Hilton Head, SC Vacations

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Featured Vacation Rentals

3rd-floor condo with balcony, lagoon vie...

Summary:Island Club 6302The Space:When you book this third-floor condo you will get the best South Carolina experience ever! This family-friendly condo overlooks a beautiful lagoon from a private balcony, which is also furnished with a modest bistro...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's palmetto and oak trees. Walking paths and boardwalks give you fast and simple access to the community's beach area.After...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Sunset Rentals | Kingston Dunes 58 | Dog...

The ideal Hilton Head vacation starts with finding the ideal Hilton Head vacation rental! Consider it done when you book this 4 bedroom, 4 bath bright and sunny home, located in Hilton Head Island’s Shipyard less than a mile from the beach.To the...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Spacious Home with Private Pool, Game Ro...

Summary:Grandiose TimesThe Space:Book your next family reunion or group vacation at Grand Times, a five-bedroom home with a private pool and terrific location near the beach and multiple golf courses.This home has consistently received 5-star...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
8138 Wendover Dunes- Large Updated Villa...

Welcome to your ideal vacation hideaway! This immaculate three-bedroom, three-bathroom villa is just a short walk from the beach and offers comfort, style, and convenience. With impeccable attention to detail throughout, you'll be thrilled with...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
3rd row home located in the heart of Sea...

HILTON HEAD ISLAND. This roomy 3rd row home is located in the heart of Sea Pines, and is close to South Beach Marina and many island activities. The warm living room features a sectional couch, TV and decorative fireplace and a bathroom off the...

  • Hilton Head
  • 4 Bedrooms
  • 5 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

SCM Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Set sail for an unforgettable evening on the water with Outside Hilton Head’s Lowcountry Boil Dinner Cruise...

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

Three Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$660.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Old T-Shirt

Historic Mitchelville Freedom Park

Book online
$5.00

pricing: $5 description: Old T-Shirt

Private Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00 - $350.00

duration: 1.75 - 4 Hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from...

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$55.00

duration: 30 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: $55 per person for Glow in the Dark Splatter Session. description: It’s your invite to light up the night...

Creek Cat Tour

Lowcountry Watersports

Book online
$120.00 - $145.00

duration: 2 Hours 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 min_age: 5 group_size: 2 people per creek...

Nearshore Fishing Charter

Gone Fishing HHI

Book online
$600.00 - $700.00

description: Fish like a local! Duration 4-5 Hours About Our four hour trip, weather permitting, allows us to fish our inshore creeks, or nearshore wrecks and jetties. Common targets are Red Drum, Black Drum, Trout, Flounder, Sheepshead, and...

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Hibachi Dinner Cruise Experience an...

Forts of Port Royal

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about the battle of Port Royal!* ___________________________________ Duration 1.5 Hours ___________________________________ About Join a knowledgeable museum docent for an in-depth walking tour of the defenses...

Three Hour Beach Combing and Dolphin Nature Watch Tour
Book online
$375.00 - $415.00

description: *Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

SCM Lowcountry Shrimping Excursion

description: ___ Description Fall in the Lowcountry is shrimp season. Come and join us for what the locals consider a true right of passage. Learn how to throw a cast net for shrimp the way local watermen have for generations. On this 3-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