$287 Find Cheap Flights from Hilton Head Island to Florida Keys - Compare and Save

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 8/9. 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, Jul 14 - Wed, Jul 22
Delta Logo
12:11 pm - 6:20 pm
HHH
-
MIA
6h 09m
1 stop
Delta Logo
8:20 am - 3:29 pm
MIA
-
HHH
7h 09m
1 stop
$347Delta
Tue, Jul 14 - Thu, Jul 23
Delta Logo
12:11 pm - 4:55 pm
HHH
-
MIA
4h 44m
1 stop
Delta Logo
10:40 am - 3:29 pm
MIA
-
HHH
4h 49m
1 stop
$357Delta
Tue, Jul 14 - Sat, Jul 25
Delta Logo
12:11 pm - 4:55 pm
HHH
-
MIA
4h 44m
1 stop
Delta Logo
8:30 pm - 3:29 pm
MIA
-
HHH
18h 59m
1 stop
$391Delta
Tue, Jul 14 - Mon, Jul 27
Delta Logo
12:11 pm - 6:20 pm
HHH
-
MIA
6h 09m
1 stop
Delta Logo
6:00 am - 3:29 pm
MIA
-
HHH
9h 29m
1 stop
$397Delta
Thu, Jul 16 - Thu, Jul 23
Delta Logo
12:11 pm - 6:20 pm
HHH
-
MIA
6h 09m
1 stop
Delta Logo
10:40 am - 3:29 pm
MIA
-
HHH
4h 49m
1 stop
$407Delta
Tue, Jul 14 - Sun, Jul 26
Delta Logo
12:11 pm - 6:20 pm
HHH
-
MIA
6h 09m
1 stop
Delta Logo
6:00 am - 3:29 pm
MIA
-
HHH
9h 29m
1 stop
$416Delta
Fri, Jul 10 - Sun, Jul 12
Delta Logo
12:11 pm - 7:25 pm
HHH
-
MIA
7h 14m
1 stop
Delta Logo
8:20 am - 3:29 pm
MIA
-
HHH
7h 09m
1 stop
$417Delta
Tue, Jul 14 - Thu, Jul 23
Delta Logo
12:11 pm - 10:26 am
HHH
-
MIA
22h 15m
2 stops
Delta Logo
10:40 am - 3:29 pm
MIA
-
HHH
4h 49m
1 stop
$423Delta
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
2:48 pm - 8:21 pm
HHH
-
MIA
5h 33m
1 stop
American Airlines Logo
8:40 am - 3:04 pm
MIA
-
HHH
6h 24m
1 stop
$447American Airlines
Fri, Jul 10 - Tue, Jul 14
American Airlines Logo
2:03 pm - 3:42 pm
HHH
-
EYW
25h 39m
1 stop
American Airlines Logo
4:18 pm - 1:33 pm
EYW
-
HHH
21h 15m
1 stop
$755American Airlines
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.

No, with an average price for the route of $495, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$287
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.

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.
7.1
American AirlinesOverall score based on 11757 reviews
7.5Boarding
6.8Entertainment
7.2Comfort
7.9Crew
6.4Food
Airline reviews

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

10.0 ExcellentAnonymous, Jun 2026
LGA - MIA
Read more American Airlines reviews

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Would have thought that they would gas up plane before everyone got on board

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports