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Key West

$93+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in January or February, booked 72 days in advance, depart on a Thursday or Sunday and return on a Sunday

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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$118
(Priceline)

One-way from

$93
(Priceline)

Popular in

April

Cheapest in

January

Average price

$224
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. 10% potential increase in price ($22 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 May 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 May 1, 2025.

This Priceline deal was found by Cheapflights users on 4/30. 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 6/1512:02 pmMCO - EYW
Nonstop1h 15mBreeze Airways
Thu 6/2610:12 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 4/30$118
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/249:27 pmMCO - EYW
1 stop19h 18mMultiple Airlines
Tue 5/274:16 pmEYW - MCO
2 stops28h 21mMultiple Airlines
Deal found 4/30$258
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/44:13 pmMCO - EYW
1 stop23h 14mAllegiant Air
Sun 6/84:17 pmEYW - MCO
1 stop23h 20mAllegiant Air
Deal found 4/30$267
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2411:47 amMCO - EYW
1 stop5h 05mAmerican Airlines
Tue 5/2711:28 amEYW - MCO
1 stop5h 10mAmerican Airlines
Deal found 4/30$389
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1211:10 amMCO - EYW
2 stops23h 49mDelta
Fri 9/197:00 amEYW - MCO
2 stops12h 41mDelta
Deal found 4/29$546
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/128:05 amMCO - EYW
2 stops23h 55mUnited Airlines
Mon 6/166:45 pmEYW - MCO
2 stops23h 14mUnited Airlines
Deal found 4/30$550

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 May 1, 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

Sun 6/15

12:02 pm-1:17 pm

Nonstop1h 15m

Key West

Thu 6/26

10:12 am-11:22 am

Nonstop1h 10m

$118

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 5/24

9:27 pm-4:45 pm

1 stop19h 18m

Key West

Tue 5/27

4:16 pm-8:37 pm

2 stops28h 21m

$258

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Wed 6/4

4:13 pm-3:27 pm

1 stop23h 14m

Key West

Sun 6/8

4:17 pm-3:37 pm

1 stop23h 20m

$267

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 5/24

11:47 am-4:52 pm

1 stop5h 05m

Key West

Tue 5/27

11:28 am-4:38 pm

1 stop5h 10m

$389

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 6/12

8:05 am-8:00 am

2 stops23h 55m

Key West

Mon 6/16

6:45 pm-5:59 pm

2 stops23h 14m

$550

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 5/16

12:00 pm-5:30 pm

1 stop5h 30m

Key West

Sun 5/18

6:25 pm-12:24 am

1 stop5h 59m

$1,263

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 7/10

11:52 am-1:07 pm

Nonstop1h 15m

$93

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Wed 6/25

4:13 pm-3:27 pm

1 stop23h 14m

$114

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 6/1

9:51 am-4:57 pm

1 stop7h 06m

$115

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 5/30

9:59 am-12:51 pm

1 stop2h 52m

$195

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 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 April 25, 2025.

The best time to book flights from Kissimmee to Key West is 72 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, August is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $328). Flying from Kissimmee to Key West in March is currently the most expensive (average of $492). 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 May 1, 2025.

When flying from Kissimmee to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Kissimmee to Key West?

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Key West. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kissimmee to Key West flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 May 1, 2025.
To help decide which airline to fly from Kissimmee to Key West, see what other customers have to say about Breeze Airways, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
734 reviews
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
160 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 ($93), Allegiant Air ($114), and American Airlines ($195).

  • What are the most reliable airlines from Kissimmee to Key West?

    No one likes to see their flight delayed. When booking a flight from Kissimmee to Key West consider choosing Azul (39%), JetBlue (39%) or Avianca (39%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Kissimmee to Key West is $40. On average you can expect to pay $91. The most popular route, (Orlando - Key West), can usually be booked for $102.

  • 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, August is the cheapest month in which you can book a flight from Kissimmee to Key West (average of $328). Flying from Kissimmee to Key West in March is currently the most expensive (average of $492). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$45Average$106FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$81Average$104FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Silver AirwaysCheapest$89Average$185FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$192Average$280FlexibilityNo cancel feeOn-time71%

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