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Florida Keys

$90+ Cheap flights from Islip, NY (ISP) to Florida Keys

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Islip to Florida Keys

Cheapest flights from Islip to Florida Keys
Explore the most affordable flight options available from Islip to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/276:40 pmISP - EYW
1 stop13h 35mMultiple Airlines
Tue 12/3012:20 pmEYW - ISP
2 stops28h 17mMultiple Airlines
Deal found 12/21$526
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Fri 12/262:25 pmISP - MIA
2 stops34h 22mMultiple Airlines
Thu 1/12:47 pmMIA - ISP
1 stop22h 58mMultiple Airlines
Deal found 12/20$622
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Fri 12/262:25 pmISP - MIA
2 stops14h 35mMultiple Airlines
Sun 12/283:08 pmMIA - ISP
1 stop22h 37mMultiple Airlines
Deal found 12/22$690
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Fri 12/268:35 pmISP - EYW
2 stops16h 55mMultiple Airlines
Mon 12/291:10 pmEYW - ISP
1 stop6h 30mMultiple Airlines
Deal found 12/21$690
This Southwest deal was found by Cheapflights users on 12/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:55 amISP - MIA
1 stop4h 45mSouthwest
Wed 1/77:15 amMIA - ISP
1 stop4h 40mSouthwest
Deal found 12/20$737
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/314:40 pmISP - EYW
1 stop18h 40mMultiple Airlines
Sat 1/37:47 amEYW - ISP
1 stop16h 12mMultiple Airlines
Deal found 12/22$758
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/246:00 amISP - MIA
2 stops18h 47mMultiple Airlines
Thu 1/12:47 pmMIA - ISP
1 stop22h 58mMultiple Airlines
Deal found 12/22$770
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:40 pmISP - MIA
1 stop5h 20mSouthwest
Sat 1/35:50 amMIA - ISP
1 stop5h 55mSouthwest
Deal found 12/21$842
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:15 amISP - MIA
1 stop5h 50mSouthwest
Wed 12/317:10 amMIA - ISP
1 stop5h 05mSouthwest
Deal found 12/21$887
This Southwest deal was found by Cheapflights users on 12/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2710:20 amISP - MIA
1 stop8h 40mSouthwest
Tue 12/3012:10 pmMIA - ISP
1 stop5h 05mSouthwest
Deal found 12/22$892
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:30 amISP - MIA
2 stops12h 30mSouthwest
Sun 12/286:15 amMIA - ISP
1 stop5h 40mSouthwest
Deal found 12/21$898
This Booking.com deal was found by Cheapflights users on 12/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:21 pmISP - EYW
2 stops40h 09mBreeze Airways
Sat 1/37:47 amEYW - ISP
2 stops27h 13mBreeze Airways
Deal found 12/22$942

Find flight deals from Islip to Florida Keys

Keep the following information in mind while searching for Islip to Florida Keys flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$180
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$310
Provider with most accurate pricing for New York (NYC)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Miami flights.
Search Deals
From Islip Long Island to Florida Keys
Search Deals
One-way flight from Islip Long Island to Florida Keys
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Florida Keys 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 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Islip to Florida Keys that are best for you.

Fly from

Islip

Fly to

Florida Keys

Route

Depart

Return

Price

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 2/21

5:07 pm-3:40 pm

2 stops22h 33m

Miami

Thu 2/26

11:28 am-1:31 pm

1 stop26h 03m

$202

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 1/21

11:50 am-3:41 pm

1 stop27h 51m

Miami

Tue 1/27

7:00 am-11:10 am

2 stops28h 10m

$203

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Mon 1/5

4:40 pm-11:20 am

1 stop18h 40m

Key West

Fri 1/9

9:49 am-11:10 am

2 stops25h 21m

$223

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Fri 2/13

2:31 pm-12:42 am

2 stops34h 11m

Miami

Sun 2/22

9:00 am-1:31 pm

1 stop28h 31m

$254

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Tue 1/27

3:45 pm-9:00 pm

1 stop5h 15m

Miami

Thu 1/29

7:15 am-11:55 am

1 stop4h 40m

$282

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 2/7

5:45 am-2:50 pm

1 stop9h 05m

Miami

Wed 2/11

4:30 pm-9:55 pm

1 stop5h 25m

$287

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Wed 1/7

11:50 am-10:21 am

2 stops22h 31m

Key West

Sun 1/11

10:06 am-7:45 pm

1 stop9h 39m

$292

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Mon 3/9

5:55 pm-11:00 pm

1 stop5h 05m

Miami

Tue 3/17

6:10 am-11:45 am

1 stop5h 35m

$317

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 1/21

3:45 pm-9:00 pm

1 stop5h 15m

Miami

Mon 1/26

7:15 am-11:55 am

1 stop4h 40m

$319

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Mon 1/19

11:50 am-5:10 pm

1 stop5h 20m

Miami

Thu 1/22

6:55 am-2:35 pm

1 stop7h 40m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 28 results
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Best time to book a flight from Islip to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Islip with our price prediction graph.
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.

Cheapflights Insights

Everything you need to know about your flight from Islip to Florida Keys

What is the cheapest month to book a flight from Islip, New York to Florida Keys?

Currently, May is the cheapest month in which you can book a flight from Islip, New York to Florida Keys (average of $151). Flying from Islip, New York to Florida Keys in August is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated December 23, 2025.
Read reviews from past customers who have flown Southwest, JetBlue, and Spirit Airlines from Islip to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,896 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,194 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,076 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Islip to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Islip to Florida Keys?

    Most people fly from Islip Long Island (ISP) if they book a flight from Islip to Florida Keys. Islip Long Island is conveniently located just 7.2 mi from Islip’s city center.

  • How long is the flight from Islip, New York to Florida Keys?

    For as low as $282, Southwest can have you in Florida Keys from Islip, New York in 5h 15m. Islip, New York and Florida Keys are separated by a distance of 1114 mi.

  • What are the cheapest airlines to fly from Islip, New York to Florida Keys one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $29. Users have also found prices from $73 and $101 on Delta and Southwest, respectively.

  • Can I find deals for flights from Islip to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Islip to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Florida Keys.

  • Can I find deals for business class flights from Islip to Florida Keys?

    Yes. Cheapflights offers flight deals from Islip to Florida Keys by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Islip, New York to Florida Keys?

    Currently, May is the cheapest month in which you can book a flight from Islip, New York to Florida Keys (average of $151). Flying from Islip, New York to Florida Keys in August is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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