$136 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 6/29. 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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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
Miami
Miami2 stops$293
Key West
Key West1 stop$226
Miami
Miami2 stops$293
Key West
Key West1 stop$226

Cheap Flights from New Windsor to Florida Keys

 
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

Thu, Sep 4 - Sun, Sep 7
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
$226Breeze Airways
Find Deal
Thu, Sep 11 - Sun, Sep 21
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
$266Breeze Airways
Find Deal
Sun, Jul 27 - Mon, Aug 4
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 11:56 amEYW-SWF
25h 54m1 stop
$282Breeze Airways
Find Deal
Wed, Jul 30 - Wed, Aug 6
Allegiant Air Logo
7:00 pm - 4:45 pmSWF-EYW
21h 45m1 stop
Allegiant Air Logo
4:00 pm - 7:13 pmEYW-SWF
27h 13m1 stop
$292Allegiant Air
Find Deal
Fri, Aug 15 - Sun, Aug 24
 Logo
7:37 pm - 2:20 pmSWF-MIA
18h 43m2 stops
 Logo
7:05 pm - 4:46 pmMIA-SWF
21h 41m2 stops
Fri, Aug 1 - Thu, Aug 14
 Logo
7:56 pm - 8:04 pmSWF-MIA
24h 08m2 stops
 Logo
7:05 pm - 6:47 pmMIA-SWF
23h 42m2 stops
Thu, Jul 31 - Mon, Aug 4
Breeze Airways Logo
7:52 pm - 1:07 pmSWF-EYW
17h 15m1 stop
Breeze Airways Logo
10:02 am - 11:56 amEYW-SWF
25h 54m1 stop
$300Breeze Airways
Find Deal
Wed, Jul 16 - Wed, Jul 23
Allegiant Air Logo
7:00 pm - 4:45 pmSWF-EYW
21h 45m1 stop
Allegiant Air Logo
3:55 pm - 10:23 amEYW-SWF
18h 28m1 stop
$303Allegiant Air
Find Deal
Mon, Aug 18 - Thu, Aug 21
 Logo
7:37 pm - 6:52 pmSWF-MIA
23h 15m2 stops
 Logo
7:05 pm - 4:46 pmMIA-SWF
21h 41m2 stops
Sun, Aug 3 - Wed, Aug 6
Allegiant Air Logo
11:13 am - 9:33 amSWF-EYW
22h 20m1 stop
Allegiant Air Logo
4:00 pm - 7:13 pmEYW-SWF
27h 13m1 stop
$340Allegiant Air
Find Deal
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.

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 $221, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
High seasonMay
Cheapest flight$136
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 19% 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 8064 reviews
5.0Entertainment
5.1Food
5.9Comfort
7.1Crew
6.6Boarding
Airline reviews

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

10.0 ExcellentAnonymous, Jun 2025CLT - FLL
Read more Spirit Airlines reviews

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.

My experience with spirit was terrible. Customer service was terrible. Flight got canceled abruptly with no accommodations made for the inconvenience or any sort of help. I was unable to rebook a new flight.

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.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

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