Hilton Head, SC Vacations

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Featured Vacation Rentals

Welcoming villa with shared pool, nearby...

Summary:Island House 138The Space:Escape to the enchanting appeal of Hilton Head Island, where white sandy beaches and acclaimed golf courses set the scene for an memorable hideaway. Ideally located, this enchanting villa places you within simple...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Ocean view condo with shared pool steps ...

Summary:Captains Walk 448The Space:Make your next vacation one to remember in this inviting island home just steps from the sand. There is nothing better than stepping out to the balcony and feeling the sea breeze in your hair and the sun on your...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Unique Treehouse Haven with Marsh-Front ...

Summary:Sealoft 2042The Space:Appreciate lush surroundings in a handsome treehouse that offers all of the amenities of modern life along with close by fishing areas, beaches, rivers, and the ocean. You'll be well-served by this Sea Pines treehouse...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beautiful Beachside Resort-Indoor/Outdoo...

SUN, SAND, TENNIS AND GOLF!!Just what a dream vacation is made of!! Come join us at our Hilton Head villa for an memorable vacation...Unit is in Bldg. 3 (2nd floor) includes 2 bedrooms with TVs, living room with sizable TV, entirely outfitted...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 7
Island Resort Getaway  3 Pools, Hot Tub,...

Summary:Hilton Head Resort 4222The Space:NOTICE: Boasting a plethora of on-site amenities, your ideal family beach vacation awaits at this choice 2BR/2BA Hilton Head Resort condo. Perks include a completely equipped kitchen, coastal chic decor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beautifully renovated 1 bedroom villa wi...

Summary:HH Beach & Tennis 344BThe Space:This gorgeously refreshed, 1 bedroom, 1 bathroom condo features gorgeous ocean vistas. Wood floor spans the property with tile floor in the freshly remodeled bathroom. The living area is comfortably furnished...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

PB Private Kayak Tours & Instruction

meeting_point: Palmetto Bluff description: *Get on the water with one of our custom kayak tours & classes* About If you can dream it, we can do it! Outside Palmetto Bluff private kayak tours and instruction programs are designed around your...

Six Hour Private Offshore Charter
Book online
$1,200.00

max_age: 99 group_size: For up to 6 guests description: Head out from Hilton Head Island for a private fishing charter aboard the Sweet Pea, a 29ft World Cat equipped with modern electronics and tackle. Captain John, a certified and experienced...

Limited Edition T-Shirts

Historic Mitchelville Freedom Park

Book online
$15.00

pricing: $15 description: Juneteenth Limited Edition T-Shirts

Private Offshore Fishing Charter
Book online
$1,200.00 - $1,600.00

description: Fish like a local! Duration 8-10 Hours About The 8 hour trip allows up to get up to 20 miles offshore fishing artificial reefs and wrecks, weather permitting. Main target are cobia, bull reds grouper, king mackerel, sea bass, and...

Private Charter (up to 14 passengers)

Island Head- Hilton Head Harbor

Book online
$229.00 - $1,374.00

Three Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Fishing Charter - The Native

Native Son Adventures 2

Book online
$365.00 - $1,260.00

duration: 3 to 8 hours meeting_point: C.C. Haigh, Junior. Landing, Hilton Head Island , SC 29926 description: Spend a day on a stable, shaded fishing boat designed for comfort and big catches. Whether you choose a shorter near-shore trip or a longer...

Private Lesson with Jason Heintenchel

Palmetto Dunes Golf Academy

Book online
$90.00

meeting_point: Arthur Hills Golf Course description: About the Palmetto Dunes Golf Academy The Palmetto Dunes Golf Academy in Hilton Head, South Carolina, is one of the most respected golf schools in the world. Featuring lessons, clinics and...

A.C.E. Basin & Monkey Island Tour

Beaufort Dolphin Adventures

Book online
$372.64

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

Intro to Wheel-Throwing | Pottery Wheel Basics

meeting_point: Mayfair Art Studios- 1885 Hayne St. Spartanburg, SC 29301

Private Inshore Charter Fishing aboard Hobo

duration: 3 hours cancellation_summary: 48 hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way. Please proceed down to the first dosk on the right side of the marina. group_size: Licensed for up to 16 passengers; rate includes 6...

Banana Boat Rides

H2O Sports

Book online
$39.00

duration: 20 Minutes min_age: 6 description: Come enjoy an exhilarating ride aboard the 6 passenger, double-sided banana boat. Duration 20 Minutes About The journey begins in Harbour Town as you load up on the banana boat and steady yourself...

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