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Key West

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

MCO — EYW
Oct 23 — Oct 301
Fri 10/23
Fri 10/30
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in January or August, booked 83 days in advance, depart on a Friday or Monday and return on a Monday

Find flight deals from Kissimmee to Key West

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

October

Cheapest in

January

Average price

$184
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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Highest demand for flights based on searches. 8% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Insights

Everything you need to know about your flight from Kissimmee to Key West

What is the cheapest time of day to fly from K1S to EYW?

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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% on airfare.

Reviews of airlines servicing Key West

Read through reviews of airlines operating flights from Kissimmee to Key West, such as Breeze Airways 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
326 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Food

6.8

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
326 reviews
Breeze Airways
8.2
Very good
326 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Food

6.8

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.0
Good
12,075 reviews
Breeze Airways
8.2
Very good
326 reviews

Boarding

8.4

Entertainment

6.7

Crew

8.8

Overall

8.2

Food

6.8

Comfort

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

  • 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 3 different airlines.

  • 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 Allegiant Air ($27), Breeze Airways ($49), and American Airlines ($240).

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

    The cheapest flight price from Kissimmee to Key West is $49. On average you can expect to pay $114. The most popular route, (Orlando - Key West), can usually be booked for $97.

  • 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.

See more FAQs

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Top 3 airlines flying from Kissimmee to Key West

AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$78Average$114FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$81Average$154FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$295Average$491FlexibilityNo cancel feeOn-time71%

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