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Key West

$59+ Cheap flights from Kissimmee, FL to Key West (EYW)

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in August or January, booked 86 days in advance, depart on a Monday or Tuesday and return on a Sunday

Cheap flight deals from Kissimmee to Key West

Keep the following information in mind while searching for Kissimmee to Key West flight deals. Data was last updated julio 30, 2025.

Round-trip from

$118
(Breeze Airways)

One-way from

$59
(Breeze Airways)

Popular in

July

Cheapest in

August

Average price

$212
From Kissimmee to Key West
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One-way flight from Kissimmee to Key West
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Highest demand for flights based on searches. 4% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Kissimmee to Key West

Cheapest flights from Kissimmee to Key West
Explore the most affordable flight options available from Kissimmee to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/1411:52 amMCO - EYW
Nonstop1h 15mBreeze Airways
lun. 8/1810:02 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 7/28$118
This Mytrip deal was found by Cheapflights users on 7/28. 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.
lun. 8/187:00 amMCO - EYW
1 stop9h 41mMultiple Airlines
vie. 8/2210:33 amEYW - MCO
1 stop10h 24mMultiple Airlines
Deal found 7/28$205
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/271:13 pmMCO - EYW
1 stop5h 54mAmerican Airlines
mié. 9/37:31 pmEYW - MCO
1 stop4h 24mAmerican Airlines
Deal found 7/28$251

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee 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 2,558,603 searches. Data last updated julio 30, 2025.
Use the filters below to find and compare flights from Kissimmee to Key West that are best for you.

Fly from

Kissimmee

Fly to

Key West

Route

Depart

Return

Price

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

jue. 8/14

11:52 am-1:07 pm

Nonstop1h 15m

Key West

lun. 8/18

10:02 am-11:12 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

lun. 8/18

7:00 am-4:41 pm

1 stop9h 41m

Key West

vie. 8/22

10:33 am-8:57 pm

1 stop10h 24m

$205

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

mié. 8/27

1:13 pm-7:07 pm

1 stop5h 54m

Key West

mié. 9/3

7:31 pm-11:55 pm

1 stop4h 24m

$251

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

jue. 9/11

7:00 am-8:15 am

Nonstop1h 15m

$59

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

lun. 8/25

7:00 am-4:51 pm

1 stop9h 51m

$139

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

mar. 9/2

8:01 am-10:53 am

1 stop2h 52m

$194

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

vie. 8/29

4:14 pm-2:14 pm

2 stops22h 00m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Kissimmee to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Kissimmee 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 Kissimmee to Key West

How far ahead should I book a flight from Kissimmee to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Kissimmee to Key West. Price data was last updated on July 25, 2025.

The best time to book flights from Kissimmee to Key West is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Kissimmee to Key West?

Currently, August is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $328). Flying from Kissimmee to Key West in March is currently the most expensive (average of $492). 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.

What is the cheapest time of day to fly from K1S to EYW?

Find hourly flight availability from Kissimmee to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 30, 2025.

When flying from Kissimmee to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Kissimmee to Key West?

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Key West. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kissimmee to Key West flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated julio 30, 2025.
Read through reviews of airlines operating flights from Kissimmee to Key West, such as Breeze Airways, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Food

6.7

Entertainment

6.5

Boarding

8.2

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Food

6.7

Entertainment

6.5

Boarding

8.2

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
8,896 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Food

6.7

Entertainment

6.5

Boarding

8.2

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Food

6.7

Entertainment

6.5

Boarding

8.2

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Key West. 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 into for flights to Key West from Kissimmee?

    If you book a flight to Key West from Kissimmee, you will be flying to Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Kissimmee to Key West per day from 6 different airlines.

  • What are the cheapest airlines to fly from Kissimmee to Key West one-way?

    The cheapest airlines for a one-way flight from Kissimmee to Key West are Breeze Airways ($59), American Airlines ($194), and United Airlines ($259).

  • What are the cheapest flights from Kissimmee to Key West?

    The cheapest flight price from Kissimmee to Key West is $59. On average you can expect to pay $132. The most popular route, (Orlando - Key West), can usually be booked for $118.

  • Can I find deals for flights from Kissimmee to Key West that include hotel bookings?

    Yes. In addition to deals on Kissimmee to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kissimmee to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kissimmee to Key West.

  • Can I find deals for business class flights from Kissimmee to Key West?

    Yes. Cheapflights offers flight deals from Kissimmee to Key West 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 Kissimmee to Key West?

    Currently, August is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $328). Flying from Kissimmee to Key West in March is currently the most expensive (average of $492). 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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Top 6 airlines flying from Kissimmee to Key West

Discover the top 6 airlines that operate flights from Kissimmee to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$170FlexibilityNo cancel feeOn-time88%
Silver AirwaysCheapest$69Average$172FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$81Average$171FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$341FlexibilityNo cancel feeOn-time71%

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