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Key West

$59+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 Tuesday and return on a Monday

Cheap 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 October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(Breeze Airways)

One-way from

$59
(Breeze Airways)

Popular in

July

Cheapest in

August

Average price

$173
Provider with most accurate pricing for Orlando (ORL)-Key West flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Key West flights.
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From Kissimmee to Key West
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One-way flight from Kissimmee to Key West
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Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 16, 2025.

This Breeze Airways deal was found by Cheapflights users on 10/16. 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 11/67:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 11/138:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/16$118
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 11/68:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/16$122
This Breeze Airways deal was found by Cheapflights users on 10/16. 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 12/47:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Fri 12/58:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/16$124
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Sun 11/97:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Fri 11/148:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/14$126
This Expedia deal was found by Cheapflights users on 10/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 11/98:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/15$128
This Breeze Airways deal was found by Cheapflights users on 10/15. 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.
Thu 12/47:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Sun 12/78:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/15$130
This Breeze Airways deal was found by Cheapflights users on 10/14. 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.
Mon 10/207:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Fri 10/248:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/14$134
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:00 amMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 10/308:55 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 10/16$136
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline 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 10/14$142

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 October 16, 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 11/6

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 11/13

8:55 am-10:05 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 11/3

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 11/6

8:55 am-10:05 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 11/9

7:00 am-8:15 am

Nonstop1h 15m

Key West

Fri 11/14

8:55 am-10:05 am

Nonstop1h 10m

$126

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

$134

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 10/31

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 11/2

8:55 am-10:05 am

Nonstop1h 10m

$134

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 10/26

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 10/30

8:55 am-10:05 am

Nonstop1h 10m

$136

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 11/28

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 11/30

8:55 am-10:05 am

Nonstop1h 10m

$138

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 11/27

7:00 am-8:15 am

Nonstop1h 15m

Key West

Sun 11/30

8:55 am-10:05 am

Nonstop1h 10m

$138

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

$144

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 10/27

7:00 am-8:15 am

Nonstop1h 15m

Key West

Thu 10/30

8:55 am-10:05 am

Nonstop1h 10m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 20 results
1
2

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 October 10, 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 April is currently the most expensive (average of $90). 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 October 16, 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 October 16, 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
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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
8.1
Very good
217 reviews
Breeze Airways
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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
8,982 reviews
Breeze Airways
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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
11,040 reviews
Breeze Airways
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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
2,907 reviews
Breeze Airways
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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
240 reviews
Breeze Airways
8.1
Very good
217 reviews

Entertainment

6.6

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Overall

8.1

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 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 flights from Kissimmee to Key West?

    The cheapest flight price from Kissimmee to Key West is $59. On average you can expect to pay $119. The most popular route, (Orlando - Key West), can usually be booked for $118.

  • 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 April is currently the most expensive (average of $90). 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Silver AirwaysCheapest$67Average$160FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$75Average$171FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$85Average$169FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$192Average$385FlexibilityNo cancel feeOn-time71%

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