Hilton Head, SC Vacations

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Featured Vacation Rentals

Stunning Condo in Plantation Club with V...

Vista Verde - Vacation Units by Five Star Properties“Vista Verde”….Green sprawling vistas abound as soon as you take your first step into this 2-bedroom 2-bath upgraded Hilton Head condo rental at Plantation Club villa. All this, just a short...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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
Beachfront condo with large furnished ba...

Summary:Beachside Tennis 1893The Space:Appreciate vistas of the ocean and Calibogue Sound from this bright and welcoming condo. While the highlight of this rental is surely the furnished wraparound balcony, there's plenty inside to make you happy as...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Waterfront Penthouse Villa with Shared P...

Sea Cloisters 512Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stay in the fifth-floor penthouse villa of this oceanfront complex on Hilton Head Island, SC...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Charming, family friendly condo with pri...

Summary:Turnberry Village 251The Space:Sunkissed skin and salty air await you at this Hilton Head Island getaway. Sporting a full kitchen with modern appliances, a enormous living area with a flat-screen TV, and a private deck surrounded by...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Hilton Head Stay | Beach, Pool + Full Ki...

The Village at Palmetto Dunes offers a casual Hilton Head stay just steps from the beach, with simple access to golf, tennis, pickleball, and spectacular bicycle paths. Located within Palmetto Dunes Resort, this property places you close to Shelter...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Private Sunset & Fireworks Cruise - 16p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Little Swingers

Palmetto Dunes Golf Academy

Book online
$50.00

meeting_point: Robert Trent Jones golf course min_age: 3 max_age: 7 description: Duration & Rates - 50 minutes - $50 per student Little Swingers (offered seasonally) Sundays 10AM - 10:50AM Tuesdays 2:00PM - 2:50PM June1st-August 31st Learn...

Self-Guided Tours

Historic Mitchelville Freedom Park

duration: 6 Hours description: Discover the rich history of Mitchelville at your own pace with our Self-Guided Tours at Historic Mitchelville Freedom Park This flexible tour option allows you to explore the birthplace of freedom for formerly...

Eight Day Bike Rental

Wheelz of Hilton Head

Book online
$55.00 - $110.00

description: Eight Day Bike Rental Rates Duration 8 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Independence Day Float-a-Palooza

Saluda Lake Landing

Book online
$5.00 - $20.00

duration: 12pm-6pm max_age: 101 group_size: 300 description: Independence Day Float-a-Palooza Celebrate Independence Day weekend on the water at Saluda Lake Landing! Join us July 3rd, 4th, and 5th from 12 PM–6 PM for three days of floating...

3-Hour Adventure Cruise

Hilton Head Boat Charters

Book online
$495.00 - $995.00

duration: 3 Hours cancellation_summary: We need at least 72 hours' notice for a full refund. meeting_point: 43 Jenkins Island Rd, Hilton Head Island, SC 29926 group_size: Up to 20 People description: This is your "Best of the Low Country" day on the...

PB 2 Hour May River Kayak Nature & History Paddle

meeting_point: Palmetto Bluff, Bluffton description: On this casual tour, you'll explore the local creeks with a naturalist guide. No kayak experience is necessary. Duration 2 hours Meeting Location - This activity will meet at the Paddle...

Boomerang Private Charter Fishing
Book online
$540.00 - $640.00

meeting_point: Palmetto Bay Marina description: Rate **Three Hour** - $540 **Four Hour** - $630 About The Boomerang 2 is a comfortable 28 foot Parker center console that is powered by two brand new Suzuki outboards. We specialize in fun...

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 Days meeting_point: Hilton Head Island, SC description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day...

Thirteen Day Electric Bike Rental

duration: 13 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...

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

Lowcountry Curated: Hilton Head E-bike and Picnic

duration: 4 Hours meeting_point: 50 Shelter Cove Lane, Hilton Head, SC 29928 min_age: 16 group_size: 4/10 pricing: $198 description: Explore Hilton Head’s storied past on a guided e-bike tour to Mitchelville, the nation’s first freedmen’s...

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