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Florida Keys

$67+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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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 April 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$109
(Kiwi.com)

One-way from

$67
(Delta)

Popular in

December

Cheapest in

August

Average price

$177
Provider with most accurate pricing for Orlando (ORL)-Miami flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Miami flights.
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From Kissimmee to Florida Keys
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One-way flight from Kissimmee to Florida Keys
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Highest demand for flights based on searches. 17% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 30, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2212:02 pmMCO - EYW
Nonstop1h 15mBreeze Airways
Fri 6/2710:12 amEYW - MCO
Nonstop1h 10mBreeze Airways
Deal found 4/29$109
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/77:55 amMCO - MIA
Nonstop1h 14mAmerican Airlines
Sat 6/712:04 pmMIA - MCO
Nonstop1h 11mAmerican Airlines
Deal found 4/29$132
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.
Tue 5/207:10 amMCO - MIA
Nonstop1h 12mDelta
Wed 5/218:05 pmMIA - MCO
Nonstop1h 16mDelta
Deal found 4/29$133
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2610:55 amMCO - MIA
Nonstop1h 10mSouthwest
Tue 9/2311:45 amMIA - MCO
1 stop8h 15mSouthwest
Deal found 4/29$143
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/256:07 amMCO - MIA
1 stop7h 09mSpirit Airlines
Tue 5/2710:29 amMIA - MCO
1 stop6h 10mSpirit Airlines
Deal found 4/29$161
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/147:05 amMCO - MIA
1 stop11h 43mFrontier
Sat 6/216:00 amMIA - MCO
1 stop23h 44mFrontier
Deal found 4/29$165
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:45 amMCO - MIA
1 stop14h 14mMultiple Airlines
Fri 6/202:23 pmMIA - MCO
1 stop18h 22mMultiple Airlines
Deal found 4/29$228
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2912:02 pmMCO - EYW
Nonstop1h 15mMultiple Airlines
Thu 7/34:20 pmEYW - MCO
2 stops28h 04mMultiple Airlines
Deal found 4/29$256
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/106:00 amMCO - MIA
1 stop7h 13mJetBlue
Tue 6/172:34 pmMIA - MCO
1 stop9h 52mJetBlue
Deal found 4/29$263
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/249:59 amMCO - EYW
1 stop3h 01mAmerican Airlines
Sat 5/317:29 pmEYW - MCO
1 stop4h 25mAmerican Airlines
Deal found 4/29$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.
Mon 9/158:59 pmMCO - EYW
2 stops14h 00mDelta
Fri 9/192:35 pmEYW - MCO
2 stops18h 52mDelta
Deal found 4/29$415

Cheapflights Fare Finder

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 April 30, 2025.
Use the filters below to find and compare flights from Kissimmee to Florida Keys that are best for you.

Fly from

Kissimmee

Fly to

Florida Keys

Route

Depart

Return

Price

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 6/22

12:02 pm-1:17 pm

Nonstop1h 15m

Key West

Fri 6/27

10:12 am-11:22 am

Nonstop1h 10m

$109

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sat 6/7

7:55 am-9:09 am

Nonstop1h 14m

Miami

Sat 6/7

12:04 pm-1:15 pm

Nonstop1h 11m

$132

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 5/20

7:10 am-8:22 am

Nonstop1h 12m

Miami

Wed 5/21

8:05 pm-9:21 pm

Nonstop1h 16m

$133

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 5/20

8:40 am-4:15 pm

1 stop7h 35m

Miami

Wed 5/21

7:15 am-1:10 pm

1 stop5h 55m

$153

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sun 5/25

6:07 am-1:16 pm

1 stop7h 09m

Miami

Tue 5/27

10:29 am-4:39 pm

1 stop6h 10m

$161

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Sat 6/14

7:05 am-6:48 pm

1 stop11h 43m

Miami

Sat 6/21

6:00 am-5:44 am

1 stop23h 44m

$165

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Fri 6/13

9:45 am-11:59 pm

1 stop14h 14m

Miami

Fri 6/20

2:23 pm-8:45 am

1 stop18h 22m

$228

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sun 6/29

12:02 pm-1:17 pm

Nonstop1h 15m

Key West

Thu 7/3

4:20 pm-8:24 pm

2 stops28h 04m

$256

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

Tue 6/10

6:00 am-1:13 pm

1 stop7h 13m

Miami

Tue 6/17

2:34 pm-12:26 am

1 stop9h 52m

$263

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

Sat 5/24

9:59 am-1:00 pm

1 stop3h 01m

Key West

Sat 5/31

7:29 pm-11:54 pm

1 stop4h 25m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 24 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Kissimmee to Florida Keys

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 $493). 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 April 30, 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.

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 April 30, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest and Delta 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.
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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!
Southwest
8.0
Very good
4,295 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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
7,929 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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!
Avelo Airlines
7.5
Good
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.1

Boarding

8.3

Food

6.7

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 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 $67. However, be on the lookout for offers from American Airlines and Breeze Airways, 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 (39%), JetBlue (39%) and Avianca (39%).

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

    The cheapest flight price from Kissimmee to Florida Keys is $40. On average you can expect to pay $91. The most popular route, (Orlando - Miami), can usually be booked for $109.

  • 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 $493). 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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Alternative routes for Kissimmee to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Kissimmee to Florida Keys

Discover the top 6 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 April 30, 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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