Hilton Head, SC Vacations

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Featured Vacation Rentals

Lofted villa with private deck, streamin...

Summary:Sealoft 2055The Space:A lofted villa in a canopy of trees where the windows are the walls is waiting to welcome you to sun-soaked, oceanside, Lowcountry living! This unique, treehouse-like getaway offers a convenient location just a short...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
First Floor - Two Bedroom Golf - Course ...

In 1986 my family and I visited Hilton Head for the first time. In 2012 we realized our dream and purchased Evian 228. Since then we have done major renovations including all new floor and a new coat of paint in the summer of 2023. Previously we...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Expansive Views of the Pool, Lagoon and ...

Located on the 3rd floor, this gorgeously modernized two-bedroom, two-bath villa offers gorgeous vistas of the community pool and the Atlantic Ocean. Ideal for a calming hideaway, it’s appealingly located within the Barrington community. It...

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

Summary:Moonshell 31The Space:The ideal Hilton Head vacation awaits at this sizable, elegantly furnished vacation home, which features a fireplace, screened-in deck, and handsome private pool! For a modest nightly fee, your canine family members are...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 13
Stylish Home with Private Deck, Shared P...

Summary:Queens Grant 621The Space:Queens Grant 621 is a freshly-remodeled, family-friendly condo offering roomy living areas that everybody can savor. Interior renovations include new furnishings throughout and an refreshed, well-equipped kitchen...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 9
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 sizable living area with a flat-screen TV, and a private deck surrounded by greenery...

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

Hilton Head Tours & Activities

Dolphins, Sharks & Shells!

Dolphin Discoveries Hilton Head

Book online
$475.00 - $845.00

duration: 3 to 6 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Three Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$15.00 - $60.00

duration: 3 day bike rentals cancellation_summary: NO REFUNDS OR RAINCHECKS meeting_point: your address description: Bike rentals for a three day period. (Example: you rent the bikes on monday, they are due back thursday morning) what_is_included...

HHI: Tales Through Time

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about island history from an expert!* ___________________________________ Duration 1 Hour ___________________________________ About Hilton Head Island has been visited and inhabited for over 4,000 years—from the...

Glow With the Flow Fridays

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Light up your weekend! Glide down the river with glowing gear, good vibes, and nonstop Friday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with friends, and soak in the magic of the...

Romantic Sunset Cruise

Island Time Charters

Book online
$399.00

The most spectacular views and vivid colors! Duration 2 Hours About Come aboard for an enchanted, romantic cruise! Bring your favorite bottle of bubbly and we will provide the rest. This charter includes a sweet treat, fresh flowers, and...

Genesis Compound Rental & Range Time

duration: 1 Hour Range Time description: Curious about archery but don’t own equipment? Our Genesis Compound Tryout Experience includes everything you need — bow, arrows, and range time — with guidance from our knowledgeable staff. It’s the...

Afternoon Half Day Sail Trip On Seas the Moment - Our Newest Boat
Book online
$1,203.60 - $1,450.00

duration: 4 Hour cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

Blue Crab Discovery

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $90.00

duration: 1.50 description: *Explore where Atlantic Blue Crabs live, how they impact local communities, and why the Lowcountry enjoys and protects this food source!* ___________________________________ Duration 1.5...

Daufuskie Island History & Artisans Excursion

meeting_point: Hilton Head Island, SC description: *Catch a glimpse into Lowcountry history!* --- Description This 4.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of...

Six Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$800.00

description: Duration 6 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, Cobia, Sharks! 6hrs gives us time to target a couple different species, more fishing time...

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...

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head family...

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