Hilton Head, SC Vacations

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Featured Vacation Rentals

SeaPines, Updated, Golf view, On site po...

This centrally located Plantation Club three bedroom villa is a short walk to the gorgeous SeaPines Beach Club and Golf Clubhouse. Stunning updates in 2022 include new carpeting, furnishings, sliding glass doors, screened porch refurbishment and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Palmetto Dunes - 713 Barrington Drive - ...

Appreciate a calming stay in this gorgeously remodeled 1-bedroom villa with a king bed at Palmetto Dunes Beachfront Resort, steps from pristine beaches and within reach of top golf courses, tennis courts, and bicycle trails.Breathe in the salty air...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Mid-Island Retreat | 2 Pools, Hot Tub, 1...

Fiddlers Cove 19KOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the gated Fiddler's Cove community, this 2BR/2BA condo offers a calming top-floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Coco Cabana - Indoor & Outdoor Pools @ H...

Welcome to COCO CABANA, a gorgeous and freshly designed Vacation Ready Services condo located at Hilton Head Resort! Located on the 4th floor of Building #1, this striking two bed & two bath island hideaway is the ideal getaway for families and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 9
Delightful Condo W/ Beach Access, Shared...

Breakers 305Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bright and filled with beachy vibes, this Hilton Head condo will be the ideal jumping-off point...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Centrally located in Hickory Cove with s...

Welcome to your ideal Hilton Head hideaway in the esteemed Palmetto Dunes Resort! Located in the serene Hickory Cove section, this 2-bedroom, 3-bath villa offers gorgeous vistas of the relaxing 11-mile lagoon and the ideal setting for a memorable...

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

Hilton Head Tours & Activities

Eight Day Electric Bike Rental

duration: 8 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time Each Way cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Hilton Head -> Daufuskie Island...

Costume of The Living Dead Paddle

Saluda Lake Landing

Book online
$8.00 - $40.00

duration: 2hr min_age: 1 max_age: 101 group_size: 50 description: Get ready to rise from the lake as the undead! Paddle of the Living Dead is a glow-in-the-dark costume paddle where zombies, witches, pirates, and creatures of the night cruise across...

Valentines Nature Art for Seniors

Hilton Head Island Recreation Association

Book online
$25.00

duration: 1.5hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Maximum 20 people description: Come join Moore To Life and Island Rec Center for a holiday craft day. Give the gift of nature. Whether...

24  Hour E-Bike Rental(Pick-up/Return between 9 and 4:30)

duration: 24 Hours meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get...

Marsh Critters

Coastal Discovery Museum Hilton Head

Book online
$10.00

description: *Learn about the creatures of the salt marsh ! Great for families with younger children.* ___________________________________ Rates - **$10 per person aged 3 and up, under 3 Free** ___________________________________ ...

Sport Crabbing Adventure
Book online
$10.00 - $1,000.00

description: Join us for a Sport Crabbing Adventure! Duration 1 hour 45 minutes Tour About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on vacation! Well …...

DI 6 Hour Ultimate Lowcountry Day

meeting_point: Daufuskie Island, SC description: *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 South...

Marriott Vacation Club Daufuskie Tour

meeting_point: Hilton Head Island, SC description: Tucked between Hilton Head and Savannah, and only accessible by boat, Daufuskie is a must-see in the Lowcountry!

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.

Dolphins & Donuts

Lowcountry Watersports

Book online
$10.00 - $49.99

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours before the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 max_age: 99 group_size: 48 accessibility: Ramp...

Daufuskie Island History and Artisans Excursion

Coastal Discovery Museum Hilton Head

Book online
$75.00 - $115.00

meeting_point: Shelter Cove Marina description: *Boat cruise from Hilton Head to Daufuskie Island* ___________________________________ Duration 4.5 Hours ___________________________________ About Tucked between Hilton Head Island and Savannah...

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