Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

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. Delightful high ceilings with giant kitchen and tons of living space outdoors. Oversize kitchen and dining area...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Ocean Walk 106A | Great Location + Pool ...

Step Inside Ocean Walk 106A & relax! This Hilton Head Island condo offers a restful getaway for up to four guests with one cavernous bedroom and one full bathroom.You'll appreciate the relaxing hues and vibrant pops of color in this upgraded...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
French Home on Golf Course Private Pool ...

Summary:Coastal CharmThe Space:Narragansett 2 Located on the 1st Tee of the Clipper Golf Course in Shipyard Plantation and mins. away from the pristine beaches of Hilton Head Island, this gorgeous French Country home offers a ideal blend of...

  • Hilton Head
  • 4 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Comfortable getaway with pool, full kitc...

Summary:Beach Club BungalowThe Space:Welcome to your ideal hideaway in Hilton Head, SC! This beautiful condo offers a enchanting blend of comfort and convenience, making it an ideal getaway for families and friends. With a roomy layout featuring a...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Sunny resort home in Sea Pines Resort ne...

Summary:Sea Pines Resort 01The Space:Make your next coastal hideaway a breeze when you stay at this Hilton Head Island resort home! This superb home in Sea Pines Resort offers plenty of community perks, like access to a seasonal outdoor pool, a...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Ocean and Marsh View Home with private p...

Summary:Collier Court 4The Space:Welcome to your dream hideaway in Hilton Head, SC! Just 50 feet from the beach path, this striking home offers beautiful vistas of both the ocean and marsh, making it the ideal getaway for families and friends. With...

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

Hilton Head Tours & Activities

Day Rental

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: 1 Day description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Additional Fees - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free (1 lock per 2 bikes) About - Perfect for a day...

2 Week Rental

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks 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...

Weekday 9:30am-3:30pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekday - Golf Cart Rental 9:30am - 3:30pm *Must have valid Driver's License to rent a cart.*

Two Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$40.00 - $200.00

description: Rent with us! Duration 14 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and...

Ohana Low Country Paddle Festival VIP Cruise

description: Saturday, September 6th 8:30-11 am Meets at: Rowing and Sailing Center at Squire Pope Community Park 137 Squire Pope Rd, Hilton Head Island SC 29926 The cruise will include: -Custom Pickney Island circumnavigation on the luxury...

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...

Three Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$159.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Five Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Half Day Flats Fishing (4 Hrs)

Green Heron Adventures

Book online
$550.00

meeting_point: Beaufort and Hilton Head/Bluffton, SC description: Duration 4 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target...

Family Archery Outing with Range Time

duration: 1 Hour Range Time group_size: Up to 2 Adults & 3 Children (under 16 Years old) description: Bring the whole family together for a fun and memorable activity everyone can enjoy. Our family package includes equipment rental and range time...

Tour & Tasting Experience

Hilton Head Distillery

Book online
$34.95

duration: 1 Hour min_age: 21 group_size: Maximum 15 people accessibility: Wheelchair accessible description: Our signature 1-hour Tour & Tasting Experience invites you behind the scenes for a closer look at the craft, history, and rum-making process...

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