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

$396 - $1,124$1,124 - $1,853$1,853 - $2,582$2,582 - $3,311$3,311+ 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
8.7 Very good
Free Wi-Fi
Pool
Fort Lauderdale
Meals not included
3 nights + flight
$501
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
Fort Lauderdale
Meals not included
3 nights + flight
$421
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
9.9 Wonderful
Free Wi-Fi
Pool
Dallas/Fort Worth
Meals not included
3 nights + flight
$728
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
Fort Lauderdale
Meals not included
3 nights + flight
$475
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
Fort Lauderdale
Meals not included
3 nights + flight
$666
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Restaurant
The Westin Hilton Head Island Resort & Spa - Hilton Head Island - Restaurant
The Westin Hilton Head Island Resort & Spa
8.6 Very good
Free Wi-Fi
Pool
Pet friendly
Spa
Fort Lauderdale
Meals not included
3 nights + flight
$608
Hilton Garden Inn Hilton Head - Hilton Head Island - Patio
Hilton Garden Inn Hilton Head - Hilton Head Island - Patio
Hilton Garden Inn Hilton Head
8.3 Very good
Parking
Pool
Pet friendly
Fort Lauderdale
Meals not included
3 nights + flight
$483
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
Fort Lauderdale
Breakfast
3 nights + flight
$482
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
Fort Lauderdale
Meals not included
3 nights + flight
$553
Xanadu A1 - Hilton Head Island - Beach
Xanadu A1 - Hilton Head Island - Beach
Xanadu A1
8.2 Very good
Parking
Free Wi-Fi
Pool
Chicago O'Hare Intl
Meals not included
3 nights + flight
$818
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
Fort Lauderdale
Breakfast
3 nights + flight
$464
Bluewater by Spinnaker Resorts - Hilton Head Island - Building
Bluewater by Spinnaker Resorts - Hilton Head Island - Building
Bluewater by Spinnaker Resorts
9 Wonderful
Parking
Free Wi-Fi
Pool
Fort Lauderdale
Meals not included
3 nights + flight
$632
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
9.4 Wonderful
Free Wi-Fi
Pool
Spa
Dallas/Fort Worth
Meals not included
3 nights + flight
$708
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
7.8 Good
Free Wi-Fi
Pool
Pet friendly
Fort Lauderdale
Breakfast
3 nights + flight
$466
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort - Hilton Head Island - Pool
Omni Hilton Head Oceanfront Resort
8.5 Very good
Pool
Pet friendly
Spa
Fort Lauderdale
Meals not included
3 nights + flight
$670
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
Fort Lauderdale
Meals not included
3 nights + flight
$665

Last minute vacation packages to Hilton Head Island

Show all
5 Fazio Villas - Hilton Head Island
5 Fazio Villas - Hilton Head Island
5 Fazio Villas
Parking
Free Wi-Fi
Pool
Grand Rapids Gerald R. Ford Intl
Meals not included
3 nights + flight
$1,066
418 Captain's Walk - Hilton Head Island - Pool
418 Captain's Walk - Hilton Head Island - Pool
418 Captain's Walk
7 Good
Parking
Free Wi-Fi
Pool
Grand Rapids Gerald R. Ford Intl
Meals not included
3 nights + flight
$1,419
293 Turnberry Village - Hilton Head Island
293 Turnberry Village - Hilton Head Island
293 Turnberry Village
Parking
Free Wi-Fi
Pool
Grand Rapids Gerald R. Ford Intl
Meals not included
3 nights + flight
$979
477 Captain's Walk - Hilton Head Island
477 Captain's Walk - Hilton Head Island
477 Captain's Walk
Parking
Free Wi-Fi
Pool
Grand Rapids Gerald R. Ford Intl
Meals not included
3 nights + flight
$1,320

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