Hilton Head, SC Vacations

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Featured Vacation Rentals

Panoramic views of the inter-coastal wat...

You're going to be thrilled with this modern yet comfortable condominium with expansive vistas of the inter-coastal waterway Broad Creek! Located in Captain's Quarters, you'll be a calming walk away from multiple different eateries and various...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Modern coastal villa with balcony, ocean...

Captains Walk 437Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With oceanfront vistas and access to a calming swimming pool, this Captains Walk condo is the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
7169 Harbourside II with Beautiful Marin...

This penthouse level villa has sweeping vistas of the entire Shelter Cove Harbour Marina. The villa itself consists of two floors. The first floor features an refreshed Queen bedroom and bathroom along with the kitchen, living and dining areas. ...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Unique condo w/ bay view, balcony & spir...

Harbourside 7123Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to something special when you book a stay at this charming condo in Hilton...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Oceanfront villa with partial ocean view...
4.7
(15)

Captains Walk 440Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your vacation in the pool or at the beach when you stay in this gorgeous villa with...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
2-story condo with on-site pool, golf, t...

Harbour Master 503Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make the most of Carolina coastal living at this beautiful Harbour Master condo at Shipyard...

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

Hilton Head Tours & Activities

Luxury Sparkling Wine & Champagne Tasting

duration: 1 Hour min_age: 21 description: Experience the art of celebration with our Luxury Sparkling Wine & Champagne Tasting, where every sip tells a story of elegance, tradition, and terroir. Set against the charming backdrop of Honey ...

Eight Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $275.00

Electric Bike Rental Duration 8 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...

Bike Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

duration: 1 Day cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental drop...

Private Tubing Trip

Island Head- Hilton Head Harbor

Book online
$250.00 - $675.00

Have a blast on a private tubing trip! About This is fun for everyone! Have a blast on a private tubing trip. Our captain will show your group a thrilling time as you tube the beautiful low country. This trip is private to your group and maxes...

Day Camp Sessions

Daufuskie Marsh Tacky Society

Book online
$425.00

Campers learn practical, natural horsemanship and riding skills! Duration 10 minutes About Youth (ages 7-17) are welcome to participate in one or more week long day camp sessions. Campers learn practical, natural horsemanship and riding...

Private Full Day Cruise

Unwritten Charters LLC

Book online
$1,500.00

Come enjoy a couple of hours on the water with us! Duration 6 Hours About This Full Day cruise in the harbor will take you to The Battery, The Ravenel Bridge, and out to Ft. Sumpter. A great way to see Charleston from a completely different...

Flatout Crazy - Inshore/Nearshore Trip
Book online
$350.00 - $1,095.00

Best Fishing Guides in Murrells Inlet and Myrtle Beach Area Rates - **Half Day Trips:** Pricing includes 2 passengers - $50 per additional person - **Full Day Trips:** Pricing includes 4 passengers - $75 per additional person ...

Afternoon Dolphin Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

See the Coastal Wildlife About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Depending on the time of year...

Marsh Critters

Coastal Discovery Museum Hilton Head

Book online
$7.00

*Learn about the creatures of the salt marsh ! Great for families with younger children.* ___________________________________ Rates - **$6 per person aged 3 and up, under 3 Free** ___________________________________ Duration 30 minutes...

Critter Meet and Greet

Coastal Discovery Museum Hilton Head

Drop by the Museum for this casual Meet & Greet to learn about the alligators, snakes, and a few other fun critters that share Hilton Head Island with us. Take this opportunity to see animals up close, gets hands-on and hold a critter or two, take...

Private Afternoon Sail and 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 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we...

Private Sunset & Fireworks Cruise - 16p

This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a beautiful Lowcountry sunset! After the sun goes...

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