Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront condo with pools, hot tubs, W...

Seacrest 1101Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'**Planned Roofing Project at SeaCrest. Please review the timeline and key impacts below so you...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Vibrant townhouse with WiFi & pool - sho...

Stoney Creek 261Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'f you savor balconies with a view, a pool on the property, and a location close to the beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Lovely villa with central AC, and easy b...

Bluff Villas 1733Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Harbor vistas and marina access are just some of the reasons why this Bluff Villas condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Family-friendly villa w/ golf course vie...

Water Oak 15Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Water Oak 15 offers fairway vistas of the adjacent Robert Trent Jones Golf Course and is just a...

  • Hilton Head
  • 4 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
SeaPines, Walk to the Beach Club, Update...

You'll adore the privacy and updates in this roomy end unit in Wildwood Spa, a private little neighborhood just ten mins. on foot to the Sea Pines Beach Club. This Premier Property features two bedrooms and an added loft area with a trundle beds...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Welcoming Condo with Lagoon Views, Deck,...

Beachwalk 142Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beachwalk 142 is an ideal spot for athletes because the property has options for basketball...

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

Hilton Head Tours & Activities

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...

Full Moon Float

Vintage View River Retreat

Book online
$15.00 - $45.00

duration: Hourly meeting_point: 250 Phifer Line Rd, Spartanburg SC 29307 description: Full Moon Float with Vintage View Adventures is pure moonlit magic on the Pacolet River! Join us for a twilight paddle as the sun sets and the full moon rises...

Two Day Bike Rental

Wheelz of Hilton Head

Book online
$35.00 - $70.00

Two Day Bike Rental Rates Duration 2 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 getting around town...

Beach photography Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

Short and to the point Duration 10 to 15 minutes About If you are looking for a photoshoot but don’t want that many photos or have kids or grandfathers that will not be able to handle a full shoot we now have our mini beach shoots...

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

One-of-a-kind photo opportunity in a beautiful Lowcountry setting at the Stoney Baynard Ruins Duration - Up to 60 minutes, with most shoots lasting about 45 minutes Overview Are you looking for the perfect Hilton Head family...

Twelve Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $450.00

Electric Bike Rental Duration 12 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Deliberately Unpredictable: Art Beyond Tradition

Coastal Discovery Museum Hilton Head

duration: various description: Main Gallery Exhibit what_is_included: Art from Cindy Chiappetta, Arla Wible, Vickie Jourdan, Sharon Licata, Mark Larkin, Margaret Crawford, Jo Dye, Earline Allen, Donna Varner, Joanna Chalson, John Crum and Linda Tully

PB Family Fishing - 6 Passenger
Book online
$745.00 - $795.00

Fishing Fun for the Whole Family! _____________ This trip includes everything you need: Bait and tackle U.S. Coast Guard licensed captain and fishing guide Licensing Iced cooler ___ This trip accommodates up to 6 passengers. Bring the family...

2 Hour Beachcombing Dolphin Tour
Book online
$45.00 - $650.00

duration: 2 hour tour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Five Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

Enjoy miles and miles of scenic bike paths Duration 5 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

Discovery Flight

Hilton Head Helicopter Tours

Book online
$400.00

duration: 1 Hour (30 minutes flight time and 30 minutes ground) meeting_point: 38 Gateway cirle HHI,SC 29926 min_age: 16 description: Get ready for the adventure of a lifetime with a Discovery Flight! This hands-on experience gives you the...

Three Day Electric Bike Rental

duration: 3 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...

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