$49+ Cheap flights from Key West (EYW) to Kissimmee, FL
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Oct 11 — Oct 181
Round-trip
1 adult, Economy
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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
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Cheapest flights from Key West to KissimmeeExplore 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 September 11, 2026.
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 September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2910:59 am -
Nonstop1h 18m
Sun 11/18:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 -
Nonstop1h 18m
Sun 9/208:56 am -
Nonstop1h 23m
Deal found 9/10![Breeze Airways logo]()
$107
This Breeze Airways deal was found by Cheapflights users on 9/7. 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 12/1110:59 am -
Nonstop1h 18m
Mon 12/148:56 am -
Nonstop1h 23m
Deal found 9/7![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1110:59 am -
Nonstop1h 18m
Sun 9/138:56 am -
Nonstop1h 23m
Deal found 9/7![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2310:59 am -
Nonstop1h 18m
Sun 10/258:56 am -
Nonstop1h 23m
Deal found 9/6![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/2410:59 am -
Nonstop1h 18m
Mon 9/288:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/910:59 am -
Nonstop1h 18m
Mon 10/128:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$127
This Breeze Airways deal was found by Cheapflights users on 9/8. 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 9/1110:59 am -
Nonstop1h 18m
Mon 9/148:56 am -
Nonstop1h 23m
Deal found 9/8![Breeze Airways logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/1710:59 am -
Nonstop1h 18m
Fri 9/188:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1410:59 am -
Nonstop1h 18m
Mon 9/218:56 am -
Nonstop1h 23m
Deal found 9/7![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1612:59 pm -
2 stops30h 29m
Sun 10/258:56 am -
Nonstop1h 23m
Deal found 9/7![Multiple Airlines logo]()
$148
Best flights from Key West to KissimmeeDiscover carefully curated flight deals from Key West to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
Discover carefully curated flight deals from Key West to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/2110:59 am -
Nonstop1h 18m
Tue 9/225:19 pm -
2 stops16h 05m
Deal found 9/7![Multiple Airlines logo]()
$213
This Gotogate deal was found by Cheapflights users on 9/9. 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.
Mon 11/3010:59 am -
Nonstop1h 18m
Wed 12/28:36 pm -
2 stops14h 45m
Deal found 9/9![Breeze Airways logo]()
$429
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:19 pm -
2 stops14h 59m
Sat 10/37:59 pm -
2 stops14h 47m
Deal found 9/10![Delta logo]()
$591
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:15 pm -
2 stops23h 42m
Mon 9/286:20 pm -
2 stops19h 09m
Deal found 9/9![United Airlines logo]()
$857
This KAYAK deal was found by Cheapflights users on 9/7. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2111:59 am -
1 stop5h 13m
Tue 9/227:10 am -
2 stops26h 14m
Deal found 9/7![Breeze Airways logo]()
$564
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:19 pm -
2 stops14h 59m
Sat 10/37:59 pm -
2 stops14h 47m
Deal found 9/10![Delta logo]()
$610
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:15 pm -
2 stops24h 43m
Mon 10/58:37 pm -
2 stops16h 52m
Deal found 9/8![United Airlines logo]()
$928
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm -
2 stops23h 42m
Tue 9/294:05 pm -
1 stop21h 24m
Deal found 9/10![United Airlines logo]()
$932
Last-minute flights from Key West to KissimmeeDiscover last-minute flight deals from Key West to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1110:59 am -
Nonstop1h 18m
Sun 9/138:56 am -
Nonstop1h 23m
Deal found 9/7![Breeze Airways logo]()
$113
This Breeze Airways deal was found by Cheapflights users on 9/8. 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 9/1110:59 am -
Nonstop1h 18m
Mon 9/148:56 am -
Nonstop1h 23m
Deal found 9/8![Breeze Airways logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/1410:59 am -
Nonstop1h 18m
Mon 9/218:56 am -
Nonstop1h 23m
Deal found 9/7![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/1710:59 am -
Nonstop1h 18m
Fri 9/188:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 -
Nonstop1h 18m
Sun 9/208:56 am -
Nonstop1h 23m
Deal found 9/10![Breeze Airways logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/2410:59 am -
Nonstop1h 18m
Mon 9/288:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/110:59 am -
Nonstop1h 18m
Fri 10/28:56 am -
Nonstop1h 23m
Deal found 9/10![Breeze Airways logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/910:59 am -
Nonstop1h 18m
Mon 10/128:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/1612:59 pm -
2 stops30h 29m
Sun 10/258:56 am -
Nonstop1h 23m
Deal found 9/7![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2310:59 am -
Nonstop1h 18m
Sun 10/258:56 am -
Nonstop1h 23m
Deal found 9/6![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2910:59 am -
Nonstop1h 18m
Sun 11/18:56 am -
Nonstop1h 23m
Deal found 9/9![Breeze Airways logo]()
$103
One-way flights from Key West to KissimmeeSearch for one-way flight options from Key West to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
Search for one-way flight options from Key West to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/10. 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.
Wed 1/2011:19 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$49
This Priceline deal was found by Cheapflights users on 9/7. 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.
Tue 11/2411:04 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/1810:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$54
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 1/2110:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/2210:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$59
This Priceline deal was found by Cheapflights users on 9/7. 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.
Sun 11/2210:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$61
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2510:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Breeze Airways logo]()
$64
This Priceline deal was found by Cheapflights users on 9/7. 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 11/2310:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 2/1810:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 12/1310:59 am -
Nonstop1h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Breeze Airways logo]()
$78
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $103 (Kiwi.com) |
One-way from | $49 (Breeze Airways) |
Popular in | July |
Cheapest in | May |
Average price | $154 |
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 7,457,451 searches. Data last updated September 11, 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
Cheapest round-trip
Quickest round-trip
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Fri 9/25
10:59 am-12:17 pm
Nonstop1h 18m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$53
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Sat 11/7
10:04 am-9:38 pm
2 stops11h 34m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Thu 11/19
10:48 am-8:15 pm
1 stop9h 27m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$152
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Fri 10/9
11:59 am-3:48 pm
2 stops27h 49m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Mon 9/21
10:59 am-12:17 pm
Nonstop1h 18m
Orlando
Tue 9/22
5:19 pm-9:24 am
2 stops16h 05m
$213
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Sun 10/11
12:01 pm-11:29 pm
2 stops11h 28m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$400
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Sat 12/26
8:59 am-7:59 pm
1 stop11h 00m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$429
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Mon 11/30
10:59 am-12:17 pm
Nonstop1h 18m
Orlando
Wed 12/2
8:36 pm-11:21 am
2 stops14h 45m
$429
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Sat 10/10
4:20 pm-7:31 pm
1 stop27h 11m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$439
Key WestOrlando
EYW Key West - MCO Orlando
EYWMCO
Key West
Thu 1/21
3:04 pm-5:24 pm
1 stop26h 20m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$502
Showing 1-10 of 17 resultsSorted by cheapest first
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.
EYW-MCO
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
EYW-K1S
EYW-MCO
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 September 11, 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 31% 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 $132 and $154 in October.The cheapest round-trip price found within the last 5 days was $103 on Breeze Airways (Oct 29-Nov 1).
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 September 5, 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 September 11, 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.
Overall
8.2
Comfort
8.2
Boarding
8.4
Crew
8.8
Entertainment
6.8
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.2
Comfort
8.2
Boarding
8.4
Crew
8.8
Entertainment
6.8
Food
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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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.
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Alternative routes for Key West to Kissimmee
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Key West and Kissimmee flights
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Key West to Kissimmee flights
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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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$76 | Average$80 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$79 | Average$127 | FlexibilityNo cancel fee | On-timeN/A |