Vacations in Hilton Head Island

Vacations in Hilton Head Island

2 travelers

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Cheap Hilton Head Island package deals

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$235 - $947$947 - $1,658$1,658 - $2,369$2,369 - $3,080$3,080+ per night

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Most popular Hilton Head Island flight and hotel deals

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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
8.9 Very good
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$392
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
7.9 Good
Parking
Free Wi-Fi
Pool
Pet friendly
Cincinnati Cinci./N. Kentucky
Breakfast
3 nights + flight
$281
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
Cincinnati Cinci./N. Kentucky
Breakfast
3 nights + flight
$356
Beach House Resort Hilton Head - Hilton Head Island - Restaurant
Beach House Resort Hilton Head - Hilton Head Island - Restaurant
Beach House Resort Hilton Head
8 Very good
Pool
Pet friendly
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$425
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
8 Very good
Free Wi-Fi
Pool
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$371
Hotel Carolina A Days Inn by Wyndham - Hilton Head Island - Building
Hotel Carolina A Days Inn by Wyndham - Hilton Head Island - Building
Hotel Carolina A Days Inn by Wyndham
6.4 Okay
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$272
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
Cincinnati Cinci./N. Kentucky
Breakfast
3 nights + flight
$361
Sonesta Resort Hilton Head Island - Hilton Head Island - Bedroom
Sonesta Resort Hilton Head Island - Hilton Head Island - Bedroom
Sonesta Resort Hilton Head Island
8.3 Very good
Pool
Pet friendly
Spa
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$447
Coral Sands Resort by Palmera - Hilton Head Island - Living room
Coral Sands Resort by Palmera - Hilton Head Island - Living room
Coral Sands Resort by Palmera
8.7 Very good
Parking
Free Wi-Fi
Pool
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$414
Island Links Resort by Palmera - Hilton Head Island - Pool
Island Links Resort by Palmera - Hilton Head Island - Pool
Island Links Resort by Palmera
9 Wonderful
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$539
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
Cincinnati Cinci./N. Kentucky
Breakfast
3 nights + flight
$312
245 Stoney Creek Villa at The Sea Pines Resort - Hilton Head Island - Restaurant
245 Stoney Creek Villa at The Sea Pines Resort - Hilton Head Island - Restaurant
245 Stoney Creek Villa at The Sea Pines Resort
Parking
Free Wi-Fi
Pool
Boston Logan Intl
Meals not included
3 nights + flight
$795
The Village Palmetto Dunes - Hilton Head Island
The Village Palmetto Dunes - Hilton Head Island
The Village Palmetto Dunes
8.5 Very good
Parking
Free Wi-Fi
Pool
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$557
Simple Rewards Inn - Hilton Head Island - Bedroom
Simple Rewards Inn - Hilton Head Island - Bedroom
Simple Rewards Inn
8.3 Very good
Parking
Free Wi-Fi
Pet friendly
Boston Logan Intl
Meals not included
3 nights + flight
$310
Red Roof Inn Hilton Head Island - Hilton Head Island - Bedroom
Red Roof Inn Hilton Head Island - Hilton Head Island - Bedroom
Red Roof Inn Hilton Head Island
6 Okay
Parking
Free Wi-Fi
Pool
Pet friendly
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$235
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Pool
Hilton Head Island Beach & Tennis Resort - Hilton Head Island - Pool
Hilton Head Island Beach & Tennis Resort
7.9 Good
Free Wi-Fi
Pool
Cincinnati Cinci./N. Kentucky
Meals not included
3 nights + flight
$493

Last minute vacation packages to Hilton Head Island

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2248 Heritage Villas at The Sea Pines Resort - Hilton Head Island - Restaurant
2248 Heritage Villas at The Sea Pines Resort - Hilton Head Island - Restaurant
2248 Heritage Villas at The Sea Pines Resort
Parking
Free Wi-Fi
Pool
Memphis
Meals not included
3 nights + flight
$1,204
149 Harbourwood Villa at The Sea Pines Resort - Hilton Head Island - Beach
149 Harbourwood Villa at The Sea Pines Resort - Hilton Head Island - Beach
149 Harbourwood Villa at The Sea Pines Resort
Parking
Free Wi-Fi
Pool
Memphis
Meals not included
3 nights + flight
$1,256
Marriott's Heritage Club, A Marriott Vacation Club Resort - Hilton Head Island - Lounge
Marriott's Heritage Club, A Marriott Vacation Club Resort - Hilton Head Island - Lounge
Marriott's Heritage Club, A Marriott Vacation Club Resort
8 Very good
Harbour Town
Free Wi-Fi
Pool
Rochester Greater Rochester Intl
Meals not included
3 nights + flight
$1,046

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

Hilton Head Island vacation: Search Hilton Head Island vacation packages on KAYAK. KAYAK is a travel tool that searches Hilton Head Island trips on hundreds of travel sites to help you find the Hilton Head Island package that suits you best. Discover Hilton Head Island deals now and book your Hilton Head Island flight and hotel today.

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