Hilton Head, SC Vacations

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Featured Vacation Rentals

Stunning home lagoon views and close to ...

Summary:Serene SpartinaThe Space:Located in the heart of the esteemed Sea Pines Resort in Hilton Head, SC, this cavernous home offers a sought-after location with a shared neighborhood pool and tennis courts a short drive away. With an open floor...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Family friendly home with an ocean view ...

Summary:Villamare 1410The Space:Make your next trip to Hilton Head Island an exceptional one by staying in this beautiful home in the Palmetto Dunes Resort! Only walking distance to the beach, and with charming vistas of the Atlantic Ocean right...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Pet friendly condo on golf course, near ...

Summary:Shipmaster 703The Space:Welcome to your ideal hideaway in Hilton Head, SC! This appealing condo, located in the esteemed Shipyard Plantation, offers a ideal blend of relaxation and adventure. You can relax on the outdoor patio equipped with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Secluded getaway: private hot tub & deck...

Kingston Cove 14Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away in the secluded gated community of Kingston Cove at Shipyard Plantation, this...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Homey second-floor villa with admittance...

Summary:Evian 285The Space:Savor the best of Hilton Head at this roomy second-floor villa, located just steps from the island's sandy beaches. You’ll be within striking distance of a lagoon, a golf course, a shared pool, and the ocean, making this...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Secluded Sea Pines retreat with private ...

Summary:Royal RetreatThe Space:Escape to this luxury estate boasting two separate poolside structures and ample seating areas inside and out - ideal for entertaining. The roomy and beautiful property is under new ownership and has been thoughtfully...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 20

Hilton Head Tours & Activities

Gift Card

Wheelz of Hilton Head

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

Santa Elena Society

Coastal Discovery Museum

Book online
$25.00 - $1,000.00

description: *Donate Today!*

Shark Fishing Trips

Top Shot Sport Fishing

Book online
$500.00

description: Rates - 3 hour Trip- $500

SCM Shark Fishing
Book online
$495.00 - $625.00

meeting_point: Hilton Head Island, SC description: *Catch a shark and get out on the water at the same time!* --- There are few things more exciting than hooking a shark! Our three-hour evening shark fishing excursion includes boat, bait...

Fireworks Cruise

BC2 - Island Head

Book online
$89.00

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Corporate Parties & Team Building

Color Me Greenville

Book online
$50.00 - $400.00

duration: 1.5 Hours cancellation_summary: 7 Days meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: 1.5 hours active painting for groups of people. Includes a 11”x14” premium canvas for each attendant plus a 18”x24”...

Hilton Head Yacht - Dinner Cruise

Salt Shaker Charter LLC

Book online
$4,900.00 - $8,000.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: An Evening Aboard Salt Shaker: Gourmet Dining Meets Sunset Serenity! Aboard Salt Shaker, every moment is...

22' Pontoon 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 11...

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

Daufuskie Island to Hilton Head

Island Head - Broad Creek

Book online
$10.00 - $30.00

duration: 45 Minute Ferry Time cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Freeport Marina Daufuskie Island, SC description: Daufuskie Island Daily Return Trip We offer...

Three Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$149.99 - $175.99

description: Single Kayak Full Day Rental: $149.99 ________________________________ Double Kayaks Full Day Rental: $175.99

Eight Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$70.99 - $141.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

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