$146 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 5/19. 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.
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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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Flights Deals

Best Florida Keys Flight Deals from New Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Key West
Key West1 stop$233
Key West
Key West1 stop$233

Cheap Flight Deals from New Windsor to Florida Keys (SWF-zzEOA)

 
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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Windsor to Florida Keys.
Discover the best prices for you by selecting your travel dates on KAYAK.
Breeze Airways Logo
7:52 pm - 1:17 pmSWF-EYW
17h 25m1 stop
Breeze Airways Logo
10:12 am - 7:12 pmEYW-SWF
9h 00m1 stop
$233Breeze Airways
Find Deal
Sun, Jun 15 - Thu, Jun 19
Allegiant Air Logo
7:28 pm - 9:33 amSWF-EYW
14h 05m1 stop
Allegiant Air Logo
4:46 pm - 10:33 amEYW-SWF
17h 47m1 stop
$280Allegiant Air
Find Deal
Sun, May 18 - Wed, May 21
Allegiant Air Logo
6:42 pm - 9:52 amSWF-EYW
15h 10m1 stop
Allegiant Air Logo
2:45 pm - 10:21 amEYW-SWF
19h 36m1 stop
$307Allegiant Air
Find Deal
Wed, May 28 - Wed, Jun 4
Breeze Airways Logo
7:52 pm - 1:17 pmSWF-EYW
17h 25m1 stop
Breeze Airways Logo
10:12 am - 7:12 pmEYW-SWF
9h 00m1 stop
$312Breeze Airways
Find Deal
Sun, Jun 15 - Sun, Jun 22
Breeze Airways Logo
7:52 pm - 1:17 pmSWF-EYW
17h 25m1 stop
Breeze Airways Logo
10:12 am - 11:56 amEYW-SWF
25h 44m1 stop
$324Breeze Airways
Find Deal
Sun, Jun 15 - Mon, Jun 23
Allegiant Air Logo
11:01 am - 9:42 amSWF-EYW
22h 41m1 stop
Allegiant Air Logo
4:03 pm - 10:21 amEYW-SWF
18h 18m1 stop
$330Allegiant Air
Find Deal
Sat, Jun 14 - Sat, Jun 21
Breeze Airways Logo
7:52 pm - 1:17 pmSWF-EYW
17h 25m1 stop
Breeze Airways Logo
10:12 am - 7:12 pmEYW-SWF
9h 00m1 stop
$345Breeze Airways
Find Deal
Thu, Jun 19 - Sun, Jun 22
Breeze Airways Logo
7:52 pm - 1:17 pmSWF-EYW
17h 25m1 stop
Breeze Airways Logo
10:12 am - 7:12 pmEYW-SWF
9h 00m1 stop
$346Breeze Airways
Find Deal
Thu, Jun 19 - Sun, Jun 22
Allegiant Air Logo
7:28 pm - 3:22 pmSWF-EYW
19h 54m2 stops
Allegiant Air Logo
4:46 pm - 10:33 amEYW-SWF
17h 47m1 stop
$349Allegiant Air
Find Deal
Sun, May 18 - Wed, May 21
 Logo
11:13 am - 9:33 amSWF-EYW
22h 20m1 stop
 Logo
10:02 am - 7:06 pmEYW-SWF
33h 04m2 stops
Thu, Jul 24 - Sun, Jul 27
Useful Info

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.

Which airlines provide the cheapest flights from New Windsor to Florida Keys?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from New Windsor to Florida Keys were found on Breeze Airways ($233) and Allegiant Air ($280).


Good to know

Low seasonSeptember
High seasonMay
Cheapest flight$146
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 3% 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.

  • 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.

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 7961 reviews
6.6Boarding
5.1Food
5.9Comfort
5.0Entertainment
7.1Crew
Airline reviews

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

2.0 MediocreAnonymous, Apr 2025DTW - MCO
Read more Spirit Airlines reviews

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Perfect for the money paid. Flight from Indianapolis to Fort Lauderdale. Very courteous airport staff and crew. The boarding process went very smooth. Indianapolis was in the middle of several sever storms, delaying boarding and they found a window between the storms, asked everyone for a quick boarding and we departed before we would be held longer by the next storm front. A little rough air 20 min or so after take off, however I’ll take that to being grounded the whole night. Seats kind of small, kind of hard, but very doable for the 2.5 hrs flight. Snacks and drinks available for purchase. We didn’t, as it was a late night flight. One of the checked luggage came wet in Florida and clothes inside got wet from the water that infiltrated through the zipper, I’m assuming it was in the rain in Indianapolis, I cannot blame Spirit as I think the baggage handlers are hired by the airport. I’ll be more careful next time, as I have suitcases that are more water proof and maybe I should only purchase that kind.

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

The flight was on time. The seats are very narrow.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

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