Hilton Head, SC Vacations

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Featured Vacation Rentals

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
Hilton Head | Harborfront Family Stay | ...

Escape to the coastal appeal of Marriott's Harbour Point at Shelter Cove, a calming waterfront getaway overlooking impressive Broad Creek in Shelter Cove Harbour. Centrally located on Hilton Head Island, this family-friendly resort places you close...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
60 Lawton Rd: Sea Pines

Welcome to the 5BR/4BA BESTNEST at 60 Lawton Road. Gorgeously refreshed and filled with natural light, this five-bedroom Sea Pines home offers generous gathering spaces, flexible accommodations, and a private pool overlooking the lagoon. A separate...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
4 BR Private Home Close to South Beach M...

6 Beachside Drive | One Minute Walk to the Beach*4 Bedrooms | 3 Bathrooms*Sleeps 8*1 King, 1 Queen, 4 Twins*3 TVs | DVD | Alexa | Wi-Fi | Keurig*8 Beach Towels for Guest Use*Beach Gear Credits Included *Savor Rounds of Golf & Kids's Activities with...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Recently Renovated with Open Concept!  O...

This definitely marvelous villa is located within the Queens Grant Community in Palmetto Dunes. The kitchen was completely remodeled and is now an open concept! All appliances are high-quality stainless steel and the cabinets are bespoke tailored...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Island condo with beach access and balco...

Summary:Villamare 2319The Space:Appreciate all the amenities of home at this Palmetto Heaven. The fashonable furnishings and tasteful decor create a pleasant ambiance for a group of friends or the entire family. with a full kitchen, mealtimes will...

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

Hilton Head Tours & Activities

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Pontoon Rental

Island Head - Broad Creek

Book online
$225.00 - $2,200.00

duration: 2 - 9 Hour Rentals (20 Hour Season Pass Also Available) 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: Pontoon...

Luxury Pontoon Rental with Fireworks Experience

description: Fireworks Pontoon Party Boat Rental and private VIP box for Harbourfest Fireworks Show! Captain your own adventure as you head out on a 2-hour self-guided cruise on a luxurious Bentley pontoon boat. Return to Shelter Cove Marina no...

Solaris - Palmetto Bluff Charter

duration: 2 Hours meeting_point: Palmetto Bluff group_size: Private Charter for up to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates 1-6...

Private Sunset Sail and dolphin watch on Seas The Moment - newest vessel

duration: 2–2.5 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...

Two Day Schools

Palmetto Dunes Golf Academy

Book online
$750.00

description: Duration & Rates - 2 Days, 3 hours of instruction per day - $750 per student About The small group 4:1 student:teacher ratio promotes important quality attention. Skill levels can be mixed and the instructor is able to meet the...

Memberships

Coastal Discovery Museum

Book online
$100.00 - $1,000.00

description: All Members Receive Invitations to members-only seasonal programs Invitations to exhibit openings Advanced notice of upcoming events and lectures Monthly membership bulletin Discounts in the Museum Store $100 Supporting...

Ten Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$78.60 - $187.10

description: Enjoy miles and miles of scenic bike paths Duration 10 Days About Free locks with all rentals. Baskets and helmets also available - please select during check-out! More info Free locks with all rentals - please select...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time Each Way 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: Hilton Head -> Daufuskie Island...

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...

Creature Craft

Coastal Discovery Museum Hilton Head

Book online
$5.00

description: Family Friendly hands-on indoor experience. ___________________________________ Rates - **$5 per craft.** ___________________________________ Duration Stop in anytime between 1:30 and 3:00pm to make your Creature...

Guided Tours

Historic Mitchelville Freedom Park

Book online
$15.00

duration: Approximately 45min description: Step back in time and immerse yourself in the rich history of the first self-governed town of formerly enslaved people in America. At Historic Mitchelville Freedom Park, our guided tours offer visitors an...

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