Hilton Head, SC Vacations

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Featured Vacation Rentals

A beautiful home to help you create your...

This handsome near ocean Hilton Head home rental is just a 3-5 min. walk to the beach, has waterway and private pool vistas, handsome appointments and a great interior design to help you create a dream vacation.The downstairs features three living...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Large Golf Course View Home with Large P...

This charming home features opulent wide plank, hand-scraped, black walnut floor throughout the main living areas. This amazing home consists of six bedrooms, six and a half bathrooms along with an splendid sunroom along with a enchanting nook...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
8 Bedroom/8.5 Bathroom Large Luxurious H...

This roomy 4th row Palmetto Dunes home is the ideal place for a huge family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
Family friendly home with an ocean view ...

Summary:Villamare 1410The Space:Make your next trip to Hilton Head Island an exceptional one by staying in this impressive home in the Palmetto Dunes Resort! Only walking distance to the beach, and with striking vistas of the Atlantic Ocean right...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
This fully renovated Hilton Head Vacatio...

This charmingly remodeled Hilton Head vacation rental offers a extravagant coastal escape. It is located on the 4th floor with elevator access for painless arrival. The roomy living room features a huge mounted flat-screen TV and direct access to a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Updated getaway with pools, hot tub, clo...

Summary:Hilton Head Resort 1424The Space:NOTICE:Feel the best of Hilton Head Island in this refreshed apartment, where you can appreciate the island's pristine beaches, legendary golf courses, and countless sunshine. With cycling paths close by, you...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

First Friday Dinners

Victoria Valley Vineyards at Table Rock

Book online
$65.00 - $75.00

duration: 2.5 Hours group_size: Max 30 People description: Join us for an enchanting evening at our First Friday Dinner from 6 pm to 8:30 pm, as we celebrate friendship and good food in the picturesque setting of Victoria Valley Vineyards. This is...

Three Hour Private Inshore Charter

max_age: 99 group_size: Up to 6 guests description: Spend a day fishing Hilton Head Island waters with Captain John aboard the Sweet Pea, a 29 ft World Cat outfitted with modern electronics, tackle and an enclosed head for comfort. This inshore...

Fishing Charter

Reel Native Fishing Charters

Book online
$350.00 - $1,150.00

description: Let's get out on the water and makes some memories that will last a lifetime! Rates & Duration - 2 Hour Charter • $350 - 3 Hour Charter • $475 - 4 Hour Charter • $575 - 5 Hour Charter • $700 - 6 Hour Charter • $875 - 8...

Private Lesson with Clark Sinclair

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

meeting_point: George Fazio Course description: About Clark Sinclair, Director of Golf Clark Sinclair has been a member of the Palmetto Dunes staff since 1983 and has been teaching since 1986. He is a graduate of Presbyterian College. Clark...

Jet Ski

Lowcountry Watersports

Book online
$159.00

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 description: Experience an exhilarating...

Round Trip To Downtown CHS

Daniel Island Ferry

Book online
$10.00 - $50.00

duration: 30 Minutes cancellation_summary: 48 Hours before departure - refund or credit available. 24-28 hours before departure - credit for a future trip. Inside of 24 hours - no refund or credit. meeting_point: 1 river landing drive, Daniel...

SCM WAHHI Outback Page Island

description: *Boating and kayaking in pristine salt marshes!* --- Description One of our signature programs and an exceptional value from Outside! The Outback begins with a guided boat trip where the captain shares stories of the Lowcountry...

Twilight Guided Ghost Story Tour

Mungeon Creek Golf Cart Rental

Book online
$61.32 - $235.85

duration: 2 Hours group_size: Up to 20 guests description: Ride into the haunted history of Daufuskie Island with our Twilight Guided Ghost Story Tour! Join us for a chilling 2-hour adventure as the sun sets and shadows creep across the island. Your...

Dolphin Nature Cruise

Island Time Charters

Book online
$325.00 - $399.00

Duration 2 or 3 Hour This is our most popular cruise for a reason! About This Dolphin and Nature Cruise takes you on the waters surrounding Hilton Head Island which inhabit hundreds of Atlantic Bottlenose Dolphins along with, osprey, great...

Outside DMC Partner Outing - Palmetto Bluff Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

Exclusive Encounter

Bee City Zoo

Book online
$250.00

description: Duration Best for ages 5 and up!! This 20 min encounter does not include admission and requires an admission ticket for each guest with a maximum limit of 5 guests. About Choose one of the ambassadors below: - Sloth - Capybara ...

Hilton Head, SC

Hilton Head Island is a resort destination on the South Carolina coast known for its pristine beaches, world-class golf courses, and natural Lowcountry beauty.

Located just north of Savannah, Hilton Head combines upscale amenities with a relaxed island atmosphere. The island features 12 miles of wide sandy beaches, extensive bike trails, and a variety of outdoor activities including kayaking, dolphin cruises, and nature tours. Visitors can explore iconic spots like Harbour Town Lighthouse, enjoy local seafood at waterfront restaurants, or spend the day shopping and sightseeing in one of the island's many charming villages.

Hilton Head is home to a wide range of lodging options, including vacation rental homes, oceanfront resorts, and golf villas. The island is perfect for families, couples, and anyone looking for a mix of relaxation and recreation. Whether you're teeing off on a championship course, biking beneath moss-draped oaks, or simply soaking up the sun on the beach, Hilton Head offers a polished and peaceful coastal escape with something for everyone.

Hilton Head Island is arguably one of the most popular beach towns along the southern Carolina coast, with world class resorts and vacation rentals, gorgeous beaches, and plenty of entertainment available both on and off the beach. A regular on national "Top Ten Vacation Destination" lists, the island has an elite resort town feel that can easily cater to a wide range of tastes and interests.

Hilton Head SC

Boating, fishing, golfing, tennis, swimming, shopping, dining, and historical touring are all readily available in this somewhat small isle, and is all located within a 15 or 20 minute drive from any point in town. With luxurious amenities and accommodations, plenty of art and historical attractions, and even its own Symphony Orchestra, Hilton Head Island essentially takes the concept of an elite vacation retreat to an entirely elevated level.

Hilton Head SC

Hilton Head Island is one of the southernmost seaside isles along the South Carolina coastline and is located just a few minutes away from the Georgia state border. Separated from the mainland via the Calibogue Sound, the relatively wide island is a unique mixture of varying coastal landscapes, including ocean and sound facing beaches, with miles of rugged maritime forest in between. Because of this, even the most expansive resorts have a feel of relative privacy about them, as virtually every side street is lined with towering oaks, cedars, pines, and other evergreen foliage. The island is a total of 69 square miles, which includes roughly 28 square miles of water, but feels relatively small, as virtually any point can be easily reached via the William Hilton Parkway which circles through the interior of the island.

Hilton Head SC

Hilton Head has always been a popular destination, it seems, as archeologists have found ancient trash heaps that date back 4,000 to 15,000 years to the island's first native residents. Hilton Head did not garner international attention until 1521, when a Spanish New World exploration landed and began making friendly relations with the local inhabitants. The English Captain William made a more lengthy exploration in 1663, essentially re-discovering the area and its alluring proximity to Port Royal Sound, and naming the area "Hilton Head," after himself.

Hilton Head SC

Over the next several centuries, parcels of the island would be granted or purchased by new North American settlers, and the region would flourish as a site for Sea Island Cotton and Indigo plantations. A small chapel was constructed, the Zion Chapel of Ease, for the convenience of the newly wealthy plantation owners, and hundreds of slaves were brought to the area to tend the expansive farms. When the Civil War began, Union forces, recognizing the prime locale of Hilton Head directly in between the main southern ports of Savannah and Charleston, attacked the area with 12,000 troops, successfully overtaking the region on November 7th, 1861, and maintaining control of the territory for the duration of the war.

Hilton Head SC

Shortly after the battle, the Union forces freed the hundreds of slaves who lived and worked on the island, making them the first slaves that were freed during the war, and the first pioneers of a new, solely freed-slave village called Mitchelville. Four forts were constructed on the island, and while these Union strongholds are long gone, visitors can still visit the discreet remnants of Fort Howell and Fort Mitchel while touring the island.

Hilton Head SC

Life was quiet for the next few decades after the war, until 1931 when a Wall Street Tycoon purchased 17,000 acres of the island as a private gaming reserve. This purchase would prove to be prophetic, as in the decades that followed, the town would grow exponentially to accommodate the growing elite group of guests. This growth arguably didn't really begin until 1956, when the two-lane toll swing bridge, the James F. Byrnes Bridge, was built to allow vehicular traffic to the island for the first time, and a local developer, Charles E. Fraser, began the construction of the Sea Pines Resort.

Today, Hilton Head Island is a sprawling, but never overcrowded, collection of elite resorts, vacation rentals, hotels, and all the standard vacation amenities that an elite destination requires. Best of all, with historic attractions like the Zion Cemetery and Baynard Mausoleum, and the Mitchelville Freedom Park, visitors can always revisit Hilton Head's long and storied past.

Day-trippers will find a number of public accesses to pay a visit to Hilton Head's renowned shorelines, including Folly Field Beach Park, Driessen Beach Park, and Coligny Beach Park. While the beaches certainly claim the lion's share of admiration and attention, Hilton Head Island also has a number of attractions off the shore that will appeal to visitors of all ages.

Kids love exploring the Adventure Cove Family Fun Center and The Sandbox Interactive Children's Museum, while visitors of all ages can easily enjoy the Coastal Discovery Museum, the Baynard Plantation Ruins, and the Harbour Town shopping, dining and water sports complex, which is also home to the famed Hilton Head Lighthouse.

When it comes time to eat, vacationers will find hundreds of options that range from exquisite five star eateries to classic cafes and sandwich shops, and everything in between. Hilton Head Island is especially known for its waterfront dining options, and visitors will find gorgeous sunset-front establishments throughout the region.

There are just as many options when it comes to accommodations, as Hilton Head is home to a wide range of hotels, resorts, and weekly vacation rentals. The hotels and resorts are, for the most part, all-inclusive, with expansive private pools, golf courses, spas, and wide private beaches to entice guests, while the vacation rentals can range from small villas and condos to expansive 6 or 7 bedroom beachside estates. Clearly, every party size and expectation can be easily met, and potential vacationers will have a hard time determining where to stay on the island for a relaxing retreat.

Hilton Head Island has arguably been a popular destination for hundreds and even thousands of years, and it won't take new visitors very long to figure out why. With ample white sand beaches, cool shopping options, exceptional restaurants, and a world of attractions around every shaded street corner, it's easy to enjoy an activity-packed but incredibly fun and relaxing vacation. A favorite destination along South Carolina, Hilton Head continues to maintain its longstanding reputation as one of Coastal Carolina's most accommodating and luxurious retreats.

Hilton Head Vacation Guides