Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travelers

KAYAK searches hundreds of travel sites at once for vacation package deals in Hilton Head Island

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Bundle and saveSave money when you bundle your flight + hotel.

Search
Best Deals
Tips
Vacation information

Cheap Hilton Head Island package deals

Discover the best prices by selecting your travel dates on KAYAK.
Go to map

Search by stars

2+ stars3+ stars4+ stars

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by board

BreakfastHalf boardSelf cateringAll inclusiveMeals not included

Search by price

$368 - $921$921 - $1,475$1,475 - $2,028$2,028 - $2,582$2,582+ per night

Search by freebies

Free breakfastFree internetFree airport shuttleFree parking

Most popular Hilton Head Island flight and hotel deals

Show all
Courtyard by Marriott Hilton Head Island - Hilton Head Island - Patio
Courtyard by Marriott Hilton Head Island - Hilton Head Island - Patio
Courtyard by Marriott Hilton Head Island
8.6 Very good
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$508
Spark by Hilton Hilton Head Island - Hilton Head Island - Bedroom
Spark by Hilton Hilton Head Island - Hilton Head Island - Bedroom
Spark by Hilton Hilton Head Island
8.1 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Madison Truax Field
Meals not included
3 nights + flight
$403
Marriott's Surf Watch, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Surf Watch, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Surf Watch, A Marriott Vacation Club Resort
9.7 Wonderful
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$896
Palmera Inn and Suites - Hilton Head Island - Living room
Palmera Inn and Suites - Hilton Head Island - Living room
Palmera Inn and Suites
8.6 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Madison Truax Field
Meals not included
3 nights + flight
$462
Beach House Resort Hilton Head Island - Hilton Head Island - Bar
Beach House Resort Hilton Head Island - Hilton Head Island - Bar
Beach House Resort Hilton Head Island
8.1 Very good
Pool
Pet friendly
Madison Truax Field
Meals not included
3 nights + flight
$579
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Lounge
Hilton Beachfront Resort and Spa Hilton Head Island - Hilton Head Island - Lounge
Hilton Beachfront Resort and Spa Hilton Head Island
7.9 Good
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$638
Marriott's Harbour Point and Sunset Pointe at Shelter Cove, A Marriott Vacation Club Resort - Hilton Head Island - Patio
Marriott's Harbour Point and Sunset Pointe at Shelter Cove, A Marriott Vacation Club Resort - Hilton Head Island - Patio
Marriott's Harbour Point and Sunset Pointe at Shelter Cove, A Marriott Vacation Club Resort
8.2 Very good
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$673
Home2 Suites by Hilton Hilton Head - Hilton Head Island - Patio
Home2 Suites by Hilton Hilton Head - Hilton Head Island - Patio
Home2 Suites by Hilton Hilton Head
8.8 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Madison Truax Field
Breakfast
3 nights + flight
$461
Sonesta Resort Hilton Head Island - Hilton Head Island - Pool
Sonesta Resort Hilton Head Island - Hilton Head Island - Pool
Sonesta Resort Hilton Head Island
8.4 Very good
Pool
Pet friendly
Spa
Las Vegas Harry Reid Intl
Meals not included
3 nights + flight
$613
Luxury Penthouse near Beach Tiki Hut Coligny - Hilton Head Island - Bedroom
Luxury Penthouse near Beach Tiki Hut Coligny - Hilton Head Island - Bedroom
Luxury Penthouse near Beach Tiki Hut Coligny
9.8 Wonderful
Parking
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$778
Hilton Grand Vacations Club Ocean Oak Resort Hilton Head - Hilton Head Island - Pool
Hilton Grand Vacations Club Ocean Oak Resort Hilton Head - Hilton Head Island - Pool
Hilton Grand Vacations Club Ocean Oak Resort Hilton Head
9 Wonderful
Pool
Madison Truax Field
Meals not included
3 nights + flight
$1,058
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head - Hilton Head Island - Pool
Hampton Inn Hilton Head
8.3 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
Madison Truax Field
Breakfast
3 nights + flight
$432
Marriott's Grande Ocean, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Grande Ocean, A Marriott Vacation Club Resort - Hilton Head Island - Pool
Marriott's Grande Ocean, A Marriott Vacation Club Resort
9.1 Wonderful
Free Wi-Fi
Pool
Spa
Madison Truax Field
Meals not included
3 nights + flight
$1,148
Hilton Head Condo Close to Beach & Golfing condo - Hilton Head Island - Living room
Hilton Head Condo Close to Beach & Golfing condo - Hilton Head Island - Living room
Hilton Head Condo Close to Beach & Golfing condo
Parking
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$775
Holiday Inn Express Hilton Head Island By IHG - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island By IHG - Hilton Head Island - Bedroom
Holiday Inn Express Hilton Head Island By IHG
7.7 Good
Free Wi-Fi
Pool
Pet friendly
Madison Truax Field
Breakfast
3 nights + flight
$484
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Living room
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Living room
Hilton Head Island Beach & Tennis Resort
7.9 Good
Free Wi-Fi
Pool
Madison Truax Field
Meals not included
3 nights + flight
$673

When to book a vacation in Hilton Head Island

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Hilton Head Island package deals

  • There are loads of types of vacations in Hilton Head Island and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $348; Family vacation $258; Luxury vacation $515; Budget vacation $368.

Where to stay in Hilton Head Island

Our map will help you find the perfect place to stay for your vacation in Hilton Head Island by showing you the exact location of each hotel.

Everything you need to know for your vacation in Hilton Head Island

Hilton Head Island vacation information

Top vacation (Flight+Hotel)$348
Family vacation (Flight+Hotel)$258
Luxury vacation (Flight+Hotel)$515
Budget vacation (Flight+Hotel)$368