Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Beach Villa - Close to all the action! B...

New kitchen complete with granite countertops. Freshly painted and new floor throughout.Bedroom 1 - Queen Bed with complete bath, Bedroom 2 - twin over full bunk beds with complete bath. Villa has laundry facilities, outdoor patio with a grille and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Well Updated with Beach Contemporary Dec...

This refreshed, pretty two bedroom, two bath villa is located directly beside the Robert Trent Jones Driving Range and Clubhouse and is also just steps to the pool! You will feel instantly on vacation as you enter this coastal villa! The warm and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Premium Condo, 3BR, 2BA - Great Amenitie...

AVAILABLE AUG. 18-25, 2023Clean, family-friendly accommodations on one of the best islands in the Southeast. Feel at home with all of the amenities you need inside the condo. Savor all of the phenomenal conveniences outside, including the...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Southern Condo with on-site pools, tenni...

Spa On Port Royal Sound 3337Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to The Spa On Port Royal Sound, a hidden treasure located in the serene...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Cozy condo with pools, hot tub, tennis, ...

Hilton Head Resort 2111Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Leave your worries behind and escape to heaven at this marvelous and welcoming Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beach-view 4th-floor condo with balcony,...

Sea Cloisters 409Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate generous sunshine, sand, and surf for your upcoming hideaway to Hilton Head! This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

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...

What's Wild Family Hike, Pinckney Island

Hilton Head Island Recreation Association

Book online
$5.00 - $45.00

duration: 2hrs meeting_point: Pinckney Island Wildlife Refuge group_size: Up to 20ppl description: Enjoy a Saturday walk with the family on Pinckney Island. An easy and flat 2 mile hike to Wood Ibis Pond and back. Discover the amazing maritime...

Face Painting

Coastal Discovery Museum Hilton Head

Book online
$10.00

duration: 2 meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: Join us for a colorful and creative Face Painting experience! From fierce sharks to magical butterflies, our talented artist will bring Lowcountry critter...

Surf Party

Hilton Head Island Recreation Association

Book online
$40.00 - $500.00

duration: 2 Hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 group_size: 11 description: Let us host your own Surf Party for an unforgettable experience on the beautiful, warm waves of Hilton Head Island...

Flyboard 30 Minute

Carolina Hydrofly

Book online
$129.00

30 Minute Flyboard Pro Series Experience About Each guest will have 20 minutes of flight time and 10 minutes of instruction time. If you would like to book for more than one person, then please process one booking per person by selecting the...

Solaris - Fireworks Cruise (up to 6 passengers)
Book online
$795.00 - $1,000.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book the Hilton Head summer time favorite Fireworks Cruise aboard the all new Solaris! **Our private charters accommodate up to 6 passengers, ensuring an...

Weekend 10:30am-6:15pm Golf Cart Rental
Book online
$70.00 - $90.00

Weekend 10:30 am to 6:15 pm- Golf Cart Rental *Must have valid Driver's License to rent a cart.*

Italian Club - Private Sunset Dinner Cruise

duration: 2 Hours meeting_point: Hilton Head Island min_age: 13 description: Hilton Head Italian Club - Sunset Dinner Cruise! **Book online now for fastest and most convenient check out.** *Departing from Harbour Town!* Duration 2...

Pink Moke Rental

Carolina Rides

Book online
$250.00 - $5,000.00

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...

Palmetto Bluff

Flip Flop Charters

Book online
$625.00 - $750.00

Beautiful Scenery Duration - 3 hours - 4 hours About Nestled on the scenic May River is Palmetto Bluff, an idyllic community on 20,000 acres. Within the community is an extensive nature preserve, private residences, a hotel, several...

Marriott Vacation Club Dolphin Eco

Outside Hilton Head’s Dolphin Eco Tour is one of the most popular tours on Hilton Head Island, providing an unforgettable experience for nature lovers, families, and anyone looking for a fun and educational adventure on the water

Three Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$29.99

Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

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