Hilton Head, SC Vacations

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Featured Vacation Rentals

Stunning oceanview condo w/ a shared poo...

Island Club 1403Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Have the vacation of a lifetime with a stay at this pretty, family-friendly condo in the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Sunset Rentals | Villamare 3223

Villamare 3223 is a 2nd floor, 2 bedroom, 2 bath villa in the extravagant Villamare complex at Palmetto Dunes Resort on Hilton Head Island. Savor the best in oceanfront living and amazing resort amenities from the comfort of this warm and welcoming...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunny & bright, dog-friendly condo w/ go...

Inverness 942Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Inverness Village, a complex located near golf courses, beaches, and so much more...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Second-Floor Condo Steps to Coligny w/Sh...

Tanglewood 1005Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Immerse yourself in this freshly remodeled two-floor condo near the beach and leave all of your...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Comfortable 3 Bedroom House with Private...

Welcome to this striking 3-bedroom, 2-bathroom home in Hilton Head island, ideally located near all the fantastic amenities in Palmetto Dunes Oceanfront Resort. It offers a cavernous open living room featuring a queen sleeper couch which makes this...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
4 Bedroom home with luxury finishes and ...

As you enter this handsome home, you are first greeted by its open concept, luxury vinyl plank floor, high ceilings, and crown molding. The living room features two leather couches, a 65-inch intelligent TV, generous natural light from enormous...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Afternoon Wambaw Creek Wilderness Area Tour - 2 Hour
Book online
$52.00 - $104.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

One Week Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$59.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miled of bikes paths.

Hunting Island and the Holidays

Hilton Head Island Recreation Association

Book online
$25.00

duration: 2hrs meeting_point: Hunting Island State Park group_size: Up to 20ppl description: A wonderful Moore to Life Holiday tradition filled with nature, food, shopping and fun with friends! We'll begin our day at the Hunting Island Nature...

Bike Rental • Four Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Rent Bikes and Gear Accessories for your vacation! Duration 4 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Volunteer Open House

Coastal Discovery Museum Hilton Head

Help inspire people to care for the Lowcountry. Adults (18+) are invited to explore how they can contribute their time and talents to support the museum’s mission and foster community engagement. Volunteers are integral to the Museum's mission to...

Surfboard Rentals

Hilton Head Island Recreation Association

Book online
$25.00 - $140.00

duration: 2-8 Hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 description: Our surfboard rentals have you covered! Whether you're a seasoned surfer or just starting out, we offer a wide range of...

Kayak Tour

Port Royal Sound Foundation

Book online
$35.00 - $50.00

duration: 2 Hours description: Join a PRSF Naturalist for a 2-hour guided kayak tour of the Chechessee River departing from the Maritime Center. Children ages 5-12 must be on a tandem kayak with an adult (18+). Designed for all experience...

Two Day Beach Cart Rental

Hilton Head Outfitters - Bike Rental

Book online
$19.99

WIDE ALL-TERRAIN BACK WHEELS provides easy roll over sand HOLDS ALL YOUR BEACH GEARS, carries cooler, beach towels, umbrellas and more! EASY OPEN AND CLOSING, opens in seconds and folds flat for travel and storage MULTI PURPOSE - can be used for...

Three Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

Enjoy miles and miles of scenic bike paths Duration 3 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 ...

Lowcountry Reptiles

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

*The Locals You Haven't Met, Get to Know Your Reptile Neighbors!* ___________________________________ Duration 1 Hour ___________________________________ About This indoor program introduces you to some Lowcountry locals you might not have...

Dolphin Sunset Sail

Salt Marsh Sailing

Book online
$399.00

*Finish the day the most relaxing way possible* ___________________________________ Rates - **Private Charter (Up to 6 People):** $399 ___________________________________ Duration 2 hours and 30 minutes ___________________________________ ...

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