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Kissimmee

$61+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(Breeze Airways)

One-way from

$61
(Priceline)

Popular in

May

Cheapest in

July

Average price

$172
Provider with most accurate pricing for Key West-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Key West-Orlando (ORL) flights.
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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. 18% potential increase in price ($44 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 October 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 October 16, 2025.

This Breeze Airways deal was found by Cheapflights users on 10/16. 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 11/138:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 11/167:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/16$118
This Priceline deal was found by Cheapflights users on 10/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 12/147:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$122
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 10/318:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Mon 11/37:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$126
This CheapOair deal was found by Cheapflights users on 10/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Mon 11/37:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$128
This Breeze Airways deal was found by Cheapflights users on 10/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 10/267:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$138
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 10/238:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 10/267:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$145
This Priceline deal was found by Cheapflights users on 10/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1112:20 pmEYW - MCO
1 stop5h 09mMultiple Airlines
Sun 12/147:00 amMCO - EYW
Nonstop1h 15mMultiple Airlines
Deal found 10/15$151
This Kissandfly.com deal was found by Cheapflights users on 10/16. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 11/27:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/16$159
This Priceline deal was found by Cheapflights users on 10/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 11/167:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/15$160
This Breeze Airways deal was found by Cheapflights users on 10/16. 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.
Fri 10/178:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 10/197:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 10/16$168

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 October 16, 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 11/13

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Sun 11/16

7:00 am-8:15 am

Nonstop1h 15m

$118

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 12/11

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Sun 12/14

7:00 am-8:15 am

Nonstop1h 15m

$122

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 11/3

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Thu 11/6

7:00 am-8:15 am

Nonstop1h 15m

$122

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 11/9

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Sun 11/16

7:00 am-8:15 am

Nonstop1h 15m

$128

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 11/28

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Fri 12/5

7:00 am-8:15 am

Nonstop1h 15m

$129

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 12/11

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Fri 12/12

7:00 am-8:15 am

Nonstop1h 15m

$148

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 11/9

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Sun 11/16

6:30 am-11:20 am

1 stop4h 50m

$162

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 3/27

1:06 pm-2:26 pm

Nonstop1h 20m

Orlando

Mon 3/30

11:10 am-12:26 pm

Nonstop1h 16m

$176

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 11/20

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Sun 11/23

6:45 am-11:20 am

1 stop4h 35m

$178

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 11/3

11:11 am-4:52 pm

1 stop5h 41m

Orlando

Thu 11/6

7:00 am-8:15 am

Nonstop1h 15m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 20 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, March is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $81). Flying from Key West to Kissimmee in January is currently the most expensive (average of $114). 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 October 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Key West to Kissimmee in the afternoon. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight in the morning.

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 October 12, 2025.

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

How much does it cost to fly round-trip from Key West to Kissimmee?

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 October 16, 2025.
See what other customers who have flown with Breeze Airways, United Airlines, and American Airlines 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
8.1
Very good
217 reviews

Comfort

8.2

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

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
8.1
Very good
217 reviews
Breeze Airways
8.1
Very good
217 reviews

Comfort

8.2

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

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
8,982 reviews
Breeze Airways
8.1
Very good
217 reviews

Comfort

8.2

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

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
11,040 reviews
Breeze Airways
8.1
Very good
217 reviews

Comfort

8.2

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

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!
Silver Airways
5.8
Fair
240 reviews
Breeze Airways
8.1
Very good
217 reviews

Comfort

8.2

Entertainment

6.6

Overall

8.1

Boarding

8.3

Food

6.7

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 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.

  • How long is the flight from Key West to Kissimmee?

    Departing from Key West to Kissimmee will take you 1h 10m. Airlines will cover a distance of 269 mi. Most flights are nonstop.

  • 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 $82. Users have also found prices from $232 and $242 on Spirit Airlines and American Airlines, 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 $115, our data indicates the cheapest price to be $61. 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, March is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $81). Flying from Key West to Kissimmee in January is currently the most expensive (average of $114). 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$84FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$101Average$166FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$119Average$177FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$221Average$550FlexibilityNo cancel feeOn-time71%

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