$44+ Cheap flights from Kissimmee, FL to Florida Keys
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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
May 18 — May 251
Round-trip
1 adult, Economy
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Cheapest flights from Kissimmee to Florida KeysExplore the most affordable flight options available from Kissimmee to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.
Explore the most affordable flight options available from Kissimmee to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Mon 6/810:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 6/1112:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/17![Breeze Airways logo]()
$94
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Wed 5/207:00 am
MIA
- MCO
Nonstop1h 10m
Southwest
Deal found 4/16![Southwest logo]()
$97
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$97
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:55 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Fri 5/11:06 pm
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$99
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:10 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 6/1112:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/2711:10 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$103
This Breeze Airways deal was found by Cheapflights users on 4/12. 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.
Mon 5/1810:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 5/2112:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/12![Breeze Airways logo]()
$104
This Booking.com deal was found by Cheapflights users on 4/14. 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.
Sun 6/2110:10 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 6/2512:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$105
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2210:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 6/2512:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$106
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Thu 5/145:45 pm
MIA
- MCO
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 7/2010:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Fri 7/2412:07 pm
EYW
- MCO
Nonstop1h 15m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$107
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:00 am
MCO
- MIA
Nonstop1h 17m
American Airlines
Mon 5/186:51 am
MIA
- MCO
Nonstop1h 19m
American Airlines
Deal found 4/14![American Airlines logo]()
$117
Best flights from Kissimmee to Florida KeysDiscover carefully curated flight deals from Kissimmee to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 18, 2026.
Discover carefully curated flight deals from Kissimmee to Florida Keys that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 18, 2026.
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1910:20 am
MCO
- MIA
Nonstop1h 10m
Southwest
Wed 5/205:45 pm
MIA
- MCO
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$97
This Breeze Airways deal was found by Cheapflights users on 4/15. 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.
Mon 5/1810:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Thu 5/2112:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$98
This Southwest deal was found by Cheapflights users on 4/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:20 am
MCO
- MIA
Nonstop1h 10m
Southwest
Wed 6/312:35 pm
MIA
- MCO
1 stop6h 25m
Southwest
Deal found 4/12![Southwest logo]()
$107
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Tue 5/1912:10 pm
MIA
- MCO
2 stops7h 30m
Southwest
Deal found 4/15![Southwest logo]()
$112
This Breeze Airways deal was found by Cheapflights users on 4/13. 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 6/2510:10 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Sun 6/2812:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$138
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:50 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Mon 5/116:20 am
MIA
- MCO
Nonstop1h 10m
Southwest
Deal found 4/15![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:30 pm
MCO
- MIA
2 stops6h 10m
Southwest
Sat 5/166:15 am
MIA
- MCO
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$122
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Thu 6/46:20 am
MIA
- MCO
1 stop6h 30m
Southwest
Deal found 4/13![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:10 am
MCO
- MIA
1 stop7h 20m
Southwest
Wed 6/312:10 pm
MIA
- MCO
2 stops7h 30m
Southwest
Deal found 4/15![Southwest logo]()
$132
This Breeze Airways deal was found by Cheapflights users on 4/15. 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 5/2210:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Mon 5/2512:07 pm
EYW
- MCO
Nonstop1h 15m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$208
This American Airlines deal was found by Cheapflights users on 4/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:38 pm
MCO
- EYW
1 stop4h 49m
American Airlines
Wed 9/3012:05 pm
EYW
- MCO
1 stop4h 38m
American Airlines
Deal found 4/17![American Airlines logo]()
$471
This Breeze Airways deal was found by Cheapflights users on 4/16. 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 7/2310:10 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Sun 7/2612:05 pm
EYW
- MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$208
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:50 pm
MCO
- MIA
Nonstop1h 15m
Southwest
Tue 6/96:00 am
MIA
- MCO
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 4/13. 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 4/287:00 am
MCO
- EYW
2 stops12h 40m
Delta
Tue 5/56:23 pm
EYW
- MCO
2 stops14h 29m
Delta
Deal found 4/13![Delta logo]()
$528
This Breeze Airways deal was found by Cheapflights users on 4/14. 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 5/111:10 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Sun 5/39:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$238
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:20 am
MCO
- MIA
Nonstop1h 10m
Southwest
Wed 5/63:00 pm
MIA
- MCO
1 stop7h 10m
Southwest
Deal found 4/13![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:00 am
MCO
- MIA
1 stop5h 55m
Southwest
Sat 5/165:20 pm
MIA
- MCO
Nonstop1h 15m
Southwest
Deal found 4/16![Southwest logo]()
$203
This Delta deal was found by Cheapflights users on 4/13. 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 4/287:59 pm
MCO
- EYW
1 stop19h 38m
Delta
Fri 5/11:22 pm
EYW
- MCO
1 stop20h 34m
Delta
Deal found 4/13![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 4/13. 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 4/287:00 am
MCO
- EYW
2 stops12h 40m
Delta
Sat 5/27:33 am
EYW
- MCO
2 stops13h 45m
Delta
Deal found 4/13![Delta logo]()
$564
Last-minute flights from Kissimmee to Florida KeysDiscover last-minute flight deals from Kissimmee to Florida Keys. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Florida Keys. Data last updated April 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/167:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/239:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Sun 4/197:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/239:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$107
This Breeze Airways deal was found by Cheapflights users on 4/13. 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.
Mon 4/2011:10 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Fri 4/241:06 pm
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$109
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$96
This Breeze Airways deal was found by Cheapflights users on 4/16. 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 4/237:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Mon 4/271:06 pm
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$114
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$97
This Breeze Airways deal was found by Cheapflights users on 4/17. 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.
Sun 4/267:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Mon 4/271:06 pm
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/17![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/2711:10 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$103
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:55 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Fri 5/11:06 pm
EYW
- MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$99
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Wed 5/207:00 am
MIA
- MCO
Nonstop1h 10m
Southwest
Deal found 4/16![Southwest logo]()
$97
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Thu 5/145:45 pm
MIA
- MCO
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$107
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/149:00 am
MCO
- MIA
Nonstop1h 17m
American Airlines
Mon 5/186:51 am
MIA
- MCO
Nonstop1h 19m
American Airlines
Deal found 4/14![American Airlines logo]()
$117
One-way flights from Kissimmee to Florida KeysSearch for one-way flight options from Kissimmee to Florida Keys. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
Search for one-way flight options from Kissimmee to Florida Keys. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Booking.com deal was found by Cheapflights users on 4/14. 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.
Sun 5/37:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$44
This Booking.com deal was found by Cheapflights users on 4/14. 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.
Sun 4/267:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$48
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:45 pm
MCO
- MIA
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$49
This Booking.com deal was found by Cheapflights users on 4/17. 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.
Fri 8/1410:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/17![Breeze Airways logo]()
$49
This Booking.com deal was found by Cheapflights users on 4/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/237:50 am
MCO
- EYW
Nonstop1h 16m
Breeze Airways
Deal found 4/15![Breeze Airways logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/2910:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$55
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Sat 5/211:18 am
MCO
- MIA
1 stop4h 46m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$58
This Booking.com deal was found by Cheapflights users on 4/14. 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.
Fri 5/2210:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$59
This Mytrip deal was found by Cheapflights users on 4/17. 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 5/810:12 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/17![Breeze Airways logo]()
$61
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:18 am
MCO
- MIA
1 stop11h 13m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$63
This Booking.com deal was found by Cheapflights users on 4/17. 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.
Sun 5/1710:10 am
MCO
- EYW
Nonstop1h 15m
Breeze Airways
Deal found 4/17![Breeze Airways logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 4/12. 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.
Sat 5/25:05 am
MCO
- MIA
1 stop9h 32m
Frontier
Deal found 4/12![Frontier logo]()
$65
Find flight deals from Kissimmee to Florida Keys
Keep the following information in mind while searching for Kissimmee to Florida Keys flight deals. Data was last updated April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $94 (Mytrip) |
One-way from | $44 (Booking.com) |
Popular in | June |
Cheapest in | September |
Average price | $178 |
Cheapflights Fare Finder
Customize your flight search to find flights from Kissimmee to Florida Keys 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 18, 2026.
Use the filters below to find and compare flights from Kissimmee to Florida Keys that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Tue 5/19
10:20 am-11:30 am
Nonstop1h 10m
Miami
Wed 5/20
5:45 pm-7:00 pm
Nonstop1h 15m
$97
OrlandoKey West
MCO - EYW
MCOEYW
Orlando
Mon 5/18
10:12 am-11:27 am
Nonstop1h 15m
Key West
Thu 5/21
12:05 pm-1:21 pm
Nonstop1h 16m
$98
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Wed 5/27
10:20 am-11:30 am
Nonstop1h 10m
Miami
Wed 6/3
12:35 pm-7:00 pm
1 stop6h 25m
$107
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Tue 5/12
8:45 pm-9:55 pm
Nonstop1h 10m
Miami
Tue 5/19
12:10 pm-7:40 pm
2 stops7h 30m
$112
Quickest round-trip
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Thu 5/7
8:50 pm-10:00 pm
Nonstop1h 10m
Miami
Mon 5/11
6:20 am-7:30 am
Nonstop1h 10m
$117
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Wed 5/13
2:30 pm-8:40 pm
2 stops6h 10m
Miami
Sat 5/16
6:15 am-7:25 am
Nonstop1h 10m
$122
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Thu 5/28
8:50 pm-10:00 pm
Nonstop1h 10m
Miami
Thu 6/4
6:20 am-12:50 pm
1 stop6h 30m
$127
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Mon 6/1
7:10 am-2:30 pm
1 stop7h 20m
Miami
Wed 6/3
12:10 pm-7:40 pm
2 stops7h 30m
$132
OrlandoKey West
MCO - EYW
MCOEYW
Orlando
Thu 6/25
10:10 am-11:25 am
Nonstop1h 15m
Key West
Sun 6/28
12:05 pm-1:21 pm
Nonstop1h 16m
$138
OrlandoMiami
MCO - MIA
MCOMIA
Orlando
Fri 6/5
8:50 pm-10:05 pm
Nonstop1h 15m
Miami
Tue 6/9
6:00 am-7:15 am
Nonstop1h 15m
$147
Showing 1-10 of 34 resultsSorted by cheapest first
Best time to book a flight from Kissimmee to Florida Keys
Have a flexible travel schedule? Discover the best time to fly to Florida Keys from Kissimmee with our price prediction graph.
MCO-EYW
MCO-MIA
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 Kissimmee to Florida Keys
K1S-zzEOA
MCO-EYW
MCO-MIA
What is the cheapest time of day to fly from K1S to EOA?
Find hourly flight availability from Kissimmee to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 18, 2026.
One of the essential ways to save on airfare from Kissimmee to Florida Keys is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.
Reviews of airlines servicing Florida Keys
Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated April 18, 2026.
Read reviews from past customers who have flown Breeze Airways,Southwest, andJetBlue from Kissimmee to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Overall
8.1
Entertainment
6.6
Food
6.6
Crew
8.7
Comfort
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Kissimmee to Florida Keys. 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 Kissimmee to Florida Keys
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Complete your trip
Complete your trip to Florida Keys by adding a car rental and/or hotel reservation to your travel itinerary.
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Kissimmee and Florida Keys flights
Browse other Kissimmee and Florida Keys flight options. Last updated on April 18, 2026.
Popular flight searches
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Find a return flight route from Florida Keys
Find the right flight back to Kissimmee after your stay in Florida Keys
Kissimmee to Florida Keys flights
Consider these flights traveling from Kissimmee to Florida Keys.
Top 5 airlines flying from Kissimmee to Florida Keys
Discover the top 5 airlines that operate flights from Kissimmee to Florida Keys. 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$99 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$65 | Average$201 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$66 | Average$76 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$89 | Average$157 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$200 | Average$447 | FlexibilityNo cancel fee | On-time71% |