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Kissimmee

$86+ Cheap flights from Key West (EYW) to Kissimmee, FL

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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MCO
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Key West to Kissimmee

Keep the following information in mind while searching for Key West to Kissimmee flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(Expedia)

One-way from

$86
(Cheapflightsfares)

Popular in

April

Cheapest in

February

Average price

$158
Provider with most accurate pricing for Key West-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Key West-Orlando (ORL) flights.
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From Key West to Kissimmee
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One-way flight from Key West to Kissimmee
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Highest demand for flights based on searches. 19% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Key West to Kissimmee

Cheapest flights from Key West to Kissimmee
Explore the most affordable flight options available from Key West to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Expedia deal was found by Cheapflights users on 2/19. 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 4/103:05 pmEYW - MCO
Nonstop1h 25mSilver Airways
Sun 4/138:45 amMCO - EYW
Nonstop1h 25mSilver Airways
Deal found 2/19$166
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/147:40 pmEYW - MCO
Nonstop1h 25mUnited Airlines
Tue 3/188:45 amMCO - EYW
Nonstop1h 25mUnited Airlines
Deal found 2/20$174
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 3/67:29 pmEYW - MCO
1 stop4h 40mAmerican Airlines
Sat 5/1011:36 amMCO - EYW
1 stop5h 16mAmerican Airlines
Deal found 2/20$193
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Thu 3/64:23 pmEYW - MCO
2 stops31h 36mMultiple Airlines
Sat 5/108:24 pmMCO - EYW
2 stops19h 10mMultiple Airlines
Deal found 2/20$291
This JetBlue Airways deal was found by Cheapflights users on 2/20. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/237:40 pmEYW - MCO
Nonstop1h 25mJetBlue
Wed 2/268:45 amMCO - EYW
Nonstop1h 25mJetBlue
Deal found 2/20$322
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 3/75:08 pmEYW - MCO
2 stops21h 52mAllegiant Air
Tue 3/1111:05 amMCO - EYW
2 stops27h 11mAllegiant Air
Deal found 2/20$331
This Delta deal was found by Cheapflights users on 2/20. 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 3/142:45 pmEYW - MCO
1 stop4h 58mDelta
Wed 3/194:10 pmMCO - EYW
1 stop4h 20mDelta
Deal found 2/20$1,412

Find flights from Key West to Kissimmee within your budget

Customize your flight search to find flights from Key West to Kissimmee 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 February 20, 2025.

Fly from

Key West

Fly to

Kissimmee

Route

Depart

Return

Price

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 4/10

3:05 pm-4:30 pm

Nonstop1h 25m

Orlando

Sun 4/13

8:45 am-10:10 am

Nonstop1h 25m

$166

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 3/14

7:40 pm-9:05 pm

Nonstop1h 25m

Orlando

Tue 3/18

8:45 am-10:10 am

Nonstop1h 25m

$174

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 3/6

7:29 pm-12:09 am

1 stop4h 40m

Orlando

Fri 3/7

11:16 am-5:33 pm

1 stop6h 17m

$193

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 3/6

4:23 pm-11:59 pm

2 stops31h 36m

Orlando

Sat 5/10

8:24 pm-3:34 pm

2 stops19h 10m

$291

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 3/7

5:08 pm-3:00 pm

2 stops21h 52m

Orlando

Tue 3/11

11:05 am-2:16 pm

2 stops27h 11m

$331

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 4/10

1:06 pm-8:51 pm

1 stop7h 45m

Orlando

Sun 4/13

12:55 pm-2:20 pm

Nonstop1h 25m

$510

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Fri 3/14

2:45 pm-7:43 pm

1 stop4h 58m

Orlando

Wed 3/19

4:10 pm-8:30 pm

1 stop4h 20m

$1,412

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Sun 3/9

7:40 pm-9:05 pm

Nonstop1h 25m

$86

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Thu 3/13

7:40 pm-9:05 pm

Nonstop1h 25m

$87

Key WestOrlando

EYW - MCO

EYWMCO

Key West

Mon 3/10

7:29 pm-12:08 am

1 stop4h 39m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 12 results
1
2

Best time to book a flight from Key West to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Key West 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.

Travel insights for flights from Key West to Kissimmee

Get recent, data-driven insights about flights from Key West to Kissimmee including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Key West to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $206). Flying from Key West to Kissimmee in November is currently the most expensive (average of $289). 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 EYW to K1S?

Find hourly flight availability from Key West to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Key West to Kissimmee, 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 Key West to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Key West to Kissimmee. Price data was last updated on February 16, 2025.

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

Weekly flight availability from Key West to Kissimmee

Explore weekly flight availability from Key West to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 20, 2025.

The most flights from EYW to K1S are scheduled on a Monday (12 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (12 on average).

Rainfall in Kissimmee by month

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

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

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

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July 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 60.8 F).

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated February 20, 2025.
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

JetBlue
7.4
Good
3,070 reviews
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Allegiant Air
7.3
Good
765 reviews
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,220 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

8.0

Reviews

1 / 20

2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Key West to Kissimmee. 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 from for flights from Key West to Kissimmee?

    Key West (EYW), located 2.6 mi from the city center, is the airport you fly out of when you book flights from Key West to Kissimmee. 3 airlines have flights from Key West to Kissimmee on a regular basis. Booking flights from Key West to Kissimmee should not be difficult; the airport handles an average of 12 outbound flights to Kissimmee per day.

  • What are the cheapest airlines to fly from Key West to Kissimmee one-way?

    For one-way options, check prices for Silver Airways. According to our data, you can fly for as low as $86. Users have also found prices from $87 and $97 on United Airlines and American Airlines, respectively.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Key West to Kissimmee on time: Azul (43%), JetBlue (43%), Silver Airways (43%).

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

    Looking for the cheapest flight from Key West to Kissimmee? While on average our users pay $157, our data indicates the cheapest price to be $86. The most popular route (Key West - Orlando), is priced around $166.

  • Can I find deals for flights from Key West to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Key West to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Kissimmee.

  • Can I find deals for business class flights from Key West to Kissimmee?

    Yes. Cheapflights offers flight deals from Key West to Kissimmee 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 Key West to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Key West to Kissimmee (average of $206). Flying from Key West to Kissimmee in November is currently the most expensive (average of $289). 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.

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Top 3 airlines flying from Key West to Kissimmee

Discover the top 3 airlines that operate flights from Key West to Kissimmee. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$68Average$102FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
Silver AirwaysCheapest$118Average$226FlexibilityNo cancel feeOn-timeN/A
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