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Key West

$44+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in November or August, booked 36 days in advance, depart on a Monday or Sunday and return on a Wednesday

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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 2/227:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 2/269:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/26$96
This Breeze Airways deal was found by Cheapflights users on 1/25. 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 3/17:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 3/59:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/25$98
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 4/27:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Sun 4/59:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/24$102
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/57:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 2/129:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/25$103
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 3/57:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Sun 3/89:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/25$104
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 2/18:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Mon 2/21:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/23$106
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 2/2311:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Mon 3/21:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/24$107
This Breeze Airways deal was found by Cheapflights users on 1/26. 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 2/57:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Sun 2/89:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/26$108
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/127:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 3/269:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/24$111

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 January 26, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$96
(Kiwi.com)

One-way from

$44
(Mytrip)

Popular in

July

Cheapest in

November

Average price

$188
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. 5% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 26, 2026.
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

Sun 3/1

7:50 am-9:06 am

Nonstop1h 16m

Key West

Thu 3/5

9:46 am-11:06 am

Nonstop1h 20m

$98

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 2/23

11:10 am-12:26 pm

Nonstop1h 16m

Key West

Mon 3/2

1:06 pm-2:26 pm

Nonstop1h 20m

$104

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 3/12

7:50 am-9:06 am

Nonstop1h 16m

Key West

Thu 3/19

9:46 am-11:06 am

Nonstop1h 20m

$104

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 2/1

8:10 am-9:26 am

Nonstop1h 16m

Key West

Sun 2/8

9:46 am-11:06 am

Nonstop1h 20m

$108

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 2/5

7:50 am-9:06 am

Nonstop1h 16m

Key West

Fri 2/6

1:06 pm-2:26 pm

Nonstop1h 20m

$108

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 2/12

7:50 am-9:06 am

Nonstop1h 16m

Key West

Thu 2/19

9:46 am-11:06 am

Nonstop1h 20m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 3/29

7:50 am-9:06 am

Nonstop1h 16m

Key West

Thu 4/2

9:46 am-11:06 am

Nonstop1h 20m

$128

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 4/2

7:50 am-9:06 am

Nonstop1h 16m

Key West

Mon 4/6

1:06 pm-2:26 pm

Nonstop1h 20m

$134

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 1/29

8:10 am-9:26 am

Nonstop1h 16m

Key West

Sun 2/1

10:06 am-11:26 am

Nonstop1h 20m

$158

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 4/26

6:00 am-11:17 am

1 stop5h 17m

Key West

Thu 4/30

9:46 am-11:06 am

Nonstop1h 20m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January 23, 2026.

The best time to book flights from Kissimmee to Key West is 36 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 January 26, 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 41% 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 January 26, 2026.
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
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,205 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,197 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
JetBlue
7.2
Good
2,890 reviews
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Silver Airways
5.7
Fair
Breeze Airways
8.2
Very good
263 reviews

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Comfort

8.2

Crew

8.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 16m. 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 ($49), Silver Airways ($83), and United Airlines ($86).

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

    The cheapest flight price from Kissimmee to Key West is $44. On average you can expect to pay $89. The most popular route, (Orlando - Key West), can usually be booked for $96.

  • 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$43Average$161FlexibilityNo cancel feeOn-time69%
Allegiant AirCheapest$58Average$200FlexibilityNo cancel feeOn-time88%
Silver AirwaysCheapest$66Average$133FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$90Average$157FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$387FlexibilityNo cancel feeOn-time71%

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