.0 GoodAnonymous, May 2026
JFK - SFO
Read more JetBlue reviews

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

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.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

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.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

Stewart Intl. (SWF)