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Kissimmee

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

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Key West to Kissimmee

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

Round-trip from

$118
(Breeze Airways)

One-way from

$59
(Breeze Airways)

Popular in

May

Cheapest in

June

Average price

$137
From Key West to Kissimmee
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One-way flight from Key West to Kissimmee
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Highest demand for flights based on searches. 17% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($17 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 Key West to Kissimmee

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

This Breeze Airways deal was found by Cheapflights users on 7/29. 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.
Thu 8/2810:02 amEYW - MCO
Nonstop1h 10mBreeze Airways
Thu 9/47:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 7/29$118
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Mon 12/88:47 amEYW - MCO
Nonstop1h 10mMultiple Airlines
Fri 12/126:55 amMCO - EYW
1 stop6h 35mMultiple Airlines
Deal found 7/29$242
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Mon 12/82:25 pmEYW - MCO
2 stops17h 35mSpirit Airlines
Fri 12/126:55 amMCO - EYW
1 stop6h 35mSpirit Airlines
Deal found 7/29$330
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 8/301:41 pmEYW - MCO
1 stop6h 39mAmerican Airlines
Mon 9/18:35 pmMCO - EYW
1 stop14h 18mAmerican Airlines
Deal found 7/29$405

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Kissimmee 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 July 30, 2025.
Use the filters below to find and compare flights from Key West to Kissimmee that are best for you.

Fly from

Key West

Fly to

Kissimmee

Route

Depart

Return

Price

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 8/28

10:02 am-11:12 am

Nonstop1h 10m

Orlando

Thu 9/4

7:00 am-8:15 am

Nonstop1h 15m

$118

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 12/8

8:47 am-9:57 am

Nonstop1h 10m

Orlando

Fri 12/12

6:55 am-1:30 pm

1 stop6h 35m

$242

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 12/8

2:25 pm-8:00 am

2 stops17h 35m

Orlando

Fri 12/12

6:55 am-1:30 pm

1 stop6h 35m

$330

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sat 8/30

1:41 pm-8:20 pm

1 stop6h 39m

Orlando

Mon 9/1

8:35 pm-10:53 am

1 stop14h 18m

$405

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 8/28

10:02 am-11:12 am

Nonstop1h 10m

$59

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 8/22

10:33 am-8:57 pm

1 stop10h 24m

$99

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sat 11/1

12:40 pm-10:56 pm

1 stop10h 16m

$122

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 8/28

4:36 pm-8:02 am

1 stop15h 26m

$171

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Wed 8/20

7:40 pm-11:43 pm

1 stop4h 03m

$194

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 11/6

2:25 pm-12:31 pm

3 stops22h 06m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 11 results
1
2

Best time to book a flight from Key West to Kissimmee

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

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

Currently, May is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $206). Flying from Key West to Kissimmee in November is currently the most expensive (average of $288). 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 EYW to K1S?

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

When flying from Key West to Kissimmee, 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 Key West to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Key West to Kissimmee. Price data was last updated on July 27, 2025.

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

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated July 30, 2025.
See what other customers who have flown with Breeze Airways, United Airlines, and JetBlue from Key West to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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!
JetBlue
7.3
Good
2,913 reviews
Breeze Airways
8.0
Very good
191 reviews

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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!
Allegiant Air
7.2
Good
703 reviews
Breeze Airways
8.0
Very good
191 reviews

Food

6.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.0

Entertainment

6.5

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 Key West to Kissimmee. 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 Key West to Kissimmee?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Key West to Kissimmee. 5 airlines have flights from Key West to Kissimmee on a regular basis. Booking flights from Key West to Kissimmee should not be difficult; the airport handles an average of 0 outbound flights to Kissimmee per day.

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

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $59. Users have also found prices from $171 and $189 on Allegiant Air and JetBlue, respectively.

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

    Looking for the cheapest flight from Key West to Kissimmee? While on average our users pay $118, our data indicates the cheapest price to be $59. The most popular route (Key West - Orlando), is priced around $118.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $206). Flying from Key West to Kissimmee in November is currently the most expensive (average of $288). 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 5 airlines flying from Key West to Kissimmee

Discover the top 5 airlines that operate flights from Key West to Kissimmee. 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$82FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$87Average$253FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$105Average$181FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$221Average$518FlexibilityNo cancel feeOn-time71%

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