In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

What is the cheapest time of day to fly from HHH to EYW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Hilton Head Island to Key West as you normally would.

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

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

How can I find direct flights from Hilton Head Island to Key West?

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

Can I find deals for business class flights from Hilton Head Island to Key West?

Yes. Cheapflights offers flight deals from Hilton Head Island to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$427+ Flights from Hilton Head Island to Key West

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Cheap flight deals from Hilton Head Island to Key West

Round-trip from	$427 (Delta)

From Hilton Head Island to Key West

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Find flight deals from Hilton Head Island to Key West

Cheapest flights from Hilton Head Island to Key West
Explore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

mar. 8/2612:11 pmHHH - EYW

1 stop5h 01mDelta

sáb. 8/306:20 pmEYW - HHH

1 stop21h 02mDelta

Deal found 7/28

$427

vie. 10/312:56 pmHHH - EYW

1 stop4h 50mAmerican Airlines

mar. 10/75:47 pmEYW - HHH

2 stops18h 25mAmerican Airlines

Deal found 7/30

$516

Best flights from Hilton Head Island to Key West
Discover carefully curated flight deals from Hilton Head Island to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated julio 30, 2025.

mar. 8/2612:11 pmHHH - EYW

1 stop5h 01mDelta

sáb. 8/306:20 pmEYW - HHH

1 stop21h 02mDelta

Deal found 7/28

$427

vie. 10/312:56 pmHHH - EYW

1 stop4h 50mAmerican Airlines

mar. 10/75:47 pmEYW - HHH

2 stops18h 25mAmerican Airlines

Deal found 7/30

$516

Last-minute flights from Hilton Head Island to Key West
Discover last-minute flight deals from Hilton Head Island to Key West. Data last updated julio 30, 2025 and is based on user searches.

mar. 8/2612:11 pmHHH - EYW

1 stop5h 01mDelta

sáb. 8/306:20 pmEYW - HHH

1 stop21h 02mDelta

Deal found 7/28

$427

mar. 8/2612:29 pmHHH - EYW

2 stops6h 38mAmerican Airlines

sáb. 8/307:40 pmEYW - HHH

2 stops18h 32mAmerican Airlines

Deal found 7/28

$586

Cheapflights Fare Finder

Use the filters below to find and compare flights from Hilton Head Island to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

mar. 8/26

12:11 pm-5:12 pm

1 stop5h 01m

Key West

sáb. 8/30

6:20 pm-3:22 pm

1 stop21h 02m

$427

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

vie. 10/3

12:56 pm-5:46 pm

1 stop4h 50m

Key West

mar. 10/7

5:47 pm-12:12 pm

2 stops18h 25m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Hilton Head Island to Key West

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

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

Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $328). Flying from Hilton Head Island to Key West in March is currently the most expensive (average of $492). 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.

Reviews of airlines servicing Key West

Read through reviews of airlines operating flights from Hilton Head Island to Key West, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

CAE - ATL

On time flights; courteous staff; efficient boarding system! Thank you!

Delta

8.0

Very good

7,980 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

CAE - ATL

On time flights; courteous staff; efficient boarding system! Thank you!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,980 reviews

Reviews

1 / 20

10.0

Excellent

Lucy,Nov 2023

CAE - ATL

On time flights; courteous staff; efficient boarding system! Thank you!

Related info for your journey

Can I find deals for flights from Hilton Head Island to Key West that include hotel bookings?
Yes. In addition to deals on Hilton Head Island to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Hilton Head Island to Key West?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Key West.
Can I find deals for business class flights from Hilton Head Island to Key West?
Yes. Cheapflights offers flight deals from Hilton Head Island to Key West 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 Hilton Head Island to Key West?
Currently, August is the cheapest month in which you can book a flight from Hilton Head Island to Key West (average of $328). Flying from Hilton Head Island to Key West in March is currently the most expensive (average of $492). 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

Browse thousands of different options on Cheapflights for your next trip

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$427+ Cheap flights from Hilton Head Island to Key West (HHH - EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Hilton Head Island to Key West with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Hilton Head Island to Key West

Round-trip from

Find flight deals from Hilton Head Island to Key West

Cheapest flights from Hilton Head Island to Key WestExplore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

Explore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Hilton Head Island to Key West that are best for you.

Best time to book a flight from Hilton Head Island to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Hilton Head Island with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Hilton Head Island to Key West

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

Reviews of airlines servicing Key West

Read through reviews of airlines operating flights from Hilton Head Island to Key West, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

How can I find direct flights from Hilton Head Island to Key West?

Can I find deals for business class flights from Hilton Head Island to Key West?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hilton Head Island to Key West

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Hilton Head Island to Key West
Explore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 30, 2025.