Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Large Updated Three-Bedroom Condominium ...

This enormous three-bedroom Hampton Place condominium sits oceanfront and has been wonderfully refreshed.Indulge in the ultimate beach vacation at this handsome 3-bedroom oceanfront getaway. Located on the charming first floor, this condo offers...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
New to the Rental Market!

This well maintained three bedroom, one level home in the heart of Palmetto Dunes has it all! It is located just a short walk to both the beach and the George Fazio Golf Course!Upon entering the home, there is an open office space with a murphy bed...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Sunny & bright, dog-friendly condo w/ go...

Inverness 942Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Inverness Village, a complex located near golf courses, beaches, and so much more...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
104 Barrington Arms 3 Bedroom 3 Bath

Welcome to this gorgeous three bedroom oceanfront condominium, ideal for families seeking a opulent and cavernous hideaway. This huge condo offers comfort, style, and charming ocean vistas.The completely equipped kitchen features sleek granite...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Stunning Oceanfront View! Heated Pool
4.6
(12)

Ocean Dunes 320: A Premier Oceanfront Getaway!!Discover the appeal of Ocean Dunes 320, a elegantly designed oceanfront villa that combines modern comfort with striking Atlantic vistas. This inviting getaway offers all the amenities of home...

  • Hilton Head
  • 1 Bedrooms
  • 1 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 handsome 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

Hilton Head Tours & Activities

Afternoon Half Day Sail Trip On Seas the Moment - Our Newest Boat
Book online
$1,156.40 - $1,350.00

duration: 4 Hour description: Set Sail for a half day adventure aboard our Monohull Sailboat. This trip is customizable for you and your group. Sail out to the Ocean and do some ocean sailing (providing conditions allow) or anchor and enjoy some...

Taste of Charleston

Unwritten Charters LLC

Book online
$600.00 - $900.00

Beat the heat and enjoy a Beautiful Morning Cruise, We can explore the waterways and Islands around Charleston in the cool of the day! Duration 2 or 3 Hours About A great time to see the harbor. See USS Yorktown, Ravenel Bridge, Battery Park...

One Day Beach Cornhole

Hilton Head Outfitters - Bike Rental

Book online
$45.00

PORTABLE CORNHOLE SET – This tailgating game includes 2 portable cornhole boards (2x3 feet), 8 all-weather regulation bean bags, and cornhole Rules. For travel, tailgating, beach, lawn, or backyard WATER FILLED - Lightweight travel cornhole boards...

2 Hour Private Afternoon Sail and Dolphin watch on Knot The Office

*Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with handling sails if you desire, but either way, kick back...

Morning Segway and Coffee
Book online
$115.00

Start your day on a caffeinated Segway ride! Duration 1.5 Hours About 50% Segway. 50% Coffee. 100% Fun! Join us for this fun & unique way to explore Hilton Head Island! This 2.5 hour tour will be one of the highlights of your vacation...

May River Ecology Excursion

May River Excursions

Book online
$40.00 - $50.00

*Learn about the ecosystem and wildlife of the May River!* ___________________________________ Rates **Adult** - $45.00 **Child** - $35.00 **3 Adult minimum to go out** ___________________________________ Duration 1.5...

Beaufort Lands End Paddling

Book online
$40.00 - $60.00

duration: 1.5-2 hours meeting_point: Russ Point Boat Landing, Sea Island Pkwy & Fripp Island Bridge (across from Nature Center) description: Join us for a one-of-a-kind kayak adventure, perfectly timed with the high-tide, offering exclusive access...

Shared / Sunset Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$59.75

duration: 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

Ten Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$78.60 - $187.10

Enjoy miles and miles of scenic bike paths Duration 10 Days About Free locks with all rentals. Baskets and helmets also available - please select during check-out! More info Free locks with all rentals - please select during...

Private Disappearing Island Dolphin Tour
Book online
$379.00

duration: 2 Hours • All Ages cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 group_size: Maximum 6...

Playing Lesson

Palmetto Dunes Golf Academy

Duration & Rates - 2 hours - Price varies. Please call to get pricing. About Play with the Pro & learn as you go. Videos, photos & instruction notes are included. - When: Seasonal - by appointment only & course availability - Where: TBD - Ages...

Exclusive Encounter

Bee City Zoo

Book online
$250.00 - $275.00

Duration 20 min encounter About Choose one of the ambassadors below: - Sloth - Capybara This encounter will include a photo with your ambassador, however no admission tickets are included with this encounter. Admission tickets to be purchased...

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