Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Oceanfront Luxury – Newly Renovated 2-...

Step into this captivating top-floor, completely transformed villa and be greeted by the mesmerizing ocean view. Be one of the first guests to experience the ultimate in coastal sophistication. This striking property blends modern luxury with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beachside Townhome | Parking. Pool + Ful...

The Village at Palmetto Dunes offers a casual Hilton Head stay just steps from the beach, with simple access to golf, tennis, pickleball, and breathtaking bicycle paths. Located within Palmetto Dunes Resort, this property places you close to Shelter...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Gorgeous 5 ?? custom home! 5 king suites...

Vacation in luxury in this beautiful home! This 4500 square foot home is designed ideally for multiple families. Just a 3-5 min. walk to the beach, this home has everything you could ask for! With 7 bedrooms, 7 and 2 1/2 baths, 3 living rooms and...

  • Hilton Head
  • 7 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Breathtaking Ocean Views & Heated Pool

Welcome to your coastal getaway! Ocean Dunes 308!! This attractively appointed one-bedroom villa features a full kitchen, a cavernous combined living and dining area with a sleeper couch and a separate bedroom with a comfortable queen-sized bed. ...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Secluded & Peaceful - Vacation Getaway w...

Summary:Island Club 153The Space:With access to a private beach and multiple tennis courts along with a peaceful feeling of seclusion, this one-bedroom condo makes gatherings of family and friends additional special.Surrounded by palmettos, oaks...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Dog Friendly Condo with Lagoon & Golf Vi...

Summary:Evian 160The Space:With a prime location within the 800-acre Shipyard Plantation, this condo at Evian Villas provides a handsome, calming, quintessential experience on Hilton Head Island. Here in the midst of the Shipyard Golf Course and its...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Flyboard 20 Minute

Carolina Hydrofly

Book online
$129.00

description: 20 Minute Flyboard Pro Series Experience What's Included? 15 Min Flight Time. Includes 10 minutes of instruction time, fuel, life jacket, wetsuit, and helmet We advise everyone to arrive at least 30 minutes before your start time...

Sunrise Beach Photography

Island Life HH Photography

Book online
$225.00 - $775.00

duration: Up to 60 minutes cancellation_summary: Full refund if we cancel due to weather; no refund or discount for late arrival meeting_point: 55 Starfish Dr, Hilton Head Island, SC 29928 description: Get your photo taken on the beautiful Hilton...

Santa’s Twilight Express

The South Carolina Railroad Museum

Book online
$27.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual twilight holiday ride. Santa walks through the train and comes to you—no lines! As we travel down the tracks, the...

19' Stingray Rental

H2O Sports

Book online
$325.00 - $750.00

duration: 2-6 hour rentals cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Boat holds 6...

Cake Decorating

Color Me Greenville

Book online
$50.00 - $450.00

duration: 1 Hour 30 Minutes meeting_point: Color Me Greenville description: 1hr long party. Join us to decorate your own 5” cake! Booking includes unlimited buttercream, fondant, and sprinkles!

4 Day Rental

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

PVT Sunset Dolphin Cruise 16pk
Book online
$695.00 - $1,350.00

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane description: Looking for a private memorable evening on the water? Our Sunset Dolphin Cruise in Hilton Head is the perfect choice. This 90-minute private tour...

Private Sunset Cruise (Up to 34 Passengers)
Book online
$998.00 - $1,497.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 34 Passengers description: Enjoy the Sunset...

One Month Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$80.00 - $400.00

description: Rent with us! Duration 30 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and...

Gift Card

Drifter Excursions

description: Purchase the perfect gift: a gift card with a value of your choosing!

Outside DMC Partner Outing - Hilton Head Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

Lowcountry Marsh Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if reschedule cannot be arranged. meeting_point: 59 Shelter Cove Lane, Hilton Head Island, SC description: Join us along the Lowcountry...

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