$119 Find Cheap Flights from Hilton Head Island to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Florida Keys departing on 1/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Florida Keys, as well as popular online travel agencies
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Flight Deals

Book Cheap Hilton Head Island to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Florida Keys that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Florida Keys

Tue, Nov 11 - Sat, Nov 15
American Airlines Logo
7:07 pm - 11:49 pmHHH-MIA
4h 42m1 stop
American Airlines Logo
6:00 am - 11:16 amMIA-HHH
5h 16m1 stop
$267American Airlines
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Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
6:07 pm - 12:26 amHHH-MIA
6h 19m1 stop
American Airlines Logo
6:00 am - 10:14 amMIA-HHH
4h 14m1 stop
$343American Airlines
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Fri, Nov 21 - Sat, Nov 29
American Airlines Logo
2:51 pm - 8:57 pmHHH-MIA
6h 06m1 stop
American Airlines Logo
6:00 am - 12:05 pmMIA-HHH
6h 05m1 stop
$431American Airlines
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Thu, Dec 25 - Mon, Dec 29
American Airlines Logo
2:46 pm - 7:04 amHHH-MIA
16h 18m2 stops
American Airlines Logo
6:00 am - 10:44 amMIA-HHH
4h 44m1 stop
$485American Airlines
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Thu, Dec 25 - Mon, Dec 29
American Airlines Logo
2:46 pm - 7:04 amHHH-MIA
16h 18m2 stops
American Airlines Logo
6:00 am - 10:44 amMIA-HHH
4h 44m1 stop
$488American Airlines
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Sat, Nov 22 - Sat, Nov 29
American Airlines Logo
6:40 pm - 9:09 amHHH-MIA
14h 29m2 stops
American Airlines Logo
6:00 am - 12:05 pmMIA-HHH
6h 05m1 stop
$489American Airlines
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Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
11:02 am - 8:20 pmHHH-MIA
9h 18m2 stops
American Airlines Logo
6:00 am - 10:14 amMIA-HHH
4h 14m1 stop
$521American Airlines
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Thu, Dec 25 - Mon, Dec 29
American Airlines Logo
11:14 am - 3:23 pmHHH-MIA
4h 09m1 stop
American Airlines Logo
6:00 am - 10:44 amMIA-HHH
4h 44m1 stop
$547American Airlines
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Thu, Dec 25 - Mon, Dec 29
American Airlines Logo
11:14 am - 3:23 pmHHH-MIA
4h 09m1 stop
American Airlines Logo
6:00 am - 10:44 amMIA-HHH
4h 44m1 stop
$557American Airlines
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Fri, Nov 21 - Sat, Nov 29
American Airlines Logo
6:40 pm - 9:09 amHHH-MIA
14h 29m2 stops
American Airlines Logo
6:00 am - 12:05 pmMIA-HHH
6h 05m1 stop
$580American Airlines
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Booking Insights

KAYAK's insights & trends for Hilton Head Island to Florida Keys flights

Get data-powered insights and trends into flights from Hilton Head Island to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Hilton Head Island to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $510 on average.

What’s the cheapest day of the week to fly from Hilton Head Island to Florida Keys?

The average price of all round-trip flights from Hilton Head Island to Florida Keys clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Hilton Head Island to Florida Keys, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Florida Keys, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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Good to know

Cheapest flight$119
Flight from Hilton Head Island to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Hilton Head Island to Florida Keys?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hilton Head Island to Florida Keys is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Florida Keys?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Hilton Head Island to Florida Keys with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Florida Keys?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Hilton Head Island to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida Keys?

    The cheapest time of day to fly to Florida Keys is generally in the morning, when round-trip flights cost $455 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $607.

Reviews of the top airline flying from Hilton Head Island to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Florida Keys? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11030 reviews
6.4Food
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
Airline reviews

Delays to take off and to leave the plane after landing added a lot of time to this flight.

6.0 GoodMiguel, Oct 2025PHL - MIA
Read more American Airlines reviews

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

Hilton Head Island (HHH)

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