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Florida Keys

$48+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$95
(Southwest)

One-way from

$48
(Southwest)

Popular in

December

Cheapest in

September

Average price

$127
From Kissimmee to Florida Keys
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One-way flight from Kissimmee to Florida Keys
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Highest demand for flights based on searches. 15% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Kissimmee to Florida Keys

Cheapest flights from Kissimmee to Florida Keys
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 September 11, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:00 amMCO - MIA
Nonstop1h 15mSouthwest
Wed 10/156:55 amMIA - MCO
Nonstop1h 10mSouthwest
Deal found 9/10$95
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:40 pmMCO - MIA
Nonstop1h 15mSouthwest
Tue 10/145:30 pmMIA - MCO
Nonstop1h 10mSouthwest
Deal found 9/9$99
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/88:40 pmMCO - MIA
Nonstop1h 15mSouthwest
Wed 10/155:30 pmMIA - MCO
Nonstop1h 10mSouthwest
Deal found 9/9$100
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 11/46:00 amMCO - MIA
Nonstop1h 12mAmerican Airlines
Wed 11/127:10 pmMIA - MCO
Nonstop1h 15mAmerican Airlines
Deal found 9/11$103
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:35 pmMCO - MIA
Nonstop1h 11mAmerican Airlines
Sat 11/15:22 pmMIA - MCO
Nonstop1h 06mAmerican Airlines
Deal found 9/10$104
This Southwest deal was found by Cheapflights users on 9/11. 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 10/288:40 pmMCO - MIA
Nonstop1h 15mSouthwest
Wed 10/293:15 pmMIA - MCO
1 stop4h 55mSouthwest
Deal found 9/11$105
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/188:35 pmMCO - MIA
Nonstop1h 15mSouthwest
Tue 10/214:35 pmMIA - MCO
1 stop6h 45mSouthwest
Deal found 9/10$109
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/118:35 pmMCO - MIA
Nonstop1h 11mAmerican Airlines
Mon 10/137:00 amMIA - MCO
Nonstop1h 08mAmerican Airlines
Deal found 9/10$111
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/412:30 pmMCO - MIA
Nonstop1h 14mAmerican Airlines
Mon 10/610:54 pmMIA - MCO
Nonstop1h 05mAmerican Airlines
Deal found 9/11$112
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 10/188:35 pmMCO - MIA
Nonstop1h 15mSouthwest
Sat 10/256:00 amMIA - MCO
1 stop5h 40mSouthwest
Deal found 9/11$113
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/98:58 amMCO - MIA
Nonstop1h 14mAmerican Airlines
Tue 10/149:15 amMIA - MCO
Nonstop1h 05mAmerican Airlines
Deal found 9/10$115
This Breeze Airways deal was found by Cheapflights users on 9/11. 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 10/57:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 10/98:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 9/11$118

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 September 11, 2025.
Use the filters below to find and compare flights from Kissimmee to Florida Keys that are best for you.

Fly from

Kissimmee

Fly to

Florida Keys

Route

Depart

Return

Price

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 10/28

8:40 pm-9:55 pm

Nonstop1h 15m

Miami

Wed 10/29

5:30 pm-6:40 pm

Nonstop1h 10m

$95

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Wed 10/8

8:40 pm-9:55 pm

Nonstop1h 15m

Miami

Wed 10/15

5:30 pm-6:40 pm

Nonstop1h 10m

$100

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sat 10/18

8:35 pm-9:50 pm

Nonstop1h 15m

Miami

Sat 10/25

5:25 pm-6:35 pm

Nonstop1h 10m

$103

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Wed 10/29

8:40 pm-9:55 pm

Nonstop1h 15m

Miami

Tue 11/4

7:40 am-2:00 pm

1 stop6h 20m

$105

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sat 10/18

8:35 pm-9:50 pm

Nonstop1h 15m

Miami

Tue 10/21

4:35 pm-11:20 pm

1 stop6h 45m

$109

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Fri 10/10

7:15 am-8:31 am

Nonstop1h 16m

Miami

Wed 10/15

7:50 pm-9:04 pm

Nonstop1h 14m

$117

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 11/2

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 11/9

8:55 am-10:05 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 10/20

7:00 am-8:15 am

Nonstop1h 15m

Key West

Fri 10/24

8:55 am-10:05 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 9/28

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 10/2

8:55 am-10:05 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 11/10

7:00 am-8:15 am

Nonstop1h 15m

Key West

Fri 11/14

8:55 am-10:05 am

Nonstop1h 10m

$118

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 39 results
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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.
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

What is the cheapest month to book a flight from Kissimmee to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $328). Flying from Kissimmee to Florida Keys in March is currently the most expensive (average of $491). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from 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 September 11, 2025.

When flying from Kissimmee to Florida Keys, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 11, 2025.
Read reviews from past customers who have flown Breeze Airways, United Airlines, and American Airlines 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.
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
205 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
8,937 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
JetBlue
7.2
Good
2,913 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Silver Airways
5.8
Fair
242 reviews
Breeze Airways
8.0
Very good
205 reviews

Boarding

8.2

Entertainment

6.5

Comfort

8.1

Food

6.7

Crew

8.7

Overall

8.0

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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.

  • How long is the flight from Kissimmee to Florida Keys?

    For as low as $95, Southwest can have you in Florida Keys from Kissimmee in 1h 15m. The distance from Kissimmee to Florida Keys is about 192 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Kissimmee to Florida Keys one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $48. However, be on the lookout for offers from Breeze Airways and Spirit Airlines, as they are both options that can get you from Kissimmee to Florida Keys for a low price.

  • What are the cheapest flights from Kissimmee to Florida Keys?

    The cheapest flight price from Kissimmee to Florida Keys is $59. On average you can expect to pay $108. The most popular route, (Orlando - Miami), can usually be booked for $95.

  • Can I find deals for flights from Kissimmee to Florida Keys that include hotel bookings?

    Yes. In addition to deals on Kissimmee to Florida Keys flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kissimmee to Florida Keys?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kissimmee to Florida Keys.

  • Can I find deals for business class flights from Kissimmee to Florida Keys?

    Yes. Cheapflights offers flight deals from Kissimmee to Florida Keys by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kissimmee to Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $328). Flying from Kissimmee to Florida Keys in March is currently the most expensive (average of $491). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 6 airlines flying from Kissimmee to Florida Keys

Discover the top 6 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$54Average$171FlexibilityNo cancel feeOn-time88%
Silver AirwaysCheapest$68Average$164FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$81Average$168FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$377FlexibilityNo cancel feeOn-time71%

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