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Florida Keys

$38+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EYW
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheap 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 enero 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/28. 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.
vie. 2/2711:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
vie. 3/61:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/28$92
This Mytrip deal was found by Cheapflights users on 1/29. 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.
dom. 2/227:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 2/269:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/29$93
This Mytrip deal was found by Cheapflights users on 1/28. 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.
vie. 3/611:10 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 3/129:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/28$95
This Southwest deal was found by Cheapflights users on 1/27. 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.
mar. 2/2410:50 am
MCO
-
MIA
Nonstop1h 15m
Southwest
mar. 3/35:20 pm
MIA
-
MCO
Nonstop1h 15m
Southwest
Deal found 1/27$97
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
jue. 2/267:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 3/59:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/27$97
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
jue. 2/267:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
vie. 2/271:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/28$98
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
jue. 2/57:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 2/129:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/27$103
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
mié. 4/19:55 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
vie. 4/31:06 pm
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/27$104
This Mytrip deal was found by Cheapflights users on 1/28. 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.
mié. 3/189:55 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 3/199:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/28$105
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
dom. 2/227:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 3/269:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/28$106
This Southwest deal was found by Cheapflights users on 1/27. 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.
mar. 2/248:50 pm
MCO
-
MIA
Nonstop1h 10m
Southwest
sáb. 2/286:35 am
MIA
-
MCO
Nonstop1h 10m
Southwest
Deal found 1/27$107
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
dom. 2/87:50 am
MCO
-
EYW
Nonstop1h 16m
Breeze Airways
jue. 2/269:46 am
EYW
-
MCO
Nonstop1h 20m
Breeze Airways
Deal found 1/27$107

Find 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 enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$92
(Mytrip)

One-way from

$38
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$229
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. 19% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 enero 29, 2026.
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

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mié. 2/18

8:50 pm-10:00 pm

Nonstop1h 10m

Miami

mié. 2/25

5:20 pm-6:35 pm

Nonstop1h 15m

$97

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mié. 2/25

10:50 am-12:05 pm

Nonstop1h 15m

Miami

mié. 3/4

6:55 am-8:05 am

Nonstop1h 10m

$97

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mié. 2/18

10:50 am-12:05 pm

Nonstop1h 15m

Miami

mar. 2/24

6:55 am-8:05 am

Nonstop1h 10m

$97

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

jue. 2/26

7:50 am-9:06 am

Nonstop1h 16m

Key West

vie. 2/27

1:06 pm-2:26 pm

Nonstop1h 20m

$98

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mar. 3/3

10:50 am-12:05 pm

Nonstop1h 15m

Miami

jue. 3/5

6:15 am-7:30 am

Nonstop1h 15m

$107

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mar. 2/24

8:50 pm-10:00 pm

Nonstop1h 10m

Miami

mar. 3/3

12:55 pm-7:00 pm

1 stop6h 05m

$107

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

mié. 4/15

8:45 pm-9:55 pm

Nonstop1h 10m

Miami

mar. 4/21

7:20 am-4:00 pm

1 stop8h 40m

$107

OrlandoMiami

MCO - MIA

MCOMIA

Orlando

lun. 3/23

8:50 pm-10:05 pm

Nonstop1h 15m

Miami

mié. 3/25

5:35 pm-6:55 pm

Nonstop1h 20m

$107

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

mié. 4/29

9:55 am-11:11 am

Nonstop1h 16m

Key West

jue. 4/30

9:46 am-11:06 am

Nonstop1h 20m

$108

OrlandoKey West

MCO - EYW

MCOEYW

Orlando

jue. 6/4

10:10 am-11:25 am

Nonstop1h 15m

Key West

vie. 6/5

12:10 pm-1:26 pm

Nonstop1h 16m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 39 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, June is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $66). Flying from Kissimmee to Florida Keys in October is currently the most expensive (average of $99). 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 enero 29, 2026.

One of the essential ways to save on airfare from Kissimmee to Florida Keys 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 42% on airfare.

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 enero 29, 2026.
Read reviews from past customers who have flown Breeze Airways, Southwest, and United Airlines from Kissimmee to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,267 reviews
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,215 reviews
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,206 reviews
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Silver Airways
5.7
Fair
Breeze Airways
8.2
Very good
263 reviews

Food

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Entertainment

6.6

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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.

  • How long is the flight from Kissimmee to Florida Keys?

    For as low as $97, Southwest can have you in Florida Keys from Kissimmee in 1h 10m. The distance from Kissimmee to Florida Keys is about 192 mi. Generally, flights for this route are nonstop.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $36. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Kissimmee to Florida Keys for a low price.

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

    The cheapest flight price from Kissimmee to Florida Keys is $44. On average you can expect to pay $89. The most popular route, (Orlando - Miami), can usually be booked for $97.

  • 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, June is the cheapest month in which you can book a flight from Kissimmee to Florida Keys (average of $66). Flying from Kissimmee to Florida Keys in October is currently the most expensive (average of $99). 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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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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$43Average$161FlexibilityNo cancel feeOn-time69%
Allegiant AirCheapest$58Average$200FlexibilityNo cancel feeOn-time88%
Silver AirwaysCheapest$66Average$133FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$90Average$157FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$257FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$200Average$387FlexibilityNo cancel feeOn-time71%

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