Hilton Head, SC Vacations

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Featured Vacation Rentals

Ideally located island gem with an outdo...

Summary:Springwood Villas 93The Space:Ideal for a calming hideaway to Hilton Head Island, this two-story condo has all of the amenities of home in a serene package that is sure to spoil you and your guests. The complex is within walking distance to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
4 BR Home, Private Pool, and Spa on Tran...

Appreciate striking lagoon vistas from your own private pool and spa or walk to the ocean in less than ten mins.. Located among live oak trees draped with Spanish moss, and overlooking a lush landscape, this private getaway is the ideal place for...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Large Golf Course View Home with Large P...

This pretty home features opulent wide plank, hand-scraped, black walnut floor throughout the main living areas. This marvelous home consists of six bedrooms, six and a half bathrooms along with an splendid sunroom along with a enchanting nook...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
5 Bedroom Near Ocean Home

Tucked away just four rows from the ocean and directly across from a beach access path, this roomy 5 bedroom, 4 bathroom home offers the ideal blend of comfort, privacy, and unbeatable location.As you enter, you’re greeted by an open floor plan...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Beachfront home with private pool, expan...

Summary:Dunes HouseThe Space:Appreciate life at the beach at Dunes House! This home has impressive vistas of the beach and the Atlantic Ocean. The open living space on the second floor has living, dining, and a well-equipped kitchen that all look...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Two Bedroom Second Floor Condominium wit...

Come appreciate this gorgeous two bedroom ocean view and pool view condominium located within the Villamare community at Palmetto Dunes Oceanfront Resort! The unit has been very well-kept and has elegant room separation, which makes it great for...

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

Hilton Head Tours & Activities

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$80.99 - $161.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Life Under the Sea

Coastal Discovery Museum Hilton Head

Book online
$5.00

description: There is a magical world full of fascinating creatures under the sea! Join knowledgeable Museum staff and volunteers in the Discovery Lab to explore, touch, create, play, and learn more about ocean life. Who lives in those shells? What...

Three Hour Private Inshore Charter

max_age: 99 group_size: Up to 6 guests description: Spend a day fishing Hilton Head Island waters with Captain John aboard the Sweet Pea, a 29 ft World Cat outfitted with modern electronics, tackle and an enclosed head for comfort. This inshore...

Charleston, SC to Jersey City

The Bluewater Academy

Book online
$5,250.00

duration: 7 days meeting_point: 3190 Suite C Matecumbe Key Rd, Punta Gorda, FL 33955 description: The Northern Corridor: A Masterclass in Endurance and Extended Passage making Charleston, South Carolina to Jersey City, New Jersey | June 7th...

Private Lesson with Dustin Hayes

Palmetto Dunes Golf Academy

Book online
$90.00

description: About Dustin Hayes - Dustin has a friendly and fun personality - Trained by the award-winning Palmetto Dunes Golf Academy Staff - Excellent with juniors and adults - Ohio All State Champion About the Palmetto Dunes Golf...

Fishing Charter

Reel Native Fishing Charters

Book online
$350.00 - $1,150.00

description: Let's get out on the water and makes some memories that will last a lifetime! Rates & Duration - 2 Hour Charter • $350 - 3 Hour Charter • $475 - 4 Hour Charter • $575 - 5 Hour Charter • $700 - 6 Hour Charter • $875 - 8...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

Twelve Day Bike Rental

Wheelz of Hilton Head

Book online
$75.00 - $150.00

description: Twelve Day Bike Rental Rates Duration 12 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...

Family Archery Outing with Range Time

duration: 1 Hour Range Time group_size: Up to 2 Adults & 3 Children (under 16 Years old) description: Bring the whole family together for a fun and memorable activity everyone can enjoy. Our family package includes equipment rental and range time...

Shelling, Shark Tooth, & Dolphin Excursion
Book online
$45.00 - $525.00

description: ___________________________________ Rates are based on 6ppl **2 Hours** - $300.00 **3 Hours** - $400.00 **4 Hours** - $475.00 *Can take a maximum of 12 people. Each additional person is $35* ___________________________________ ...

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...

Junior Clinics

Palmetto Dunes Golf Academy

Book online
$50.00

duration: 50 minutes min_age: 8 max_age: 17 description: Duration & Rates - 50 minutes - $50 per student - Sundays at 11AM and Tuesdays at 1:00PM June1st-August 31st Junior Clinics - "Fun, Friends and Fresh Air" (offered seasonally) Enjoy...

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