Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Enjoy 4 rounds of golf per day!!!!!!!

A handsome Labor Day week on sunny Hilton Head Island. Appreciate this stand alone home in a pretty gated community. Beach access, Tennis, 28 rounds of golf for just the cart fee, 2 pools, and hot tub. Book now,

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
3 BR Home with private pool in Palmetto ...

Gone CoastalOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Palmetto Dunes in Hilton Head, SC, this striking home offers the ideal...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Dog-friendly home with private pool, WiF...

Crabline Court 31Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find the ideal group hideaway at this family-friendly beach home, located just a half-mile...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Beach dream w/ balcony view & shared poo...

Windsor Court North 4204Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take a moment and simply relax when you book a stay at this condo by the beach. With...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Bright and spacious home in Sea Pines,  ...

17 Sand Fiddler RdOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal family hideaway in Hilton Head, SC! This immaculate and bright home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Roomy Two-Story Villa with Two Pools - M...

Fazio 11Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to an memorable hideaway when you stay at this enchanting villa on Hilton Head Island...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Three Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miled of bikes paths.

Paws on the Pacolet

Vintage View River Retreat

Book online
$15.00 - $45.00

duration: Hourly meeting_point: 250 Phifer Line Rd, Spartanburg SC 29307 description: Paws on the Pacolet is Vintage View Adventures' dog-friendly kayak experience designed for you and your four-legged best friend! Enjoy a relaxing paddle on the...

Adventure Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 30 Campers description: Experience adventure this summer! Participants will make lasting memories of kayaking, stand up paddle...

Beaufort Waterfront

Flip Flop Charters

Book online
$895.00 - $1,025.00

Explore Calhoun Street! Enjoy a Small Town Atmosphere! - 4 hours - 5 hours About Take a ride across the Port Royal Sound to the second oldest town in South Carolina. Downtown Beaufort is packed with history, art, shopping and dining. Spend...

Ladies Only Clinic

Palmetto Dunes Golf Academy

Book online
$50.00

Learn something new every day! Duration 50 minutes About The Academy presents a daily golf clinic at the Arthur Hills Golf Course, featuring special instruction on the stroke of the day. With a student-instructor ratio of 5:1, you can be sure...

Equestrian Lessons - Montage Guests

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

Sunset Beach Photography

Island Life HH Photography

Book online
$195.00 - $745.00

Capture Sunset Memories To Last A Lifetime Duration Up to 60 minutes, with most shoots lasting about 45 minutes About Want to commemorate a special life moment, celebrate a new addition to your family, or just capture the family fun...

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Fireworks Cruise

BC2 - Island Head

Book online
$89.00

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

4th of July Fireworks Cruise

Drifter Excursions

Book online
$25.00 - $50.00

*Fourth of July – Join us for the spectacular Harbour Town display.* ___________________________________ Rates - **Adults** - $50 - **Kids** - $25 - **Babies** - Free! ___________________________________ About - To view the fireworks...

PB 5 Hour Ultimate Lowcountry Day
Book online
$87.50 - $1,175.00

*Customized adventures are the best way to see and do the Lowcountry!* Description Designed for the family or small group interested in experiencing an authentic day in coastal Carolina. We will give you a menu of options that can include...

Pontoon Rental • 50 Horsepower
Book online
$300.00 - $2,700.00

Full Day Boat Rentals Know Before You Go - All renter's must be 21 years or older. - Can fit up to 7 people. - Full Day Rentals may extend their rental duration at time of checkout. - No pets allowed. - We are unable to provide life jackets for...

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