Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Ranch-style home with private pool with ...

Tupelo Road 28Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate your very own slice of heaven with this gorgeous ranch-style getaway. The open layout...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
2 Bedroom Second Floor Oceanfront Condo

They thought of everything when this pretty two bedroom oceanfront villa was being refreshed! Combining an fashonable modern beach design throughout while also focusing on comfort, the best of both worlds collide in this Hampton Place...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Golf course-view condo near beach with p...

Turnberry Village 288Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate a coastal golf hideaway at this fairway-view condo overlooking Palmetto Dunes...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Marriott's Barony Beach - Many Weeks Ava...

***Please use the "Contact Host" located under Check Availability for any reservation questions that you may have.Most high-demand season weeks are offered on a Friday, Saturday, and Sunday check-in & out with SEVEN NIGHT INCREMENTS. HOWEVER, we may...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Large Two Bedroom Villa with Easy Access...

Handsome two bedroom Centre Court villa which is centrally located in Palmetto Dunes Oceanfront Resort! Easily walk to the George Fazio Golf Course, General Store and Robert Trent Jones Golf Course! The kitchen is gorgeously appointed and comes...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3rd-floor villa with pools, tennis & pic...

Ocean Walk Villas 303Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*The outdoor pool area has been completely modernized as of June 2025. The indoor pool...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

One Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$2.00 - $65.99

One Day Bike Rental: - 16” Kids Beach Bike: $25.99 - 20” Kids Beach Bike $25.99 - 24” Youth Beach Bike: $25.99 - 26” Bike w/ Child Seat: $35.99 - 26” Mens Beach Bike: $25.99 - 26” Unisex Beach Bike: $25.99 - 12" Balance Bike: $25.99 ...

Solaris - Sunset Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for 7 to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates...

Ohana Low Country Paddle Festival VIP Cruise

Saturday, September 6th 8:30-11 am Meets at: Rowing and Sailing Center at Squire Pope Community Park 137 Squire Pope Rd, Hilton Head Island SC 29926 The cruise will include: -Custom Pickney Island circumnavigation on the luxury power...

Dolphin Nature Cruise

Island Time Charters

Book online
$325.00 - $399.00

Duration 2 or 3 Hour This is our most popular cruise for a reason! About This Dolphin and Nature Cruise takes you on the waters surrounding Hilton Head Island which inhabit hundreds of Atlantic Bottlenose Dolphins along with, osprey, great...

Private Water Ski Adventure Day (7-12 Passengers)

Island Head- Hilton Head Harbor

Book online
$450.00 - $1,350.00

Come enjoy a day on the water with Island Head! About Come enjoy a day on the water with Island Head! This private experience includes a USCG captain to drive the boat and assist in the water sport of your choice. A tube, water skis, wakeboard...

Pony Rides - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

Tuesday night Firework Sailings

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

About Night time Fire Work sailing charter! More info **Pricing:** • 1-6 people: $600.00 and $100 for each additional person up to 14. ($1,400) • 15-20 people is a flat $1,500.00

Private Morning Sail / dolphin watch on Seas The Moment - newest vessel

duration: 2 Hours cancellation_summary: 72 hour free cancellation meeting_point: 1 Waterway Lane, Hilton Head Island SC 29926 max_age: 90 group_size: Maximum of up to 12 people accessibility: Limited Handicap accessibility, Please call us to...

Saint Helena Day Sail

Otter Sailing Adventures LLC

Book online
$300.00

Experience the awe-inspiring beauty of Low Country waterways and the Saint Helena Sound Duration 2.5 hours About Private Sailing Charter - Price Per Group (up to 6) Experience the awe-inspiring beauty of Low Country waterways and the...

Gullah Celebration Cruise

Vagabond Cruise

Book online
$90.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 80 passengers description: Join us for an extraordinary experience aboard the exquisite Spirit Of Harbour Town, as we embark on a captivating journey this year. Indulge in the...

Adventure Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 30 Campers description: Experience adventure this summer! Participants will make lasting memories of kayaking, stand up paddle...

Trail Rides Experience - Montage Guests

duration: 1.5 hours meeting_point: Longfield Stables Trail Barn min_age: 8 group_size: Up to 5 people description: Embark on an unforgettable experience through the scenic Lowcountry of Palmetto Bluff. Our expertly guided rides take you through...

Find your perfect Hilton Head

Fishing Charter

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