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Florida Keys

$136+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — EYW
Jun 22 — Jun 291
Mon 6/22
Mon 6/29
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 May 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/18. 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 8/1911:57 am
ISP
-
MIA
1 stop22h 19m
Multiple Airlines
Sat 8/225:05 am
MIA
-
ISP
1 stop6h 12m
Multiple Airlines
Deal found 5/18$232
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/129:52 pm
ISP
-
EYW
2 stops36h 14m
Multiple Airlines
Fri 6/1912:07 pm
EYW
-
ISP
1 stop8h 50m
Multiple Airlines
Deal found 5/18$287
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Wed 6/1011:57 am
ISP
-
MIA
1 stop8h 41m
Multiple Airlines
Tue 6/168:30 am
MIA
-
ISP
2 stops36h 27m
Multiple Airlines
Deal found 5/20$306
This Southwest deal was found by Cheapflights users on 5/18. 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 7/214:40 pm
ISP
-
MIA
1 stop4h 40m
Southwest
Fri 7/245:25 am
MIA
-
ISP
1 stop5h 05m
Southwest
Deal found 5/18$318
This Southwest deal was found by Cheapflights users on 5/20. 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.
Thu 8/65:00 pm
ISP
-
MIA
1 stop5h 05m
Southwest
Mon 8/106:20 am
MIA
-
ISP
1 stop6h 15m
Southwest
Deal found 5/20$319
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 8/196:05 am
ISP
-
MIA
2 stops9h 25m
Southwest
Sat 8/226:30 am
MIA
-
ISP
1 stop8h 00m
Southwest
Deal found 5/18$320
This Southwest deal was found by Cheapflights users on 5/20. 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.
Fri 8/75:00 pm
ISP
-
MIA
1 stop5h 05m
Southwest
Mon 8/106:20 am
MIA
-
ISP
1 stop6h 15m
Southwest
Deal found 5/20$328
This Southwest deal was found by Cheapflights users on 5/19. 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.
Wed 8/126:05 am
ISP
-
MIA
1 stop4h 50m
Southwest
Wed 8/197:10 am
MIA
-
ISP
1 stop7h 45m
Southwest
Deal found 5/19$333
This Southwest deal was found by Cheapflights users on 5/20. 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.
Sat 6/135:35 pm
ISP
-
MIA
1 stop5h 25m
Southwest
Tue 6/165:50 pm
MIA
-
ISP
1 stop4h 45m
Southwest
Deal found 5/20$338
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/611:00 am
ISP
-
EYW
1 stop24h 25m
Multiple Airlines
Tue 6/91:14 pm
EYW
-
ISP
2 stops22h 03m
Multiple Airlines
Deal found 5/19$370
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 6/58:43 pm
ISP
-
EYW
2 stops38h 42m
Multiple Airlines
Mon 7/61:11 pm
EYW
-
ISP
1 stop5h 50m
Multiple Airlines
Deal found 5/21$484
This Gotogate deal was found by Cheapflights users on 5/19. 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.
Sat 6/611:57 am
ISP
-
EYW
2 stops23h 28m
Breeze Airways
Tue 6/91:14 pm
EYW
-
ISP
2 stops22h 03m
Breeze Airways
Deal found 5/19$773

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 May 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kiwi.com)

One-way from

$136
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$277
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. 15% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 23, 2026.
Use the filters below to find and compare flights from Islip to Florida Keys that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Fri 6/12

9:52 pm-10:06 am

2 stops36h 14m

Key West

Fri 6/19

12:07 pm-8:57 pm

1 stop8h 50m

$287

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 8/19

6:05 am-3:30 pm

2 stops9h 25m

Miami

Sat 8/22

6:30 am-2:30 pm

1 stop8h 00m

$320

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 6/13

2:45 pm-10:05 pm

2 stops7h 20m

Miami

Tue 6/16

5:50 pm-10:35 pm

1 stop4h 45m

$343

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 8/12

6:05 am-3:15 pm

2 stops9h 10m

Miami

Wed 8/19

9:15 am-4:55 pm

2 stops7h 40m

$348

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Sat 6/20

5:15 pm-10:05 pm

1 stop4h 50m

Miami

Mon 6/22

5:25 am-10:30 am

1 stop5h 05m

$357

IslipKey West

ISP - EYW

ISPEYW

Islip Long Island

Sat 6/6

11:00 am-11:25 am

1 stop24h 25m

Key West

Tue 6/9

1:14 pm-11:17 am

2 stops22h 03m

$370
Quickest round-trip

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Wed 6/17

4:40 pm-9:20 pm

1 stop4h 40m

Miami

Sun 6/21

5:35 am-10:05 am

1 stop4h 30m

$374

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Fri 6/19

5:50 pm-11:15 pm

1 stop5h 25m

Miami

Sun 6/21

5:35 am-10:05 am

1 stop4h 30m

$387

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Thu 6/18

3:05 pm-11:15 pm

1 stop8h 10m

Miami

Sun 6/21

5:35 am-10:05 am

1 stop4h 30m

$392

IslipMiami

ISP - MIA

ISPMIA

Islip Long Island

Tue 6/16

2:55 pm-10:10 pm

2 stops7h 15m

Miami

Tue 6/23

6:00 am-1:45 pm

2 stops7h 45m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 33 resultsSorted by cheapest first
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4

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, December is the cheapest month in which you can book a flight from Islip, New York to Florida Keys (average of $29). Flying from Islip, New York to Florida Keys in June is currently the most expensive (average of $342). 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 May 23, 2026.
Read reviews from past customers who have flown Southwest,JetBlue, andFrontier 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
7.9
Good
4,276 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,276 reviews
Southwest
7.9
Good
4,276 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,982 reviews
Southwest
7.9
Good
4,276 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,940 reviews
Southwest
7.9
Good
4,276 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $320, Southwest can have you in Florida Keys from Islip, New York in 9h 25m. 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 $68 and $104 on JetBlue 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, December is the cheapest month in which you can book a flight from Islip, New York to Florida Keys (average of $29). Flying from Islip, New York to Florida Keys in June is currently the most expensive (average of $342). 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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