HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$86+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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.

The best prices from Kissimmee to Key West are usually found in January or February, booked 72 days in advance, depart on a Sunday or Thursday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$169
(Trip.com)

One-way from

$86
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$173
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. 10% 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 February 2025
Search Deals

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 February 20, 2025.

This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/58:45 amMCO - EYW
Nonstop1h 25mSilver Airways
Sat 4/127:40 pmEYW - MCO
Nonstop1h 25mSilver Airways
Deal found 2/19$169
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/78:45 amMCO - EYW
Nonstop1h 25mUnited Airlines
Sun 3/97:40 pmEYW - MCO
Nonstop1h 25mUnited Airlines
Deal found 2/19$173
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/191:33 pmMCO - EYW
1 stop5h 16mAmerican Airlines
Wed 3/267:29 pmEYW - MCO
1 stop4h 39mAmerican Airlines
Deal found 2/19$193
This JetBlue 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1512:55 pmMCO - EYW
Nonstop1h 25mJetBlue
Sat 5/173:05 pmEYW - MCO
Nonstop1h 25mJetBlue
Deal found 2/20$239
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/177:00 amMCO - EYW
1 stop9h 18mMultiple Airlines
Thu 3/208:53 amEYW - MCO
3 stops16h 15mMultiple Airlines
Deal found 2/19$297
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/284:29 pmMCO - EYW
2 stops22h 34mAllegiant Air
Sun 3/28:53 amEYW - MCO
2 stops30h 46mAllegiant Air
Deal found 2/19$370

Find flights from Kissimmee to Key West within your budget

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 February 20, 2025.

Fly from

Kissimmee

Fly to

Key West

Route

Depart

Return

Price

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 4/5

8:45 am-10:10 am

Nonstop1h 25m

Key West

Sat 4/12

7:40 pm-9:05 pm

Nonstop1h 25m

$169

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 3/7

8:45 am-10:10 am

Nonstop1h 25m

Key West

Sun 3/9

7:40 pm-9:05 pm

Nonstop1h 25m

$173

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Wed 3/19

1:33 pm-6:49 pm

1 stop5h 16m

Key West

Wed 3/26

7:29 pm-12:08 am

1 stop4h 39m

$193

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Thu 5/15

12:55 pm-2:20 pm

Nonstop1h 25m

Key West

Sat 5/17

3:05 pm-4:30 pm

Nonstop1h 25m

$239

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 3/17

7:00 am-4:18 pm

1 stop9h 18m

Key West

Thu 3/20

8:53 am-1:08 am

3 stops16h 15m

$297

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 4/5

3:48 pm-3:29 pm

1 stop23h 41m

Key West

Sat 4/12

3:04 pm-4:30 pm

2 stops25h 26m

$304

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 3/7

8:45 am-10:10 am

Nonstop1h 25m

$86

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 4/14

12:55 pm-2:20 pm

Nonstop1h 25m

$87

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Wed 3/19

11:16 am-5:25 pm

1 stop6h 09m

$97

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 3/1

8:10 pm-4:37 pm

1 stop20h 27m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 13 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.

Travel insights for flights from Kissimmee to Key West

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

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 February 14, 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 $510). 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 February 20, 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.

Weekly flight availability from Kissimmee to Key West

Explore weekly flight availability from Kissimmee to Key West. 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 K1S to EYW 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 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 February 20, 2025.
To help decide which airline to fly from Kissimmee to Key West, see what other customers have to say about JetBlue, United Airlines and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

JetBlue
7.4
Good
3,070 reviews
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

United Airlines
7.4
Good
8,766 reviews
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

Allegiant Air
7.3
Good
765 reviews
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

American Airlines
7.2
Good
10,000 reviews
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

Silver Airways
6.0
Okay
259 reviews
JetBlue
7.4
Good
3,070 reviews

Entertainment

7.3

Crew

8.1

Food

6.8

Comfort

7.7

Boarding

7.6

Overall

7.4

Reviews

1 / 20

4.0
Okay

Charles,Aug 2024

MCO - BDL

we were told the night before that the flight would be delayed ~50 minutes but that we should show up on time. We did but at the new doors open time people were still deplaning from our aircraft. We finally left the gate 1:48 minutes late but the captain said an indicator showed and we weren't allowed to taxi. Maintenace came on board did some stuff, then we took off. Because of Tropical storm Debbie we went way east over the ocean. It was still rough though no fault of Jet Blue.

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 12 flights from Kissimmee to Key West per day from 5 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 Silver Airways ($86), United Airlines ($87), and American Airlines ($97).

  • 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 (46%), JetBlue (46%) or Silver Airways (46%) 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 $83. On average you can expect to pay $139. The most popular route, (Orlando - Key West), can usually be booked for $166.

  • 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 $510). 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

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.
Miami to Orlando flights
Orlando to Miami flights
Tampa to Fort Lauderdale flights
Tampa to Miami flights
Fort Lauderdale to Orlando flights
Pensacola to Fort Lauderdale flights
Fort Lauderdale to Tampa flights
Miami to Tampa flights
Jacksonville to Miami flights
Fort Lauderdale to Pensacola flights
Pensacola to Orlando flights
Orlando to Key West flights
Fort Lauderdale to Tallahassee flights
Fort Lauderdale to Jacksonville flights
Tampa to Key West flights
Pensacola to Miami flights
Orlando to Fort Lauderdale flights
Tallahassee to Fort Lauderdale flights
Jacksonville to Fort Lauderdale flights
Miami to Jacksonville flights
Tampa to Pensacola flights
Pensacola to Tampa flights
Tallahassee to Miami flights
Miami to Tallahassee flights
Orlando to Pensacola flights
Miami to Pensacola flights
Jacksonville to Key West flights
Tallahassee to West Palm Beach flights
Fort Lauderdale to Key West flights
Sarasota to Key West flights
West Palm Beach to Pensacola flights
Fort Myers to Pensacola flights
West Palm Beach to Tallahassee flights
Tampa to Panama City flights
Miami to Key West flights
Tampa to West Palm Beach flights
Fort Myers to Orlando flights
Tampa to Tallahassee flights
Miami to Panama City flights
Orlando to Jacksonville flights
West Palm Beach to Tampa flights
Fort Myers to Key West flights
Orlando to Tampa flights
Jacksonville to West Palm Beach flights
Miami to Gainesville flights
Valparaiso to Miami flights
Tampa to Jacksonville flights
Tampa to Orlando flights
Pensacola to Key West flights
Gainesville to Miami 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$45Average$121FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$119Average$265FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$121Average$203FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$192Average$269FlexibilityNo 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.