$248+ Cheap flights from Islip, NY to Key West (ISP - EYW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Oct 16 — Oct 231
Round-trip
1 adult, Economy
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Find cheap flights from Islip to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Islip to Key West
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Best
Last-minute
One-way
Cheapest flights from Islip to Key WestExplore the most affordable flight options available from Islip to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Islip to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:43 pm -
1 stop16h 36m
Wed 9/3010:04 am -
2 stops24h 13m
Deal found 9/11![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:25 pm -
1 stop15h 54m
Sun 10/1810:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
2 stops22h 19m
Sun 10/1810:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:28 pm -
2 stops18h 51m
Thu 10/110:59 am -
1 stop5h 59m
Deal found 9/12![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:00 pm -
2 stops21h 24m
Mon 10/1911:59 am -
1 stop23h 21m
Deal found 9/13![Breeze Airways logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:00 pm -
2 stops23h 21m
Fri 9/1810:59 am -
1 stop5h 59m
Deal found 9/12![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:02 pm -
2 stops21h 34m
Mon 10/2610:59 am -
1 stop7h 01m
Deal found 9/12![Multiple Airlines logo]()
$520
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:33 pm -
1 stop15h 46m
Mon 11/3010:59 am -
2 stops25h 59m
Deal found 9/15![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:25 pm -
1 stop15h 54m
Sun 10/1110:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$628
Best flights from Islip to Key WestDiscover carefully curated flight deals from Islip to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Islip to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:43 pm -
1 stop16h 36m
Wed 9/3010:04 am -
2 stops24h 13m
Deal found 9/11![Multiple Airlines logo]()
$354
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2811:58 am -
2 stops24h 21m
Wed 2/312:19 pm -
2 stops22h 59m
Deal found 9/14![Breeze Airways logo]()
$654
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:28 pm -
2 stops18h 51m
Thu 10/110:59 am -
1 stop5h 59m
Deal found 9/12![Multiple Airlines logo]()
$402
This Trip.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/169:40 am -
1 stop25h 46m
Tue 1/1910:59 am -
2 stops47h 18m
Deal found 9/13![Breeze Airways logo]()
$683
This Trip.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/95:38 pm -
2 stops17h 01m
Sun 2/1410:59 am -
2 stops8h 27m
Deal found 9/15![Breeze Airways logo]()
$732
This Mytrip deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:00 pm -
2 stops22h 19m
Wed 9/3010:04 am -
2 stops32h 47m
Deal found 9/11![Breeze Airways logo]()
$738
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:28 pm -
2 stops18h 51m
Thu 10/110:59 am -
2 stops8h 06m
Deal found 9/12![Breeze Airways logo]()
$744
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2810:57 am -
1 stop24h 22m
Mon 2/110:59 am -
2 stops48h 04m
Deal found 9/14![Breeze Airways logo]()
$768
This Gotogate deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:57 am -
2 stops23h 22m
Sun 2/710:59 am -
2 stops27h 23m
Deal found 9/14![Breeze Airways logo]()
$798
This KAYAK deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:00 pm -
1 stop24h 42m
Sat 11/2110:04 am -
2 stops24h 13m
Deal found 9/11![Breeze Airways logo]()
$798
Last-minute flights from Islip to Key WestDiscover last-minute flight deals from Islip to Key West. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Islip to Key West. Data last updated September 16, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:00 pm -
2 stops23h 21m
Fri 9/1810:59 am -
1 stop5h 59m
Deal found 9/12![Multiple Airlines logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:43 pm -
1 stop16h 36m
Wed 9/3010:04 am -
2 stops24h 13m
Deal found 9/11![Multiple Airlines logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:28 pm -
2 stops18h 51m
Thu 10/110:59 am -
1 stop5h 59m
Deal found 9/12![Multiple Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:25 pm -
1 stop15h 54m
Sun 10/1110:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$628
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:25 pm -
1 stop15h 54m
Sun 10/1810:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1312:00 pm -
2 stops21h 24m
Mon 10/1911:59 am -
1 stop23h 21m
Deal found 9/13![Breeze Airways logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:00 pm -
2 stops22h 19m
Sun 10/1810:59 am -
1 stop6h 31m
Deal found 9/13![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:02 pm -
2 stops21h 34m
Mon 10/2610:59 am -
1 stop7h 01m
Deal found 9/12![Multiple Airlines logo]()
$520
One-way flights from Islip to Key WestSearch for one-way flight options from Islip to Key West. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Islip to Key West. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:43 pm -
1 stop16h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:26 pm -
2 stops18h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Breeze Airways logo]()
$275
This KAYAK deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/95:38 pm -
2 stops17h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Breeze Airways logo]()
$305
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/109:40 am -
1 stop25h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$375
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:45 pm -
2 stops14h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$410
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:02 pm -
2 stops21h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$490
This KAYAK deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1011:43 am -
2 stops22h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Breeze Airways logo]()
$530
Find flight deals from Islip to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $354 (Kiwi.com) |
One-way from | $248 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $437 |
Cheapflights Fare Finder
Customize your flight search to find flights from Islip to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 16, 2026.
Use the filters below to find and compare flights from Islip to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Thu 9/24
5:43 pm-10:19 am
1 stop16h 36m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$248
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Sat 9/26
5:43 pm-10:19 am
1 stop16h 36m
Key West
Wed 9/30
10:04 am-10:17 am
2 stops24h 13m
$354
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Sun 9/27
5:28 pm-12:19 pm
2 stops18h 51m
Key West
Thu 10/1
10:59 am-4:58 pm
1 stop5h 59m
$402
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Sun 11/1
10:57 am-11:19 am
1 stop24h 22m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$410
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Wed 3/10
11:43 am-10:19 am
2 stops22h 36m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$490
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Mon 10/12
3:02 pm-12:36 pm
2 stops21h 34m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$515
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Wed 2/10
11:43 am-10:19 am
2 stops22h 36m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$530
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Thu 1/28
11:58 am-12:19 pm
2 stops24h 21m
Key West
Wed 2/3
12:19 pm-11:18 am
2 stops22h 59m
$654
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Sat 1/16
9:40 am-11:26 am
1 stop25h 46m
Key West
Tue 1/19
10:59 am-10:17 am
2 stops47h 18m
$683
IslipKey West
ISP Islip Long Island - EYW Key West
ISPEYW
Islip Long Island
Tue 2/9
5:38 pm-10:39 am
2 stops17h 01m
Key West
Sun 2/14
10:59 am-7:26 pm
2 stops8h 27m
$732
Showing 1-10 of 16 resultsSorted by cheapest first
Compare providers for flights from Islip to Key West
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Key West in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Islip, New York-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Islip, New York-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Islip, New York-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Islip to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Islip with our price prediction graph.
ISP-EYW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Related info for your journey
Find useful and relevant information for your journey from Islip to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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