Hilton Head, SC Vacations

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Featured Vacation Rentals

Second-Floor Villa Near the Beach w/Balc...

Xanadu D8Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next Hilton Head Island vacation awaits at this adorable, coastal getaway! This trendy villa is...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Lovely townhome with balcony, tennis & W...

Ketch Court 821Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your next Hilton Head vacation playing tennis, practicing your drive, and calming on the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Dreamy Island Gem W/ Golf Course View, P...

Heritage Villas 2229Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An memorable island vacation is never a bad idea especially when it comes to being perched...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Renovated home with private screened poo...

Carolina CottageOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend balmy days outside swimming in the screened backyard pool, barbecuing at the lagoon's...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
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
Fabulous! Huge 5 Bedrm/5 Bath Moss Creek...

Moss Creek House Description This 4,500+ sq. ft. home, consisting of 5 bedrooms and 5 baths, that sleeps 12, is located in the impressive Moss Creek private club community. We have an in-ground, plunge pool with lion head water spouts, with the...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

21 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$75.00 - $555.00

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 hours self pick up and drop off available. Attendant will text you lock...

Private Sunset Cruise

Unwritten Charters LLC

Book online
$600.00 - $900.00

Enjoy a Beautiful Sunset Cruise! Duration 2 or 3 Hours About Unwritten Charters will provide bottled water and soda. You and your guests are welcome and encouraged to bring on board your own food and adult beverages (for those 21 and up) for...

Dolphin Cruise

Carolina Breeze Charters

Book online
$275.00 - $350.00

duration: 2 and 3 hour options meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Discover the best of beautiful Hilton Head Island, SC aboard the Carolina Breeze, a 31-foot...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

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 in Coligny...

Spooky Snakes & Crafts

Hilton Head Island Recreation Association

Book online
$15.00

duration: 1.5hrs meeting_point: Rowing and Sailing Center min_age: 4 max_age: 8 group_size: 12 people description: Come join Moore To Life and Island Rec Center for Spooky Snakes & Craft, a hands-on adventure where kids ages 4–8 can discover the...

Lighthouse Tour

Hilton Head Helicopter Tours

Book online
$369.00

Come see this magnificent fort, beaches and property from the air! Duration - **40 minutes** About - Along the way you will see old lighthouses, breath-taking coastal views of the Low Country, and small remote islands only few have ever...

Secure Your St. Lucia Date

Hilton Head Yacht Charter Company

Book online
$500.00

Three Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$15.00 - $60.00

duration: 3 day bike rentals cancellation_summary: NO REFUNDS OR RAINCHECKS meeting_point: your address description: Bike rentals for a three day period. (Example: you rent the bikes on monday, they are due back thursday morning) what_is_included...

Single Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$10.00 - $25.00

First come first serve basis, come into shop to rent! Rates - **Uninsex Adult Beach Cruise Bike Rental:** $20 - **Men's Tall Frame Bike Rental:** $20 - **Tandem Bike Cruise Bike Rental:** $25 - **Trike with Basket Rental:** $25 - **24" Kids Fuji...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$75.99 - $151.99

10 Day Rates: - 16” Kids Beach Bike: $75.99 - 20” Kids Beach Bike $75.99 - 24” Youth Beach Bike: $75.99 - 26” Bike w/ Child Seat: $90.99 - 26” Mens Beach Bike: $75.99 - 26” Unisex Beach Bike: $75.99 - 12" Balance Bike: $75.99 - Adult...

2 Day Rental

Island Life Rentals and Tours

Book online
$18.00 - $100.00

___________________________________ 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...

Baby Gear Rental • Two Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $100.00

Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 2 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

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