Hilton Head, SC Vacations

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Featured Vacation Rentals

Sunset Rentals | Beachwalk 165 | Dog Fri...

A completely modernized first floor and simple access to many amenities await you in this immaculate, pet-friendly villa tucked in a peaceful corner of Beachwalk Villas in Shipyard Plantation, Hilton Head Island. As you enter, you are welcomed into...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Brand New LUX Townhome-Mins to Beaches, ...

Feel Coastal Luxury at 180 Olive Shell Court – Your Hilton Head Island RetreatWelcome to your dream vacation hideaway on striking Hilton Head Island – consistently ranked the #1 island in the U.S. by Travel + Leisure readers for its pristine...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
2 Bedroom updated condo

Welcome to your ideal Hilton Head Island hideaway! This attractively decorated 2 bedroom 3 bathroom condo with a loft offers a peaceful escape overlooking the esteemed Robert Trent Jones Golf Course. With designer touches throughout and...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Family-friendly condo with washer/dryer,...

Village House 106Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Village House 106 is a handsome two-bedroom, two-bathroom villa so close to the beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
HEATED OUTDOOR & INDOOR POOL! Monthly Ra...

Welcome to your dream hideaway at OCEAN LINKS - a impressive and freshly designed Vacation Ready Services condo located at Hilton Head Resort! Located on the 3rd floor of Building #2, this calming two bed & two bath island hideaway is the ideal...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Brand new coastal renovated beach villa ...

Brand new coastal modernized beach villa just steps from beach and pool. With quartz counters, new white shaker cabinets, designer tile walk-in shower, striking ocean vistas. Everything has been refreshed! Ideal for a family up to 6 people.Pack...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

3 Hour Private Spring Jocassee Boat Tour

Private 3hr Spring Tour on Beautiful Lake Jocassee! Rates - Private Charter (includes up to 6 people): $350 ***$50 for each additional person (up to 10 total passengers)*** About Boat Tour includes all major waterfalls, Limited swim time...

Yellow Moke Rental At Old Town Bluffton Inn
Book online
$300.00 - $1,450.00

The best way to travel around Hilton Head! Duration Daily & Multi-Day Rentals About Leave your family car behind and rent a Moke for the day, weekend, or your entire vacation! Experience the open air while shopping, visiting friends or just...

Adopt-a-Dolphin

Coastal Discovery Museum

Book online
$50.00 - $100.00

About Sixty percent of all adoption money goes directly to the scientists who are studying these magnificent mammals and helps fund interns studying these dolphins, boat fuel, and supplies needed for the Marine Sensory and Neurobiology Lab in...

Palmetto Dunes Lagoon Charter

Palmetto Lagoon Charters

Book online
$410.00 - $610.00

Try some of the best fishing on Hilton Head Island - all while in the flat, calm waters of the Palmetto Dunes Resort lagoon system. A nursery to a variety of saltwater fish species, this lagoon system holds giant redfish, trout, bluefish, black...

Tuesday night Firework Sailings

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

About Night time Fire Work sailing charter! More info **Pricing:** • 1-6 people: $600.00 and $100 for each additional person up to 14. ($1,400) • 15-20 people is a flat $1,500.00

Explore Honey Horn

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

*Learn about Honey Horn's past and natural history!* ___________________________________ Duration 1 Hour and 30 Minutes ___________________________________ About Begin your Honey Horn experience with this guided tour around the museum’s...

Bunny Eggspress

The South Carolina Railroad Museum

Book online
$17.00 - $140.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Easter each year. Riders will board the train for a 3-mile trip to the Pumpkin Patch. We will stop the...

Carmines Family Climb with Seafood Fest

Hilton Head Island Recreation Association

Book online
$5.00 - $20.00

duration: 1-3 Hours cancellation_summary: Cancellation Policy: To be eligible for a full refund, all cancellations must be made up to 24 hours before the scheduled start time. We can also move you to another session time if spots are...

Private Fireworks Cruise

Hilton Head Yacht Charter Company

Take to the water in style! Rates $5,000 for a private charter, up to 12 people Duration 4 hours About Hilton Head Yacht Charter at night is all about you. Imagine a luxury yacht, designed for ultimate entertainment, slipping through the...

Three Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$485.00 - $740.00

Golf Cart Rentals! Duration 3 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online due to South...

Old Town Bluffton Inn May River Discovery Cruise

duration: 90 Minutes meeting_point: 110 Calhoun Street, Calhoun Street Dock group_size: Maximum 6 people pricing: . description: Take a cruise on the May River in an authentic South Carolina skiff boat. Your guide is a master captain and an expert...

Pontoon Boat Rental

Island Head- Hilton Head Harbor

Book online
$275.00 - $2,200.00

*Explore the Low Country on your own!* ___________________________________ Rates and Duration **Two-Hour Rental:** $275 **Three-Hour Rental:** $375 **Four-Hour Rental:** $475 **Five-Hour Rental:** $549 **Six-Hour Rental:** $649 **Seven-Hour...

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