Hilton Head, SC Vacations

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Featured Vacation Rentals

Luxurious 5th floor One of a Kind Oceanf...

This one of a kind 5th floor penthouse is luxury at its best! It features 3 bedrooms/3 bathroom and spectacular top floor direct oceanfront vistas. The owners have designed and furnished this unit as a home away from home. The expanded kitchen...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Updated, ground-floor island condo with ...

Fiddlers Cove 21BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Island bliss awaits at this ground-floor villa at Fiddler's Cove Beach & Racquet Club...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Second-Floor Villa Near the Beach w/Balc...

Xanadu D8Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next Hilton Head Island vacation awaits at this adorable, coastal getaway! This trendy villa is...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
New to the Rental Market!

4505 Windsor Court North is a elegantly decorated 2 bedroom, 2 bath villa with unobstructed oceanfront vistas from every room.Located on the 5th floor, the villa has an refreshed kitchen with beautiful granite counter tops, stainless steel...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Bright and spacious home in Sea Pines,  ...

17 Sand Fiddler RdOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal family hideaway in Hilton Head, SC! This immaculate and bright home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Oceanfront Palmetto Dunes condo with ama...

Barrington Court 409Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the beauty of Hilton Head Island from this completely remodeled one-bedroom condo...

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

Hilton Head Tours & Activities

Two Day Surf Board Rental

Hilton Head Outfitters - Bike Rental

Book online
$69.99

Rate Two Day Rental: $69.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 2 Days

Hilton Head Seafood Festival Daufuskie Island History Experience

Step Back in Time on Daufuskie Island Tucked between Hilton Head and the mainland, and accessible only by boat, Daufuskie Island is often described as “the other side of the river” — a hidden gem where time seems to stand still. This...

Private Fireworks Cruise

Hilton Head Yacht Charter Company

Take to the water in style! Rates $5,000 for a private charter, up to 12 people Duration 4 hours About Hilton Head Yacht Charter at night is all about you. Imagine a luxury yacht, designed for ultimate entertainment, slipping through the...

Twelve Day Electric Bike Rental

duration: 12 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...

Two Day Schools

Palmetto Dunes Golf Academy

Book online
$750.00

Duration & Rates - 2 Days, 3 hours of instruction per day - $750 per student About The small group 4:1 student:teacher ratio promotes important quality attention. Skill levels can be mixed and the instructor is able to meet the unique needs of...

Lowcountry Lake Setting

Island Life HH Photography

Book online
$195.00 - $745.00

Photography Lakeside on Hilton Head Island Duration - Up to 60 minutes, with most shoots lasting about 45 minutes About Join us at Jarvis Creek Park on Hilton Head Island for a wonderful Lowcountry Setting like no other. This setting has a...

Surf and Sail Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 min_age: 7 max_age: 15 group_size: Up to 20 Campers description: Join us for an exhilarating 4-day camp combining the thrill...

Saint Helena Sunset Sail

Otter Sailing Adventures LLC

Book online
$375.00

There's nothing like experiencing the magic of a sunset under sail in the beauty of the St Helena sound Duration 2 hours About Private Sailing Charter - Price Per Group (up to 6) There's nothing like experiencing the magic of a sunset...

Full Day Fishing Trip

BackCountry Light Tackle & Fly

Book online
$895.00

Duration 8 Hours About Light Tackle and/or Fly Fishing Experience Explore more localized waters from the Departure Boat Ramp! 375 lbs maximum (all passengers): - 2 Adults - 1 Child, 1 Adult - 1 Adult

PB Sunset Hibachi Dinner Cruise
Book online
$40.00 - $175.00

duration: 2 Hours meeting_point: Chapel Dock pricing: $175/adult $145/children 2-10 $40/children under 2 description: Experience an unforgettable dining experience on a 2-hour Hibachi Dinner Cruise in Palmetto Bluff. Imagine indulging in delicious...

Waddell Mariculture Center Tour

Coastal Discovery Museum Hilton Head

Book online
$25.00

The Waddell Mariculture Center (WMC), located in Bluffton, SC, is a field experiment station of the South Carolina Department of Natural Resources (SCDNR). WMC is one of the largest and most sophisticated facilities for mariculture research in the...

Private Charter (up to 14 passengers)

Island Head- Hilton Head Harbor

Book online
$229.00 - $1,374.00

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