Hilton Head, SC Vacations

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Featured Vacation Rentals

Peaceful Oceanfront Villa with Pools, Ho...

Island Club 1304Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel a pleasant stay dipping in and out of the pool, playing tennis, or working out at the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Hilton Head Island condo with water-view...

Seascape Villas 3205Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in a dreamy Hilton Head Island hideaway at this Seascape Villas condo. Perched...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Bright Condo with Full Kitchen, Shared P...

Island Club 6202Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take the break you've been waiting for in this enchanting Island Club villa that features an...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3rd row Ocean Luxury - Private Pool/Spa ...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach—just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Ocean View Condo, Tennis, 3 Pools, Beach...

Summary:Hilton Head Resort 1403The Space:NOTICE: The hot water tub is down until further notice. Thank you for understanding.Boasting prime ocean and marsh vistas from the private top-floor balcony, a choice island hideaway awaits at this fresh...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
205 Jacana-\

**Luxurious 6-Bedroom Beach Home Just Steps from North Forest Beach!**Escape to your dream vacation in this cavernous and attractively designed 6-bedroom, 6 full and 2 half bath beach home, just a few sandy steps from the impressive North Forest...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16

Hilton Head Tours & Activities

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

Limited Edition T-Shirts

Historic Mitchelville Freedom Park

Book online
$15.00

pricing: $15 description: Juneteenth Limited Edition T-Shirts

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

SC Pimento Cheese Sponsor

Red Maple Event

Book online
$500.00 - $3,000.00

duration: 5 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: Promote your business in front of the crowds at the SC Pimento Cheese Festival This free, family friendly event will draw crowds from all over the state. There...

Stella

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

SCM WAHHI Outback Page Island

description: *Boating and kayaking in pristine salt marshes!* --- Description One of our signature programs and an exceptional value from Outside! The Outback begins with a guided boat trip where the captain shares stories of the Lowcountry...

Guided Kayak Tour

H2O Sports

Book online
$45.00 - $90.00

duration: 2 hour tour 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: Up to 14...

C - PB Nature Walk

meeting_point: Palmetto Bluff, Bluffton description: MAY RIVER WALK AT THE BLUFF Palmetto Bluff is a nature lovers paradise. This interpretive tour will take a loop route that will mix forested paths as well as paths along the May River all at...

America 250 Hilton Head History Cruise
Book online
$24.95 - $44.95

duration: 1.5 Hours cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 group_size: any size group accessibility: Yes description: Celebrate America’s 250th Anniversary with an...

Italian Club - Private Sunset Dinner Cruise

duration: 2 Hours meeting_point: Hilton Head Island min_age: 13 description: Hilton Head Italian Club - Sunset Dinner Cruise! **Book online now for fastest and most convenient check out.** *Departing from Harbour Town!* Duration 2...

Four Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$600.00

description: Duration 4 Hours ___________________________________ About *Most Popular* Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, King Mackerel, Cobia, Triple Tail, Sharks! (Species Depend On Season, Tide ...

Ultimate Dolphin Experience

Lowcountry Watersports

Book online
$16.95

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