Hilton Head, SC Vacations

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Featured Vacation Rentals

Direct Ocean View Condo with balcony, po...

Summary:Shorewood 211The Space:Welcome to your oceanfront heaven in Hilton Head, SC! This impressive condo offers handsome direct ocean vistas and is ideally located on one of the island's best beaches. With a enormous private balcony, you can soak...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Updated Ground Floor Villa with Golf Vie...

Fairway Lane 104Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the serene surroundings of Hilton Head, SC, this attractively remodeled condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Large Three Bedroom Villa Overlooking th...

You are going to adore staying in this attractively remodeled and impeccably maintained three-bedroom Inverness villa. Thoughtfully designed with a coastal-inspired aesthetic, this home combines comfort, style, and gorgeous golf course vistas for...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Coastal Villa with Shared Pool, Deck & F...

Summary:Beachwalk 123The Space:A comfortable private deck, vaulted ceilings with a skylight, and a pathway to the beach make this Beachwalk villa a memorable locale for a magical holiday.Your villa is located within simple walking distance of the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Incredible villa with pool and tennis ac...

Evian 209Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This rental is a pretty, newly updated villa located in the heart of Shipyard Plantation. This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Amazing Oceanfront estate

NEW TO ISLAND GETAWAY! Set along the shoreline with sweeping Atlantic vistas, this exceptional six-bedroom, 6900 sq foot, oceanfront estate captures the appeal of classic Nantucket style paired with refined coastal luxury. Thoughtfully designed...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 15

Hilton Head Tours & Activities

Flatout Crazy - Inshore/Nearshore Trip
Book online
$350.00 - $1,095.00

description: Best Fishing Guides in Murrells Inlet and Myrtle Beach Area Rates - **Half Day Trips:** Pricing includes 2 passengers - $50 per additional person - **Full Day Trips:** Pricing includes 4 passengers - $75 per additional...

Baby Gear Rental • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $125.00

duration: 2 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

28 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$96.00 - $740.00

duration: 28 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After...

Discovery Flight

Hilton Head Helicopter Tours

Book online
$400.00

duration: 1 Hour (30 minutes flight time and 30 minutes ground) meeting_point: 38 Gateway cirle HHI,SC 29926 min_age: 16 description: Get ready for the adventure of a lifetime with a Discovery Flight! This hands-on experience gives you the...

10 Day Rental

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 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...

Beach Cruiser

Hilton Head Helicopter Tours

Book online
$69.00

description: The Beach Cruiser is a helicopter sightseeing trip that flies over the sandy shores of Hilton Head, offering sweeping coastal views. Guests see landmarks and natural scenery from above, including beaches, creeks, and coastal sounds. The...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

Old Town Bluffton Farmers Market Cruise

Duration 4 Hours About Immerse yourself in the blissful charm of Old Town Bluffton, with this unforgettable excursion down the beautiful May River and get dropped off on the all new Calhoun Street Dock and Park in the heart of it all...

Horse Therapy Sessions

Daufuskie Marsh Tacky Society

Book online
$30.00

description: Groundwork sessions that focus on grooming, basic horse handling, and hand grazing. Duration 30 minutes About Experience therapeutic benefits through the healing power of the horse with groundwork sessions that focus on grooming...

Glow in the Dark Splatter Party! - Premium
Book online
$60.00 - $825.00

duration: 1.5 Hrs meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: It’s your invite to light up the night and vibe out with your crew! Experience the thrill of our glow-in-the-dark parties...

Four Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$220.00 - $524.00

description: Enjoy miles and miles of scenic bike paths Duration 4 Weeks 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...

Shark Tooth Island Excursion

duration: 4 Hours meeting_point: Shelter Cove Marina (next to Ela's) description: *Hunt for Treasures of the Sea!* Enjoy a scenic boat ride from Hilton Head to Savannah, where you will step off onto islands to search for the fascinating artifacts...

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