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Key West

$48+ Cheap flights from Kissimmee, FL to Key West (EYW)

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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Jan 4 — Jan 111
Sun 1/4
Sun 1/11
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in August or September, booked 67 days in advance, depart on a Monday or Thursday and return on a Monday

Cheap flight deals from Kissimmee to Key West

Cheapest flights from Kissimmee to Key West
Explore the most affordable flight options available from Kissimmee to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/4. 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
Sun 12/218:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/4$97
This Breeze Airways deal was found by Cheapflights users on 12/4. 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 12/117:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 12/188:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/4$98
This CheapOair deal was found by Cheapflights users on 12/4. 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 CheapOair 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 12/4$102
This Breeze Airways deal was found by Cheapflights users on 12/3. 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 12/127:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/148:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/3$108
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/257:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Mon 12/291:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/4$109
This Breeze Airways deal was found by Cheapflights users on 12/3. 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 12/287:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 1/18:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/3$113
This CheapOair deal was found by Cheapflights users on 12/3. 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 CheapOair 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
Fri 1/21:10 pmEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/3$117
This Breeze Airways deal was found by Cheapflights users on 12/4. 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 12/117:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/148:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/4$118
This Expedia deal was found by Cheapflights users on 12/3. 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.
Sun 12/287:00 amMCO - EYW
Nonstop1h 15mMultiple Airlines
Thu 1/112:20 pmEYW - MCO
1 stop5h 09mMultiple Airlines
Deal found 12/3$123
This Expedia deal was found by Cheapflights users on 12/4. 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.
Thu 12/187:00 amMCO - EYW
Nonstop1h 15mMultiple Airlines
Sun 12/2112:20 pmEYW - MCO
1 stop5h 09mMultiple Airlines
Deal found 12/4$139
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/57:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Mon 12/88:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 12/3$143
This Cheapflightsfares deal was found by Cheapflights users on 12/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amMCO - EYW
1 stop4h 35mSpirit Airlines
Tue 12/3012:20 pmEYW - MCO
1 stop5h 09mSpirit Airlines
Deal found 12/3$144

Find flight deals from Kissimmee to Key West

Keep the following information in mind while searching for Kissimmee to Key West flight deals. Data was last updated December 5, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$97
(Kiwi.com)

One-way from

$48
(Kiwi.com)

Popular in

July

Cheapest in

August

Average price

$173
Provider with most accurate pricing for Orlando (ORL)-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Key West flights.
Search Deals
From Kissimmee to Key West
Search Deals
One-way flight from Kissimmee to Key West
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 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 Key West 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 5, 2025.
Use the filters below to find and compare flights from Kissimmee to Key West that are best for you.

Fly from

Kissimmee

Fly to

Key West

Route

Depart

Return

Price

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 12/18

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 12/21

8:55 am-10:05 am

Nonstop1h 10m

$97

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 1/4

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 1/11

10:06 am-11:26 am

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 1/22

8:10 am-9:26 am

Nonstop1h 16m

Key West

Sun 1/25

10:06 am-11:26 am

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 1/18

8:10 am-9:26 am

Nonstop1h 16m

Key West

Thu 1/22

10:06 am-11:26 am

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 2/8

7:50 am-9:06 am

Nonstop1h 16m

Key West

Sun 2/15

9:46 am-11:06 am

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 2/5

7:50 am-9:06 am

Nonstop1h 16m

Key West

Sun 2/8

9:46 am-11:06 am

Nonstop1h 20m

$104

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 1/23

11:10 am-12:26 pm

Nonstop1h 16m

Key West

Sun 1/25

10:06 am-11:26 am

Nonstop1h 20m

$108

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 12/28

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 1/1

8:55 am-10:05 am

Nonstop1h 10m

$113

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 2/12

7:50 am-9:06 am

Nonstop1h 16m

Key West

Sun 2/15

9:46 am-11:06 am

Nonstop1h 20m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 3/1

7:50 am-9:06 am

Nonstop1h 16m

Key West

Thu 3/5

9:46 am-11:06 am

Nonstop1h 20m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 22 results
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Best time to book a flight from Kissimmee to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West 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 Key West

How far ahead should I book a flight from Kissimmee to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Kissimmee to Key West. Price data was last updated on November 28, 2025.

The best time to book flights from Kissimmee to Key West is 67 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Kissimmee to Key West?

Currently, June is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $66). Flying from Kissimmee to Key West 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 EYW?

Find hourly flight availability from Kissimmee to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 5, 2025.

One of the essential ways to save on airfare from Kissimmee to Key West 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 Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated December 5, 2025.
Read through reviews of airlines operating flights from Kissimmee to Key West, such as Breeze Airways, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
242 reviews
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
United Airlines
7.4
Good
9,065 reviews
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
American Airlines
7.2
Good
11,046 reviews
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
JetBlue
7.2
Good
2,897 reviews
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Silver Airways
5.7
Fair
237 reviews
Breeze Airways
8.2
Very good
242 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.2

Overall

8.2

Crew

8.8

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Key West from Kissimmee?

    If you book a flight to Key West from Kissimmee, you will be flying to Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West. There are 0 flights from Kissimmee to Key West per day from 6 different airlines.

  • How long is the flight from Kissimmee to Key West?

    Airlines like Breeze Airways fly from Kissimmee to Key West in about 1h 15m. The time it takes to get you to your destination is usually consistent. The distance from Kissimmee to Key West is about 269 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Kissimmee to Key West one-way?

    The cheapest airlines for a one-way flight from Kissimmee to Key West are Breeze Airways ($58), United Airlines ($64), and Silver Airways ($83).

  • What are the cheapest flights from Kissimmee to Key West?

    The cheapest flight price from Kissimmee to Key West is $59. On average you can expect to pay $116. The most popular route, (Orlando - Key West), can usually be booked for $98.

  • Can I find deals for flights from Kissimmee to Key West that include hotel bookings?

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

  • How can I find direct flights from Kissimmee to Key West?

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

  • Can I find deals for business class flights from Kissimmee to Key West?

    Yes. Cheapflights offers flight deals from Kissimmee to Key West 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 Key West?

    Currently, June is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $66). Flying from Kissimmee to Key West 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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Top 6 airlines flying from Kissimmee to Key West

Discover the top 6 airlines that operate flights from Kissimmee to Key West. 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 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Silver AirwaysCheapest$67Average$149FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$73Average$172FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Breeze AirwaysCheapest$93Average$163FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$192Average$386FlexibilityNo cancel feeOn-time71%

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