Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Sunset Rentals | Kingston Dunes 58 | Dog...

The ideal Hilton Head vacation starts with finding the ideal Hilton Head vacation rental! Consider it done when you book this 4 bedroom, 4 bath bright and sunny home, located in Hilton Head Island’s Shipyard less than a mile from the beach.To the...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Marriotts Sunset Pointe at Shelter Cove ...

*** Sanitation/Cleaning Update ***Over the next few months, when guests are in hotels within the Marriott portfolio, they will notice a number of additions to our cleaning regimen designed to set an even higher standard of cleanliness for the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
HHI Beach Cozy Condo: Pool, Gym & Tennis

Hilton Head Island Beach & Tennis Resort | Folly Field Beach Park On-SiteLocated in a resort community, just steps from the sugar-white sands along the Atlantic shoreline, this Hilton Head Island vacation rental offers countless beachfront fun. Cool...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
One Bedroom with a Murphy Bed

This beachfront 1 bedroom, 2 bathroom 5th floor villa features magnificent ocean vistas from all windows! When entering the villa, the entirely equipped kitchen is on the right side which is ideal for cooking meals. There is a breakfast bar for two...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Double Master Suite Luxury 4 BR Sea Pine...

Wonderful luxury Sea Pines four bedroom home with private pool and spectacular vistas of the live oaks wrapping around the golf vistas. Beautiful high ceilings with humongous kitchen and tons of living space outdoors. Oversize kitchen and dining...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Ranch Style Hilton Head Island Vacation ...

Welcome to this exceptional ranch-style home that blends Southern appeal with a invigorating coastal interior. Located in the heart of Palmetto Dunes, this unique four bedroom and three bath home features an open floor plan, soaring high ceilings...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

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...

Round Trip Ferry Tickets | 9:30am - 3:30pm | Tuesday - Sunday

Round Trip Ferry Tickets to Daufuskie Island for 9:30am - 3:30pm | Tuesday - Sunday Ride the Daufuskie Island Ferry from Broad Creek Marina on Hilton Head Island to Daufuskie Island! • Depart from Broad Creek Marina on Hilton Head Island at...

Donuts with Santa Cruise

Vagabond Cruise

Book online
$24.95 - $44.95

duration: 60 Minutes cancellation_summary: 48 hours in advance meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 max_age: 99 accessibility: Not Wheelchair Accessible description: **Donuts with Santa Cruise** Experience the joy of the...

Savannah Wildlife Refuge Hike

Hilton Head Island Recreation Association

Book online
$30.00

duration: 3hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Up to 14 people description: Hosted by Moore 2Life. Come explore the Savannah Wildlife Refuge from the comfort and warmth of the Island...

Private Day Sail

BC2 - Island Head

Book online
$900.00 - $2,500.00

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

Six Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$825.00 - $1,220.00

Golf Cart Rentals! Duration 6 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online due to South...

12 Day Rental

Island Life Rentals and Tours

Book online
$48.00 - $335.00

duration: 12 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...

PB Family Fishing - 10 Passenger
Book online
$1,095.00 - $1,320.00

Fishing Fun for the Whole Family! _____________ This trip includes everything you need: Bait and tackle U.S. Coast Guard licensed captain and fishing guide Licensing Iced cooler ___ This trip accommodates up to 10 passengers. Bring the family...

One Month Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$873.00

Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a small motor engages and gives you a boost, so you can zip through...

Creature Feature

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: .75 cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: The Lowcountry is home to an incredible variety of fascinating creatures...

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy beverages of...

Dolphin & Nature Cruise

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

*Opportunity to see bottlenose dolphins, river otters and special species of birds! March through October.* ___________________________________ Duration 1.5 Hours ___________________________________ About Join a museum docent in this cruise...

Find your perfect Hilton Head

Fishing Charter

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