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Hilton Head Island

$174+ Cheap flights from Kissimmee, FL to Hilton Head Island (HHH)

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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Kissimmee to Hilton Head Island

Cheapest flights from Kissimmee to Hilton Head Island
Explore the most affordable flight options available from Kissimmee to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This American Airlines deal was found by Cheapflights users on 2/12. 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 8/86:15 am
MCO
-
HHH
1 stop5h 15m
American Airlines
Sat 8/152:42 pm
HHH
-
MCO
1 stop4h 02m
American Airlines
Deal found 2/12$377
This American Airlines deal was found by Cheapflights users on 2/10. 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 7/46:12 am
MCO
-
HHH
1 stop4h 58m
American Airlines
Sat 7/115:54 pm
HHH
-
MCO
1 stop4h 06m
American Airlines
Deal found 2/10$410
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Sun 8/97:10 am
MCO
-
HHH
1 stop7h 02m
American Airlines
Sat 8/156:15 pm
HHH
-
MCO
1 stop5h 51m
American Airlines
Deal found 2/12$430
This American Airlines deal was found by Cheapflights users on 2/12. 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 2/286:00 am
MCO
-
HHH
1 stop4h 33m
American Airlines
Wed 3/43:31 pm
HHH
-
MCO
1 stop5h 25m
American Airlines
Deal found 2/12$465
This American Airlines deal was found by Cheapflights users on 2/10. 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 4/115:00 am
MCO
-
HHH
1 stop5h 32m
American Airlines
Mon 4/206:39 pm
HHH
-
MCO
1 stop5h 35m
American Airlines
Deal found 2/10$468
This American Airlines deal was found by Cheapflights users on 2/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:33 am
MCO
-
HHH
1 stop5h 11m
American Airlines
Sun 3/12:58 pm
HHH
-
MCO
1 stop7h 01m
American Airlines
Deal found 2/9$507
This American Airlines deal was found by Cheapflights users on 2/12. 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.
Fri 2/276:00 am
MCO
-
HHH
2 stops11h 44m
American Airlines
Tue 3/312:23 pm
HHH
-
MCO
2 stops9h 37m
American Airlines
Deal found 2/12$517

Find flight deals from Kissimmee to Hilton Head Island

Keep the following information in mind while searching for Kissimmee to Hilton Head Island flight deals. Data was last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$465
(American Airlines)

One-way from

$174
(American Airlines)
Provider with most accurate pricing for Orlando (ORL)-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Hilton Head Island flights.
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From Kissimmee to Hilton Head Island
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One-way flight from Kissimmee to Hilton Head Island
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Hilton Head Island 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 13, 2026.
Use the filters below to find and compare flights from Kissimmee to Hilton Head Island that are best for you.

Fly from

Kissimmee

Fly to

Hilton Head Island

Route

Depart

Return

Price

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 2/28

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Wed 3/4

3:31 pm-8:56 pm

1 stop5h 25m

$465

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 4/11

5:00 am-10:32 am

1 stop5h 32m

Hilton Head Island

Mon 4/20

6:39 pm-12:14 am

1 stop5h 35m

$468

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 2/25

11:33 am-4:44 pm

1 stop5h 11m

Hilton Head Island

Sun 3/1

2:58 pm-9:59 pm

1 stop7h 01m

$507

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 2/27

5:00 am-10:33 am

1 stop5h 33m

Hilton Head Island

Tue 3/3

12:23 pm-5:13 pm

1 stop4h 50m

$507

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Thu 2/26

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Mon 3/2

11:03 am-4:47 pm

1 stop5h 44m

$549

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Thu 3/26

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Sun 3/29

2:58 pm-8:46 pm

1 stop5h 48m

$553

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 5/12

10:00 am-2:24 pm

1 stop4h 24m

$174

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 3/17

7:00 am-11:53 am

1 stop4h 53m

$174

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 4/25

9:19 pm-3:14 pm

1 stop17h 55m

$259

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 2/27

9:27 pm-4:01 pm

1 stop18h 34m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 13 results
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Best time to book a flight from Kissimmee to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island 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 Hilton Head Island

What is the cheapest month to book a flight from Kissimmee to Hilton Head Island?

Currently, February is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $63). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $120). 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.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Hilton Head Island. 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 Hilton Head Island from Kissimmee?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Kissimmee to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Kissimmee; the airport handles an average of 0 inbound flights from Kissimmee per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Hilton Head Island airport from Kissimmee. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

  • How long is the flight from Kissimmee to Hilton Head Island?

    Departing from Kissimmee to Hilton Head Island will take you 4h 33m. Airlines will cover a distance of 264 mi.

  • Can I find deals for flights from Kissimmee to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Kissimmee to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kissimmee to Hilton Head Island?

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

  • Can I find deals for business class flights from Kissimmee to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Kissimmee to Hilton Head Island 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 Hilton Head Island?

    Currently, February is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $63). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $120). 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

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Top airline flying from Kissimmee to Hilton Head Island

Discover the top airline that operate flights from Kissimmee to Hilton Head Island. 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 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$346FlexibilityNo cancel feeOn-time71%

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