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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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Thu 12/187:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Mon 12/221:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/15$98
This Breeze Airways deal was found by Cheapflights users on 12/14. 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.
Thu 12/257:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/288:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/14$104
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/157:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/218:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/14$113
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Sun 12/287:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 1/18:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/13$117
This Breeze Airways deal was found by Cheapflights users on 12/13. 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.
Fri 12/1911:15 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/218:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/13$119
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Sun 12/287:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Mon 12/291:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/13$121
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/1911:15 amMCO - EYW
Nonstop1h 15mBreeze Airways
Fri 12/261:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/13$122
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:00 amMCO - MIA
Nonstop1h 23mAmerican Airlines
Wed 12/314:30 pmMIA - MCO
Nonstop1h 16mAmerican Airlines
Deal found 12/13$125
This Kiwi.com deal was found by Cheapflights users on 12/13. 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.
Tue 12/305:15 amMCO - MIA
1 stop7h 51mMultiple Airlines
Wed 12/318:00 amMIA - MCO
1 stop13h 25mMultiple Airlines
Deal found 12/13$133
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:25 amMCO - MIA
Nonstop1h 14mAmerican Airlines
Tue 1/69:15 amMIA - MCO
Nonstop1h 12mAmerican Airlines
Deal found 12/13$139
This Expedia deal was found by Cheapflights users on 12/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:32 pmMCO - MIA
1 stop5h 15mMultiple Airlines
Wed 1/78:00 amMIA - MCO
1 stop4h 50mMultiple Airlines
Deal found 12/13$141
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:09 amMCO - MIA
Nonstop1h 23mAmerican Airlines
Wed 1/77:05 pmMIA - MCO
Nonstop1h 22mAmerican Airlines
Deal found 12/13$142

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Kiwi.com)

One-way from

$48
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$182
Provider with most accurate pricing for Orlando (ORL)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Miami flights.
Search Deals
From Kissimmee to Florida Keys
Search Deals
One-way flight from Kissimmee to Florida Keys
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 15, 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

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 1/12

11:10 am-12:26 pm

Nonstop1h 16m

Key West

Fri 1/16

1:06 pm-2:26 pm

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 12/25

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 12/28

8:55 am-10:05 am

Nonstop1h 10m

$104

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 1/22

8:10 am-9:26 am

Nonstop1h 16m

Key West

Fri 1/23

1:06 pm-2:26 pm

Nonstop1h 20m

$104

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 12/19

11:15 am-12:30 pm

Nonstop1h 15m

Key West

Sun 12/21

8:55 am-10:05 am

Nonstop1h 10m

$119

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 12/19

11:15 am-12:30 pm

Nonstop1h 15m

Key West

Fri 12/26

1:10 pm-2:20 pm

Nonstop1h 10m

$122

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Fri 2/6

9:46 pm-11:56 am

1 stop14h 10m

Miami

Sat 2/21

7:05 am-6:00 pm

1 stop10h 55m

$124

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Wed 1/21

6:10 am-12:47 pm

1 stop6h 37m

Miami

Wed 1/21

2:57 pm-12:01 am

1 stop9h 04m

$128

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sun 1/18

5:45 am-4:40 pm

1 stop10h 55m

Miami

Fri 1/23

7:09 pm-7:31 am

1 stop12h 22m

$134

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 1/27

3:07 pm-11:56 am

2 stops20h 49m

Miami

Tue 2/3

7:00 am-6:00 pm

1 stop11h 00m

$138

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 2/26

7:50 am-9:06 am

Nonstop1h 16m

Key West

Sun 3/1

9:46 am-11:06 am

Nonstop1h 20m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 42 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, June is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $66). Flying from Kissimmee to Florida Keys in October is currently the most expensive (average of $99). 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 December 15, 2025.

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 at noon could potentially save you up to 60% 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 December 15, 2025.
Read reviews from past customers who have flown Breeze Airways, Southwest, and United 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
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
7.9
Good
4,250 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
United Airlines
7.4
Good
9,092 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,051 reviews
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Silver Airways
5.7
Fair
Breeze Airways
8.2
Very good
248 reviews

Food

6.7

Comfort

8.2

Boarding

8.4

Overall

8.2

Entertainment

6.7

Crew

8.8

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

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 $98, Breeze Airways can have you in Florida Keys from Kissimmee in 1h 16m. The distance from Kissimmee to Florida Keys is about 269 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $36. However, be on the lookout for offers from Southwest and American 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 $49. On average you can expect to pay $121. The most popular route, (Orlando - Miami), can usually be booked for $120.

  • 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, June is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $66). Flying from Kissimmee to Florida Keys in October is currently the most expensive (average of $99). 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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Alternative routes for Kissimmee to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Silver AirwaysCheapest$67Average$144FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$73Average$172FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$94Average$161FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$387FlexibilityNo cancel feeOn-time71%

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