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Kissimmee

$49+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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Cheap 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 December 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/118:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 12/147:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/3$98
This CheapOair deal was found by Cheapflights users on 12/3. 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.
Fri 12/191:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Sun 12/217:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/3$102
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/58:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Mon 12/87:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/2$104
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/188:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Mon 12/2211:15 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/3$105
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Sun 12/148:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Fri 12/1911:15 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/3$107
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Mon 12/158:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Fri 12/1911:15 amMCO - EYW
Nonstop1h 15mBreeze Airways
Deal found 12/3$109
This Expedia deal was found by Cheapflights users on 12/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/221:10 pmEYW - MCO
Nonstop1h 10mMultiple Airlines
Wed 12/246:45 amMCO - EYW
1 stop6h 45mMultiple Airlines
Deal found 12/4$147
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Mon 12/158:55 amEYW - MCO
Nonstop1h 10mMultiple Airlines
Fri 12/196:45 amMCO - EYW
1 stop6h 45mMultiple Airlines
Deal found 12/3$169
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/192:30 pmEYW - MCO
1 stop2h 59mSpirit Airlines
Mon 12/226:45 amMCO - EYW
1 stop6h 45mSpirit Airlines
Deal found 12/3$173
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Sun 12/148:55 amEYW - MCO
Nonstop1h 10mMultiple Airlines
Sat 12/206:45 amMCO - EYW
1 stop6h 45mMultiple Airlines
Deal found 12/3$180
This Expedia deal was found by Cheapflights users on 12/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:10 pmEYW - MCO
Nonstop1h 10mMultiple Airlines
Mon 12/296:45 amMCO - EYW
1 stop6h 45mMultiple Airlines
Deal found 12/4$184
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 12/58:55 amEYW - MCO
Nonstop1h 10mMultiple Airlines
Mon 12/88:25 pmMCO - EYW
2 stops37h 42mMultiple Airlines
Deal found 12/2$190

Find 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 December 5, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$98
(Kiwi.com)

One-way from

$49
(Kiwi.com)

Popular in

May

Cheapest in

July

Average price

$209
Provider with most accurate pricing for Key West-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Orlando (ORL) flights.
Search Deals
From Key West to Kissimmee
Search Deals
One-way flight from Key West to Kissimmee
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($17 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 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 December 5, 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 1/22

10:06 am-11:26 am

Nonstop1h 20m

Orlando

Sun 1/25

8:10 am-9:26 am

Nonstop1h 16m

$98

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 12/19

1:10 pm-2:20 pm

Nonstop1h 10m

Orlando

Mon 12/22

11:15 am-12:30 pm

Nonstop1h 15m

$102

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 12/19

1:10 pm-2:20 pm

Nonstop1h 10m

Orlando

Sun 12/21

7:00 am-8:15 am

Nonstop1h 15m

$102

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 12/26

1:10 pm-2:20 pm

Nonstop1h 10m

Orlando

Sun 12/28

7:00 am-8:15 am

Nonstop1h 15m

$102

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 12/18

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Mon 12/22

11:15 am-12:30 pm

Nonstop1h 15m

$105

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 12/15

8:55 am-10:05 am

Nonstop1h 10m

Orlando

Fri 12/19

11:15 am-12:30 pm

Nonstop1h 15m

$109

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 1/1

12:20 pm-5:29 pm

1 stop5h 09m

Orlando

Thu 1/8

8:10 am-9:26 am

Nonstop1h 16m

$123

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 12/22

1:10 pm-2:20 pm

Nonstop1h 10m

Orlando

Wed 12/24

6:45 am-1:30 pm

1 stop6h 45m

$147

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 1/22

10:06 am-11:26 am

Nonstop1h 20m

Orlando

Sun 1/25

6:00 am-11:56 am

1 stop5h 56m

$157

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Tue 1/6

12:20 pm-5:29 pm

1 stop5h 09m

Orlando

Wed 1/7

6:45 am-1:30 pm

1 stop6h 45m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

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, November is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $79). Flying from Key West to Kissimmee in October is currently the most expensive (average of $118). 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 December 5, 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 November 29, 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. Monday at noon 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 December 5, 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
8.2
Very good
242 reviews

Food

6.7

Boarding

8.4

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
242 reviews
Breeze Airways
8.2
Very good
242 reviews

Food

6.7

Boarding

8.4

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
United Airlines
7.4
Good
9,064 reviews
Breeze Airways
8.2
Very good
242 reviews

Food

6.7

Boarding

8.4

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
American Airlines
7.2
Good
11,047 reviews
Breeze Airways
8.2
Very good
242 reviews

Food

6.7

Boarding

8.4

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Silver Airways
5.7
Fair
237 reviews
Breeze Airways
8.2
Very good
242 reviews

Food

6.7

Boarding

8.4

Comfort

8.2

Overall

8.2

Crew

8.8

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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 20m. 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 $46. Users have also found prices from $64 and $86 on United Airlines and Silver Airways, 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 $107, our data indicates the cheapest price to be $49. The most popular route (Key West - Orlando), is priced around $98.

  • 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, November is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $79). Flying from Key West to Kissimmee in October is currently the most expensive (average of $118). 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 December 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$50Average$88FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$101Average$146FlexibilityNo cancel feeOn-timeN/A
Silver AirwaysCheapest$121Average$177FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$221Average$596FlexibilityNo cancel feeOn-time71%

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