Hilton Head, SC Vacations

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Featured Vacation Rentals

Dog friendly condo with pool, central AC...

Summary:Moorings 43The Space:Make your next Hilton Head Island vacation one to remember from the comfortable confines of this handsome condo. This single-level condo combines the amenities of home with immediate access to the beach, a shared pool...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Ocean Overlook - The Ultimate Vacation E...

LUXURIOUS DIRECT OCEANFRONT HOME! UNOBSTRUCTED OCEAN VIEWS! SO CLOSE YOU CAN HEAR THE WAVES CRASH WITH THE WINDOWS CLOSED! DIRECT BEACH ACCESS! POOL ACCESS! ALL BRAND NEW! 3RD FLOORING! CORNER UNIT! PRIVATE BALCONY! OCEAN VIEWS FROM EVERY ROOM...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Two Bedroom Queens Grant Villa wit...

You will be glad you chose this huge and comfortable two bedroom Queens Grant Villa! There is so much space for you to spread out on your vacation at this villa!The kitchen is very sizable and, being entirely outfitted, make it an amazing choice for...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Casual Condo with Shared Outdoor Pool, H...

Summary:HH Beach & Tennis 10AThe Space:Shiplapped walls and a view of the neighborhood lake (from the private furnished balcony) make this condo an ideal casual getaway. The family-friendly space features shiplap accents to help get you in the mood...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Corner condo with panoramic view & wrapa...

Summary:Hampton Place 6209The Space:Get access to one of the best vistas Palmetto Dunes has to offer in this inviting condo on the sand! The wrap-around deck overlooks the vast beach and blue waters of the Atlantic, so you will never want to leave...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Spacious condo with patio, pool, walking...

Summary:Hilton Head Cabanas 3The Space:Welcome to your ideal hideaway in Hilton Head, SC! This gorgeous condo, located in the charming South Forest Beach area, is just steps away from the world-famed Coligny Beach. With refreshed bathrooms and...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Saint Helena Sunset Sail

Otter Sailing Adventures LLC

Book online
$375.00

description: There's nothing like experiencing the magic of a sunset under sail in the beauty of the St Helena sound Duration 2 hours About Private Sailing Charter - Price Per Group (up to 6) There's nothing like experiencing the...

2 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

28 Day Rental

Island Life Rentals and Tours

Book online
$96.00 - $740.00

duration: 28 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...

Private Fishing Charters

Performance Fishing Charters

Book online
$525.00 - $1,400.00

description: Hilton Head’s premiere fishing charter! Duration 3-8 Hour Rentals **Up to 4 people** Possibility for 5 with children About Located on Hilton Head Island, your charter will be guided by Captain John Cloyd, a USCG...

Private Sunset & Fireworks Cruise - 12p

meeting_point: Hilton Head, SC description: 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...

Blue Granite Express

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Guests enjoy a narrated 90-minute trip through Fairfield County countryside. Seating on the train is on board an open-air car, allowing easy viewing as...

Firework Cruise

Island Head - Broad Creek

Book online
$39.99 - $599.00

duration: 1.5 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 description: Firework Cruise Take in the sights of the Shelter...

Full Moon Firelight Kayak Paddle

Vintage View River Retreat

Book online
$10.00 - $35.00

description: A 2.5-hour glowing kayak paddle under the full moon, complete with a glow-in-the-dark fun pack and a cozy campfire with treats on the banks of the Pacolet River in Spartanburg South Carolina.

Private Sunset Cruise (Up to 14 Passengers)
Book online
$549.00 - $899.00

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 14 Passengers description: The private sunset...

Seven Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 7 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...

Genesis Compound Rental & Range Time

duration: 1 Hour Range Time description: Curious about archery but don’t own equipment? Our Genesis Compound Tryout Experience includes everything you need — bow, arrows, and range time — with guidance from our knowledgeable staff. It’s the...

Electric Bike Hourly Rental (Walk Up)

Island Life Rentals and Tours

Book online
$50.00 - $60.00

duration: 1-6 Hours description: *Perfect for your day exploring around Hilton Head!* Additional Rates - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free - **Pick Up** - Free *All rentals must be returned within designated rental...

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