Hilton Head, SC Vacations

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Featured Vacation Rentals

300 steps to the beach! - Pet Friendly R...

Located in the very charming Forest Beach, this home features 2 Master Bed Rooms en suite and 2 additional bedrooms with a shared hall bath. Just a short walk to eateries and shopping of Coligny Circle. Freshly redecorated and furnished with a...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Total renovation June 2024, views, pool,...

Anchorage 7473Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This condo is located harborside in the fashionable Anchorage Villas. Spend blue-sky days at the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Dog-friendly house with private pool & l...

BoardwalkOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sit back and bask in the sun and nature of your own getaway with this three-bedroom property...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Large Two Bedroom Villa Located Steps Fr...

Treat yourself to this delightfully appointed, roomy two-bedroom, three-bathroom end-unit villa, located just steps from the pool in the Water Oak community of Palmetto Dunes. As an end unit, the villa enjoys additional natural light, creating a...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Sunset Rentals | Turnberry 212

Palmetto Dunes Resort on Hilton Head is a great vacation destination and your island stay will be even more delightful in this 2 bedroom & 2 bath Turnberry Village townhouse villa with a comfortable bungalow motif. At ground level the front door...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Spacious house by the beach with screene...

Salt Air Sanctuary - 3 Bradley Beach RdOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just a fast walk down the street to Driessen Beach Park, this...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

DI 4 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 Carolina. We...

Day with a Native - Kahuna

Native Son Adventures

Book online
$365.00 - $1,260.00

duration: 3 to 8 hours group_size: Maximum 6 People description: Create a personalized day on the water or choose from favorite itineraries that focus on shark-tooth and fossil hunting, crabbing, fishing, dolphin encounters, birdwatching...

Private Sunset & Fireworks Cruise - 6p

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...

PB 5 Hour Ultimate Lowcountry Day
Book online
$87.50 - $1,175.00

meeting_point: Palmetto Bluff 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 Carolina. We will give...

One Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$39.99 - $129.99

description: One Week Rental Rates: - 16” Kids Beach Bike: $64.99 - 20” Kids Beach Bike $64.99 - 24” Youth Beach Bike: $64.99 - 26” Bike w/ Child Seat: $79.99 - 26” Mens Beach Bike: $64.99 - 26” Unisex Beach Bike: $64.99 - 12" Balance...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Lowcountry Curated: Haig Point Golf Experience

meeting_point: 1 Shelter Cove Lane, Hilton Head, SC 29928 group_size: 4/4 pricing: $795/per person description: Accessible only by boat, Haig Point on Daufuskie Island offers an exclusive golf experience on one of the country’s most celebrated...

Curator's Tour

Coastal Discovery Museum Hilton Head

description: Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg and...

Marsh Madness

Port Royal Sound Foundation

Book online
$60.00

duration: 3-6 pm meeting_point: 310 Okatie Highway min_age: 21 group_size: 200 accessibility: Wheelchair accessible description: PRSF fundraiser for research & conservation efforts focused in the Port Royal Sound area. Enjoy an oyster roast, BBQ...

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...

Public Sailboat Charter

Charleston Sailboat Charters

Book online
$125.00 - $1,599.00

Duration 2.5 Hours About After a brief safety speech, we will shove off the dock and head into the scenic Charleston Harbor. As we raise the sails and turn the engine off, you'll immediately feel the relaxation set in and discover why the...

Savannah Wildlife Refuge Hike

Hilton Head Island Recreation Association

Book online
$30.00

duration: 3hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Up to 14 people description: Hosted by Moore 2Life. Come explore the Savannah Wildlife Refuge from the comfort and warmth of the Island...

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