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Kissimmee

$41+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
May 27 — Jun 31
Wed 5/27
Wed 6/3
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 April 27, 2026.

This Gotogate deal was found by Cheapflights users on 4/24. 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.
Thu 5/712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Sun 5/1010:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/24$87
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Mon 5/411:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/26$97
This Breeze Airways deal was found by Cheapflights users on 4/23. 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 5/812:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Sun 5/1010:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/23$98
This Mytrip deal was found by Cheapflights users on 4/25. 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.
Fri 6/512:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Fri 6/1210:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/25$102
This Mytrip deal was found by Cheapflights users on 4/27. 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.
Thu 6/2512:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Mon 6/2910:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/27$104
This Mytrip deal was found by Cheapflights users on 4/26. 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.
Fri 5/11:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Sun 5/37:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/26$107
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Fri 5/810:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/26$108
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Mon 6/110:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/26$110
This Mytrip deal was found by Cheapflights users on 4/24. 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.
Sun 5/1012:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Sun 5/1710:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/24$113
This CheapOair deal was found by Cheapflights users on 4/24. 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 5/11:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Mon 5/411:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/24$114

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$87
(Gotogate)

One-way from

$41
(Mytrip)

Popular in

May

Cheapest in

November

Average price

$188
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. 34% potential increase in price ($94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 19% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 27, 2026.
Use the filters below to find and compare flights from Key West to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 5/8

12:07 pm-1:22 pm

Nonstop1h 15m

Orlando

Sun 5/10

10:10 am-11:25 am

Nonstop1h 15m

$98

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 5/7

12:05 pm-1:21 pm

Nonstop1h 16m

Orlando

Sun 5/10

10:10 am-11:25 am

Nonstop1h 15m

$98

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 7/3

12:07 pm-1:22 pm

Nonstop1h 15m

Orlando

Sun 7/5

10:10 am-11:25 am

Nonstop1h 15m

$108

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 6/7

12:05 pm-1:21 pm

Nonstop1h 16m

Orlando

Mon 6/8

11:39 am-12:34 pm

3 stops24h 55m

$698

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 5/28

2:26 pm-2:43 pm

2 stops24h 17m

Orlando

Mon 6/1

3:05 pm-1:30 pm

2 stops22h 25m

$701

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 5/14

4:47 pm-8:12 pm

1 stop27h 25m

Orlando

Sun 5/17

6:10 pm-3:07 pm

1 stop20h 57m

$780
Cheapest one-way

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 8/13

12:05 pm-1:21 pm

Nonstop1h 16m

$53
Quickest one-way

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 6/1

12:07 pm-1:22 pm

Nonstop1h 15m

$93

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Wed 5/13

11:46 am-9:47 pm

2 stops10h 01m

$118

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 5/17

12:05 pm-1:21 pm

Nonstop1h 16m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 17 resultsSorted by cheapest first
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 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 April 27, 2026.

A simple way to save on the total cost of your ticket is to fly from Key West to Kissimmee in the morning. If you’re flexible enough to do this you can expect to save up to 22% on your trip compared to booking a flight in the afternoon.

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 April 18, 2026.

Travelers seeking maximum savings on their Key West to Kissimmee flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday 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 April 27, 2026.
See what other customers who have flown with Breeze Airways 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
281 reviews

Crew

8.7

Comfort

8.2

Boarding

8.3

Food

6.6

Entertainment

6.6

Overall

8.1

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.1
Very good
281 reviews
Breeze Airways
8.1
Very good
281 reviews

Crew

8.7

Comfort

8.2

Boarding

8.3

Food

6.6

Entertainment

6.6

Overall

8.1

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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. 4 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 15m. Airlines will cover a distance of 269 mi. Most flights are nonstop.

  • 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 $114, our data indicates the cheapest price to be $47. The most popular route (Key West - Orlando), is priced around $97.

  • 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.

See more FAQs

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Top 4 airlines flying from Key West to Kissimmee

Discover the top 4 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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Silver AirwaysCheapest$76Average$176FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$77Average$94FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$81Average$138FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$87Average$181FlexibilityNo cancel feeOn-time69%

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