HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Kissimmee to Key West are usually found in September or December, booked 62 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 April 27, 2026.

This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 5/2812:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/24$88
This Mytrip deal was found by Cheapflights users on 4/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3110:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Fri 6/512:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Deal found 4/25$89
This Mytrip deal was found by Cheapflights users on 4/24. 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 Mytrip 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 6/1812:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/24$92
This Mytrip deal was found by Cheapflights users on 4/23. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1710:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 5/2112:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/23$95
This Mytrip deal was found by Cheapflights users on 4/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:12 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Thu 5/2112:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/26$96
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/37:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 5/712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/22$97
This Mytrip deal was found by Cheapflights users on 4/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:10 am
MCO
-
EYW
Nonstop1h 15m
Breeze Airways
Fri 5/2912:07 pm
EYW
-
MCO
Nonstop1h 15m
Breeze Airways
Deal found 4/25$99
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:55 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 4/309:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 4/22$100
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Mon 5/411:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
Thu 5/712:05 pm
EYW
-
MCO
Nonstop1h 16m
Breeze Airways
Deal found 4/26$101

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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$88
(Mytrip)

One-way from

$44
(Booking.com)

Popular in

July

Cheapest in

September

Average price

$208
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. 11% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 27, 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
Quickest round-trip

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 5/28

10:10 am-11:25 am

Nonstop1h 15m

Key West

Sun 5/31

12:05 pm-1:21 pm

Nonstop1h 16m

$198

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 5/1

11:10 am-12:26 pm

Nonstop1h 16m

Key West

Sun 5/3

9:46 am-11:06 am

Nonstop1h 20m

$278

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 5/8

6:25 pm-1:45 pm

1 stop19h 20m

Key West

Fri 5/15

4:47 pm-5:48 pm

1 stop25h 01m

$719

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 5/9

5:10 pm-3:07 pm

2 stops21h 57m

Key West

Wed 5/13

2:49 pm-3:12 pm

2 stops24h 23m

$729

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Tue 5/12

4:21 pm-1:45 pm

2 stops21h 24m

Key West

Tue 5/19

2:49 pm-11:20 am

2 stops20h 31m

$775

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 5/29

11:35 am-1:30 pm

2 stops25h 55m

Key West

Tue 6/2

2:26 pm-9:45 am

2 stops19h 19m

$797

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 5/24

6:10 pm-3:07 pm

1 stop20h 57m

Key West

Thu 5/28

2:26 pm-5:03 pm

1 stop26h 37m

$834

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 5/10

6:40 am-1:45 pm

1 stop7h 05m

Key West

Thu 5/14

2:49 pm-10:20 pm

1 stop7h 31m

$880
Cheapest one-way
Quickest one-way

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 5/7

10:10 am-11:25 am

Nonstop1h 15m

$64

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Wed 5/20

10:10 am-11:10 am

1 stop25h 00m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 17 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 April 27, 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 37% 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 April 27, 2026.
Read through reviews of airlines operating flights from Kissimmee to Key West, such as Breeze Airways,Allegiant Air, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
281 reviews

Overall

8.1

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Food

6.6

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
8.1
Very good
281 reviews
Breeze Airways
8.1
Very good
281 reviews

Overall

8.1

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Food

6.6

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.
Allegiant Air
7.3
Good
706 reviews
Breeze Airways
8.1
Very good
281 reviews

Overall

8.1

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Food

6.6

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
11,673 reviews
Breeze Airways
8.1
Very good
281 reviews

Overall

8.1

Entertainment

6.6

Crew

8.7

Boarding

8.3

Comfort

8.2

Food

6.6

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 5 different airlines.

  • How long is the flight from Kissimmee to Key West?

    Airlines like Breeze Airways and United Airlines fly from Kissimmee to Key West in about 1h 15m. The time it takes to get you to your destination can typically vary by up to 18h 05m. The distance from Kissimmee to Key West is about 269 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest flight price from Kissimmee to Key West is $51. On average you can expect to pay $110. The most popular route, (Orlando - Key West), can usually be booked for $93.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kissimmee to Key West

See prices for flight routes from nearby airports that may be better suited for you.
Tampa to Fort Lauderdale flights
Orlando to Miami flights
Tampa to Miami flights
Miami to Orlando flights
Fort Lauderdale to Tampa flights
Jacksonville to Miami flights
Pensacola to Miami flights
Fort Lauderdale to Orlando flights
Miami to Tampa flights
Orlando to Fort Lauderdale flights
Orlando to Key West flights
Tampa to Key West flights
Orlando to Pensacola flights
Fort Lauderdale to Jacksonville flights
Miami to Jacksonville flights
Pensacola to Orlando flights
Fort Lauderdale to Pensacola flights
Miami to Pensacola flights
Jacksonville to Fort Lauderdale flights
Pensacola to Fort Lauderdale flights
Valparaiso to Orlando flights
Miami to Tallahassee flights
Pensacola to Key West flights
Tallahassee to Miami flights
Tallahassee to Fort Lauderdale flights
Fort Lauderdale to Tallahassee flights
West Palm Beach to Jacksonville flights
Tampa to Orlando flights
Fort Myers to Orlando flights
Miami to Valparaiso flights
Tampa to Pensacola flights
Sarasota to Miami flights
Panama City to Fort Lauderdale flights
Pensacola to Tampa flights
Panama City to Miami flights
Jacksonville to Key West flights
West Palm Beach to Pensacola flights
Fort Lauderdale to Key West flights
Orlando to Panama City flights
Pensacola to West Palm Beach flights
Miami to Panama City flights
Fort Lauderdale to Panama City flights
Tampa to Panama City flights
Orlando to Tampa flights
Tampa to Jacksonville flights
Valparaiso to Miami flights
West Palm Beach to Key West flights
Jacksonville to Orlando flights
West Palm Beach to Tampa flights

Top 5 airlines flying from Kissimmee to Key West

Discover the top 5 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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$43Average$87FlexibilityNo cancel feeOn-time69%
Silver AirwaysCheapest$66Average$76FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$73Average$111FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$87Average$156FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$440FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights