$84 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 5/9. 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 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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Flight Deals

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$384
Key West
Key West1 stop$201
Miami
Miami1 stop$384
Key West
Key West1 stop$201

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, 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
$201Breeze Airways
Sun, Feb 22 - Thu, Feb 26
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$271Breeze Airways
Sun, Apr 26 - Wed, Apr 29
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, Feb 22 - Thu, Feb 26
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$289Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
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
Sun, Feb 22 - Sun, Mar 1
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:13 pm - 10:13 am
EYW
-
SWF
18h 00m
1 stop
$315Multiple Airlines
Thu, Mar 5 - Sun, Mar 8
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
4:14 pm - 10:12 am
EYW
-
SWF
17h 58m
1 stop
$339Multiple Airlines
Thu, Feb 26 - Sun, Mar 1
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, Mar 5 - Thu, Mar 12
Breeze Airways Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Breeze Airways Logo
9:46 am - 11:31 am
EYW
-
SWF
25h 45m
2 stops
$342Breeze Airways
Thu, Feb 26 - Sun, Mar 1
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
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 $248, prices are generally cheapest when you fly direct.

Good to know

Low seasonJuly
Cheapest flight$84
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 51% 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 airlines 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.
7.2
JetBlueOverall score based on 2893 reviews
7.2Entertainment
8.0Crew
6.6Food
7.5Comfort
7.4Boarding
Airline reviews

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

2.0 MediocreAnonymous, Jan 2026
JFK - BNA
Read more JetBlue reviews

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

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.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

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.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

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

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

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 love how they show love to their customers and care about them too.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports