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Key West

$54+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 82 days in advance, depart on a Friday or Monday 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 June 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/2310:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 8/2712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/5$97
This Breeze Airways deal was found by Cheapflights users on 6/4. 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.
Sun 9/138:56 am
MCO
-
EYW
Nonstop1h 23m
Breeze Airways
Thu 9/1710:59 am
EYW
-
MCO
Nonstop1h 18m
Breeze Airways
Deal found 6/4$104
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 12/78:56 am
MCO
-
EYW
Nonstop1h 23m
Breeze Airways
Fri 12/1110:59 am
EYW
-
MCO
Nonstop1h 18m
Breeze Airways
Deal found 6/5$107
This Breeze Airways deal was found by Cheapflights users on 6/4. 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.
Fri 8/710:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 8/1312:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/4$108
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 7/1910:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 7/3012:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/7$112
This Breeze Airways deal was found by Cheapflights users on 6/5. 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 6/2810:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 7/212:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/5$113
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Mon 6/810:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 6/1112:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/4$114
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 7/1010:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 7/1612:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/8$117
This Breeze Airways deal was found by Cheapflights users on 6/4. 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.
Sun 6/710:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 6/1112:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 6/4$118

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Kiwi.com)

One-way from

$54
(Kiwi.com)

Popular in

July

Cheapest in

January

Average price

$168
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. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 9, 2026.
Use the filters below to find and compare flights from Kissimmee to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 8/23

10:10 am-11:25 am

Nonstop1h 15m

Key West

Thu 8/27

12:05 pm-1:21 pm

Nonstop1h 16m

$98
Quickest round-trip

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 7/20

10:12 am-11:27 am

Nonstop1h 15m

Key West

Fri 7/24

12:07 pm-1:22 pm

Nonstop1h 15m

$113

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 6/18

10:10 am-11:25 am

Nonstop1h 15m

Key West

Fri 6/19

12:07 pm-1:22 pm

Nonstop1h 15m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 7/27

10:12 am-11:27 am

Nonstop1h 15m

Key West

Thu 7/30

12:05 pm-1:21 pm

Nonstop1h 16m

$119

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 6/19

10:12 am-11:27 am

Nonstop1h 15m

Key West

Fri 6/26

12:07 pm-1:22 pm

Nonstop1h 15m

$123

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 8/21

10:12 am-11:27 am

Nonstop1h 15m

Key West

Sun 8/23

12:05 pm-1:21 pm

Nonstop1h 16m

$128

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 7/17

10:12 am-11:27 am

Nonstop1h 15m

Key West

Sun 7/19

12:05 pm-1:21 pm

Nonstop1h 16m

$134

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 7/16

10:10 am-11:25 am

Nonstop1h 15m

Key West

Thu 7/23

12:05 pm-1:21 pm

Nonstop1h 16m

$138

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 7/16

10:10 am-11:25 am

Nonstop1h 15m

Key West

Sun 7/19

12:05 pm-1:21 pm

Nonstop1h 16m

$143
Cheapest one-way
Quickest one-way

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 6/28

10:10 am-11:25 am

Nonstop1h 15m

$58

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 19 resultsSorted by cheapest first
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

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 June 9, 2026.

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 in the morning could potentially save you up to 39% on airfare.

How much does it cost to fly round-trip from Kissimmee to Key West?

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 June 9, 2026.
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
289 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.7

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
289 reviews
Breeze Airways
8.2
Very good
289 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.7

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
7.1
Good
11,643 reviews
Breeze Airways
8.2
Very good
289 reviews

Overall

8.2

Food

6.7

Boarding

8.3

Crew

8.7

Comfort

8.2

Entertainment

6.7

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

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 4 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 $49. On average you can expect to pay $108. 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.

See more FAQs

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Top 4 airlines flying from Kissimmee to Key West

Discover the top 4 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$43Average$126FlexibilityNo cancel feeOn-time69%
Allegiant AirCheapest$65Average$113FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$84Average$153FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$443FlexibilityNo cancel feeOn-time71%

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