Hilton Head, SC Vacations

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Featured Vacation Rentals

Large Three Bedroom Villa Steps from the...

This three bedroom, three bathroom villa will be ideal for next family or group outing! Steps from the pool and mere mins. from the beach, this sizable villa will provide ample space for your family to spread out and relax!The kitchen has been...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Oceanfront Views, Recently Updated, Thre...

This third floor handsome condominium, within the Captain's Walk community, has direct oceanfront vistas that will not disappoint.The kitchen to the left as you enter, comes completely-supplied to meet all of your needs during your calming stay...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Newly Renovated Harbour Town Villa with ...

Summary:Ketch Court 824The Space:Ketch Court 824 is conveniently located in the heart of Sea Pines. This freshly remodeled villa features all new furnishings throughout, as well as a roomy, private patio with two outdoor seating areas. The entirely...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Oceanfront, Pool, Views, Luxury, Elevato...

31 Singleton Beach Place in Hilton Head Island, South Carolina epitomizes luxury living at its best. With over 5,500 square feet of living space, this 6-bedroom, 9-bathroom residence offers an unparalleled level of comfort and sophistication. Upon...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Wonderfully Decorated Two Bedroom Water ...

This two bedroom Water Oak villa is the embodiment of the beach experience. The attention to detail throughout this amazing villa is seen in every space from the beach modern decor and paint to the elegant bathrooms. The kitchen is wonderfully...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Beautiful Palmetto Dunes Villa- Lagoon V...

Summary:Queens Grant 762The Space:Welcome to your serene hideaway in Hilton Head, SC! This striking three-bedroom, three-bathroom villa is located within the photogenic Palmetto Dunes' 11-mile lagoon system, offering a ideal blend of relaxation and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Adopt-a-Nest

Coastal Discovery Museum

Book online
$25.00 - $75.00

description: About Adopting a Loggerhead Sea Turtle nest will provide the Coastal Discovery Museum’s Sea Turtle Protection Project with important funds to help support the educational portion of the project and the sea turtle exhibit at the...

DIY Custom Sneaker Painting

Color Me Greenville

Book online
$45.00

duration: 3 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 pricing: Charms and Accessories vary in prices. You can view our options in person along with pricing.: Shoe Charms:($1-$10) Color laces: Variable ($2-$10) Pre-made...

One Week Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Rate 7 Day Rental: $149.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration One Week (7...

Black & Blue Fishing Charters

Black & Blue Charters

Book online
$425.00 - $1,700.00

description: Black & Blue Duration & Rates **Three Hour Fishing Charter** - $625.00 *Will catch mostly sharks* **Four Hour Fishing Charter** - $750.00 *Most popular for families* **Five Hour Fishing Charter** - $900.00 *Catch your...

Island Happy Hour Cruise

Daniel Island Ferry

Book online
$18.00 - $38.00

duration: 75 minutes meeting_point: description: Friday Happy Hour Cruise on the Wando River Every Friday | 4:00 PM – 5:15 PM Start your weekend on the water aboard Daniel Island Ferry's Friday Happy Hour Cruise. This relaxing 75-minute cruise...

Two Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$445.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Four Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 4 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...

2.5 Hour Firework Tour

Hilton Head Island Tours

Book online
$425.00

description: *Learn about our Coastal Ecology on our 2hr Private Crabbing Excursion!* ___________________________________ Rates **Private Charter** - $425.00 *(Up to 6 passengers)* ***All ages welcome! | Maximum of 1200...

2026 Juneteenth Food Truck Vendor Registration

Historic Mitchelville Freedom Park

Book online
$206.00

duration: June 13th from 10am- 4:00pm description: **Vendors can sell all food items. Can not sell beverages.** We invite local artists, crafters, food vendors, and nonprofit organizations to join us for a day of culture, history, and community at...

Private Kayak Date Tour

Crooked Creek Kayaks

Book online
$175.00

duration: 2 Hours group_size: Maximum 2 people description: Enjoy exclusive, private guided access into Jarvis Creek’s quiet, winding estuarine waterways — reserved solely for your group and led by your own personal guide. This tailored...

Kayaking & Coffee

Lowcountry Watersports

Book online
$49.00 - $98.00

duration: 1.5 Hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 description: Let our experienced...

SC Pimento Cheese Festival Merch
Book online
$2.00 - $18.00

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