HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$49+ Cheap flights from Kissimmee, FL to Florida Keys

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
Mar 15 — Mar 221
Sat 3/15
Sat 3/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Florida Keys 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.

Cheap flight deals from Kissimmee to Florida Keys

Keep the following information in mind while searching for Kissimmee to Florida Keys flight deals. Data was last updated March 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Delta)

One-way from

$49
(Delta)

Popular in

February

Cheapest in

August

Average price

$180
Provider with most accurate pricing for Orlando (ORL)-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Miami flights.
Search Deals
From Kissimmee to Florida Keys
Search Deals
One-way flight from Kissimmee to Florida Keys
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

Find flight deals from Kissimmee to Florida Keys

Cheapest flights from Kissimmee to Florida Keys
Explore the most affordable flight options available from Kissimmee to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2025.

This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 4/87:10 amMCO - MIA
Nonstop1h 13mDelta
Tue 4/87:55 pmMIA - MCO
Nonstop1h 20mDelta
Deal found 3/10$97
This American Airlines deal was found by Cheapflights users on 3/10. 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.
Tue 4/87:00 amMCO - MIA
Nonstop1h 16mAmerican Airlines
Tue 4/86:25 pmMIA - MCO
Nonstop1h 13mAmerican Airlines
Deal found 3/10$98
This Southwest deal was found by Cheapflights users on 3/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/317:30 amMCO - MIA
1 stop6h 35mSouthwest
Thu 4/32:55 pmMIA - MCO
1 stop6h 05mSouthwest
Deal found 3/9$117
This Mytrip deal was found by Cheapflights users on 3/10. 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.
Tue 4/17:33 amMCO - MIA
1 stop11h 00mSpirit Airlines
Wed 4/28:59 amMIA - MCO
1 stop14h 30mSpirit Airlines
Deal found 3/10$120
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/83:30 pmMCO - MIA
1 stop8h 11mFrontier
Tue 4/1510:36 amMIA - MCO
1 stop8h 57mFrontier
Deal found 3/10$150
This Mytrip deal was found by Cheapflights users on 3/9. 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 4/53:48 pmMCO - EYW
1 stop23h 41mMultiple Airlines
Tue 4/82:34 pmEYW - MCO
2 stops31h 19mMultiple Airlines
Deal found 3/9$252
This Delta deal was found by Cheapflights users on 3/8. 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.
Mon 4/76:15 amMCO - EYW
1 stop11h 00mDelta
Mon 4/147:00 amEYW - MCO
1 stop10h 15mDelta
Deal found 3/8$305
This American Airlines deal was found by Cheapflights users on 3/10. 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 6/219:09 amMCO - EYW
1 stop3h 43mAmerican Airlines
Tue 6/2411:22 amEYW - MCO
1 stop5h 23mAmerican Airlines
Deal found 3/10$391
This Mytrip deal was found by Cheapflights users on 3/9. 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 3/283:44 pmMCO - EYW
2 stops22h 41mAllegiant Air
Sun 3/308:53 amEYW - MCO
2 stops30h 01mAllegiant Air
Deal found 3/9$426
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Mon 3/247:10 pmMCO - EYW
1 stop16h 31mUnited Airlines
Fri 3/2812:45 pmEYW - MCO
1 stop22h 14mUnited Airlines
Deal found 3/9$565

Find flights from Kissimmee to Florida Keys within your budget

Customize your flight search to find flights from Kissimmee to Florida Keys 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 March 10, 2025.

Fly from

Kissimmee

Fly to

Florida Keys

Route

Depart

Return

Price

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 4/8

7:10 am-8:23 am

Nonstop1h 13m

Miami

Tue 4/8

7:55 pm-9:15 pm

Nonstop1h 20m

$97

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 4/8

7:00 am-8:16 am

Nonstop1h 16m

Miami

Tue 4/8

6:25 pm-7:38 pm

Nonstop1h 13m

$98

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Mon 3/31

7:30 am-2:05 pm

1 stop6h 35m

Miami

Thu 4/3

2:55 pm-9:00 pm

1 stop6h 05m

$117

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 4/1

7:33 am-6:33 pm

1 stop11h 00m

Miami

Wed 4/2

8:59 am-11:29 pm

1 stop14h 30m

$120

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 4/8

3:30 pm-11:41 pm

1 stop8h 11m

Miami

Tue 4/15

10:36 am-7:33 pm

1 stop8h 57m

$150

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 4/5

3:48 pm-3:29 pm

1 stop23h 41m

Key West

Tue 4/8

2:34 pm-9:53 pm

2 stops31h 19m

$252

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 4/7

6:15 am-5:15 pm

1 stop11h 00m

Key West

Mon 4/14

7:00 am-5:15 pm

1 stop10h 15m

$305

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 6/21

9:09 am-12:52 pm

1 stop3h 43m

Key West

Tue 6/24

11:22 am-4:45 pm

1 stop5h 23m

$391

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Fri 3/28

3:44 pm-2:25 pm

2 stops22h 41m

Key West

Sun 3/30

8:53 am-2:54 pm

2 stops30h 01m

$426

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Mon 3/24

7:10 pm-11:41 am

1 stop16h 31m

Key West

Fri 3/28

12:45 pm-10:59 am

1 stop22h 14m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/10

Showing 1-10 of 22 results
1
2
3

Best time to book a flight from Kissimmee to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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 Florida Keys

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

What is the cheapest month to book a flight from Kissimmee to Florida Keys?

Currently, August is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $328). Flying from Kissimmee to Florida Keys in March is currently the most expensive (average of $499). 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 EOA?

Find hourly flight availability from Kissimmee to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 10, 2025.

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

Weekly flight availability from Kissimmee to Florida Keys

Explore weekly flight availability from Kissimmee to Florida Keys. 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 March 10, 2025.

The most flights from K1S to zzEOA 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 Florida Keys by month

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

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

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

If weather is an important factor for your trip to Florida Keys, 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 68.0 F).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated March 10, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Kissimmee to Florida Keys by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,300 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
7,973 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,631 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
744 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Boarding

8.2

Food

7.1

Crew

8.7

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Kissimmee to Florida Keys one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $49. However, be on the lookout for offers from American Airlines and Spirit Airlines, as they are both options that can get you from Kissimmee to Florida Keys for a low price.

  • What are the most reliable airlines from Kissimmee to Florida Keys?

    The top 3 most reliable airlines when flying from Kissimmee to Florida Keys are Azul (48%), JetBlue (48%) and Silver Airways (48%).

  • What are the cheapest flights from Kissimmee to Florida Keys?

    The cheapest flight price from Kissimmee to Florida Keys is $86. On average you can expect to pay $139. The most popular route, (Orlando - Key West), can usually be booked for $252.

  • Can I find deals for flights from Kissimmee to Florida Keys that include hotel bookings?

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

  • How can I find direct flights from Kissimmee to Florida Keys?

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

  • Can I find deals for business class flights from Kissimmee to Florida Keys?

    Yes. Cheapflights offers flight deals from Kissimmee to Florida Keys 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 Florida Keys?

    Currently, August is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $328). Flying from Kissimmee to Florida Keys in March is currently the most expensive (average of $499). 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 Florida Keys

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

Top 5 airlines flying from Kissimmee to Florida Keys

Discover the top 5 airlines that operate flights from Kissimmee to Florida Keys. 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 March 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$45Average$119FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$86Average$177FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
Silver AirwaysCheapest$121Average$199FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$192Average$275FlexibilityNo 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.