HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/21. 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 9/312:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Sun 9/610:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/21$97
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Sun 8/2310:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/23$98
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/712:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Sun 8/2310:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/19$103
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Sun 8/3010:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/23$104
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/612:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Mon 8/1010:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/19$112
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/712:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Mon 8/1010:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/19$117
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3112:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Sun 8/210:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Deal found 7/23$119
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:59 am
EYW
-
MCO
Nonstop1h 18m
Breeze Airways
Mon 9/288:56 am
MCO
-
EYW
Nonstop1h 23m
Breeze Airways
Deal found 7/23$128
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 9/1810:59 am
EYW
-
MCO
Nonstop1h 18m
Breeze Airways
Mon 9/218:56 am
MCO
-
EYW
Nonstop1h 23m
Breeze Airways
Deal found 7/20$137
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:04 am
EYW
-
MCO
2 stops8h 56m
Multiple Airlines
Sun 8/3010:10 am
MCO
-
EYW
Nonstop1h 15m
Multiple Airlines
Deal found 7/23$144

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 July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Kiwi.com)

One-way from

$49
(Breeze Airways)

Popular in

July

Cheapest in

May

Average price

$253
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. 13% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 23, 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

Sun 10/18

10:59 am-12:17 pm

Nonstop1h 18m

Orlando

Thu 10/22

8:56 am-10:19 am

Nonstop1h 23m

$218

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sat 10/10

10:04 am-5:10 pm

2 stops7h 06m

Orlando

Sun 10/11

8:56 am-10:19 am

Nonstop1h 23m

$314

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 11/13

12:59 pm-11:28 am

2 stops22h 29m

Orlando

Mon 11/23

8:56 am-10:19 am

Nonstop1h 23m

$523

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 9/3

11:30 am-7:17 pm

1 stop7h 47m

Orlando

Sun 9/6

8:07 am-7:39 pm

2 stops11h 32m

$572

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Wed 8/12

10:15 am-6:17 pm

1 stop8h 02m

Orlando

Wed 8/19

7:21 am-7:39 pm

2 stops12h 18m

$578

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 8/16

12:05 pm-1:21 pm

Nonstop1h 16m

Orlando

Wed 8/19

7:27 pm-7:13 pm

3 stops23h 46m

$624

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sat 11/14

10:04 am-8:33 am

3 stops22h 29m

Orlando

Mon 11/23

4:05 pm-12:36 pm

2 stops20h 31m

$807

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 11/13

2:55 pm-6:10 pm

1 stop27h 15m

Orlando

Mon 11/23

7:16 pm-1:59 pm

2 stops18h 43m

$859
Cheapest one-way
Quickest one-way

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 8/31

12:07 pm-1:22 pm

Nonstop1h 15m

$49

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 9/10

10:59 am-12:17 pm

Nonstop1h 18m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 18 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 July 23, 2026.

A simple way to save on the total cost of your ticket is to fly from Key West to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight in the afternoon.

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

Airfare is below average for this route at the moment.
Key West to Kissimmee flights typically cost between $160 and $230 in September.
The cheapest round-trip price found within the last 5 days was $97 on Breeze Airways (Sep 3-Sep 6).

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 18, 2026.

Travelers seeking maximum savings on their Key West to Kissimmee flight should consider departing on Friday afternoons 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 23, 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
8.2
Very good
300 reviews

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Entertainment

6.7

Boarding

8.3

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
8.2
Very good
300 reviews
Breeze Airways
8.2
Very good
300 reviews

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Entertainment

6.7

Boarding

8.3

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. 2 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 18m. Airlines will cover a distance of 269 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $171, our data indicates the cheapest price to be $64. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Key West to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Tampa to Miami flights
Pensacola to Orlando flights
Orlando to Miami flights
Tampa to Fort Lauderdale flights
Fort Lauderdale to Tampa flights
Orlando to Key West flights
Miami to Orlando flights
Tampa to Key West flights
Jacksonville to Miami flights
Miami to Tampa flights
Fort Lauderdale to Orlando flights
Pensacola to Miami flights
Miami to Jacksonville flights
Orlando to Pensacola flights
Pensacola to Tampa flights
Jacksonville to Fort Lauderdale flights
Fort Lauderdale to Jacksonville flights
Fort Lauderdale to Pensacola flights
Pensacola to Fort Lauderdale flights
Orlando to Fort Lauderdale flights
Tallahassee to Fort Lauderdale flights
Tampa to Pensacola flights
Miami to Pensacola flights
Miami to Tallahassee flights
Jacksonville to Key West flights
West Palm Beach to Tampa flights
Miami to Key West flights
West Palm Beach to Tallahassee flights
Fort Lauderdale to Panama City flights
Valparaiso to Miami flights
Tampa to Orlando flights
Pensacola to Key West flights
Fort Lauderdale to Miami flights
Miami to Panama City flights
Sarasota to Miami flights
Tampa to West Palm Beach flights
West Palm Beach to Panama City flights
Pensacola to Jacksonville flights
Orlando to Panama City flights
West Palm Beach to Jacksonville flights
West Palm Beach to Pensacola flights
Tallahassee to Miami flights
Jacksonville to West Palm Beach flights
Jacksonville to Pensacola flights
Sarasota to Fort Lauderdale flights
Gainesville to Miami flights
Fort Lauderdale to Tallahassee flights
Fort Lauderdale to Key West flights
Orlando to Jacksonville flights
Tampa to Valparaiso flights

Top 2 airlines flying from Key West to Kissimmee

Discover the top 2 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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$84FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$81Average$144FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights