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Hilton Head Island

$242+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
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 May 21, 2026.

This American Airlines deal was found by Cheapflights users on 5/16. 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.
Thu 7/910:03 am
MCO
-
HHH
1 stop6h 22m
American Airlines
Sun 7/124:55 pm
HHH
-
MCO
1 stop5h 05m
American Airlines
Deal found 5/16$367
This American Airlines deal was found by Cheapflights users on 5/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
MCO
-
HHH
2 stops8h 16m
American Airlines
Mon 7/132:48 pm
HHH
-
MCO
1 stop3h 56m
American Airlines
Deal found 5/20$372
This American Airlines deal was found by Cheapflights users on 5/16. 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 7/19:00 am
MCO
-
HHH
1 stop5h 13m
American Airlines
Wed 7/811:47 am
HHH
-
MCO
1 stop4h 57m
American Airlines
Deal found 5/16$379
This American Airlines deal was found by Cheapflights users on 5/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/199:00 am
MCO
-
HHH
1 stop5h 13m
American Airlines
Fri 6/265:21 pm
HHH
-
MCO
1 stop4h 39m
American Airlines
Deal found 5/20$426
This American Airlines deal was found by Cheapflights users on 5/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:03 am
MCO
-
HHH
1 stop6h 22m
American Airlines
Fri 7/3111:47 am
HHH
-
MCO
1 stop5h 49m
American Airlines
Deal found 5/20$428
This American Airlines deal was found by Cheapflights users on 5/19. 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 11/41:55 pm
MCO
-
HHH
1 stop4h 14m
American Airlines
Sat 11/76:40 pm
HHH
-
MCO
1 stop5h 44m
American Airlines
Deal found 5/19$447
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Mon 6/156:15 am
MCO
-
HHH
1 stop4h 55m
American Airlines
Sun 6/215:21 pm
HHH
-
MCO
1 stop4h 39m
American Airlines
Deal found 5/16$483

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 May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(American Airlines)

One-way from

$242
(American Airlines)
Provider with most accurate pricing for Orlando (ORL)-Hilton Head Island flight deals.
Search Deals
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 May 21, 2026.
Use the filters below to find and compare flights from Kissimmee to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 7/10

10:03 am-2:16 pm

1 stop4h 13m

Hilton Head Island

Mon 7/13

4:55 pm-9:00 pm

1 stop4h 05m

$367

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 7/1

9:00 am-2:13 pm

1 stop5h 13m

Hilton Head Island

Wed 7/8

11:47 am-4:44 pm

1 stop4h 57m

$379

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 6/15

6:15 am-11:10 am

1 stop4h 55m

Hilton Head Island

Sun 6/21

5:21 pm-10:00 pm

1 stop4h 39m

$483

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 11/4

6:00 am-2:19 pm

2 stops8h 19m

Hilton Head Island

Sat 11/7

6:40 pm-12:24 am

1 stop5h 44m

$531

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 7/3

11:05 am-3:32 pm

1 stop4h 27m

Hilton Head Island

Mon 7/6

12:13 pm-6:44 pm

1 stop6h 31m

$539

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 11/6

10:03 am-6:09 pm

2 stops8h 06m

Hilton Head Island

Sat 11/7

6:40 pm-12:24 am

1 stop5h 44m

$684

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 8/28

6:00 pm-2:03 pm

1 stop20h 03m

Hilton Head Island

Tue 9/1

2:48 pm-6:10 pm

3 stops27h 22m

$724
Cheapest one-way

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 6/13

5:00 am-11:10 am

1 stop6h 10m

$242

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 6/13

3:17 pm-2:21 pm

2 stops23h 04m

$435
Quickest one-way

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 6/5

11:00 am-3:33 pm

1 stop4h 33m

$600

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

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
No data available for this route at this time. Please check back soon.

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 13m. 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.

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 May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$365FlexibilityNo cancel feeOn-time71%

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