Hilton Head, SC Vacations

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Featured Vacation Rentals

Golf Course-Adjacent Villa w/ Fast WiFi,...

Waterford B1Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find your way to the fairway at this beautiful and sunlit vacation rental on Hilton Head Island...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunset Rentals | Captains Walk 416

If beach strolling is one of your passions, look no further for the ideal island accommodations. This 2 bedroom and 2 bath Captains Walk villa is located on the 3rd floor of building one. New wood cabinetry and granite counters can be found...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Wonderful condo right up from the beach ...

Island Club 6203Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just steps away from the beach and with vistas of the lagoon from the private, furnished...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Panoramic views of the Atlantic Ocean fr...

Appreciate one of the best oceanfront vistas anywhere on Hilton Head Island. This gorgeously appointed two bedroom oceanfront condominium is focused on comfortability and accentuating the incredible vistas. The primary bathroom was just remodeled...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Gorgeous home with new pool in Sea Pines...

HILTON HEAD ISLAND. This handsomely decorated home, located in the heart of the Historic Sea Pines, and is located within walking or cycling distance to Harbour Town, and just steps from the course of Harbour Town Golf Links.As you step inside this...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Lighthouse Tennis Villas  - Walking Dist...

Escape to this spectacular 1-bedroom villa in Hilton Head. Unwind in the comfortable living room with brand new furnishings, a cozy couch bed, and relax in the upsized bedroom with a extravagant king bed. Savor all the amenities of home, this...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Sunset Cruise

Captain Moto Adventures

Book online
$350.00

Join us for a sunset on the water! Duration 2 Hours About Join us for a beautiful sunset cruise. The boat confortable seats 6. All ages and families welcomed on this private charter. What to bring ...

Baby Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $150.00

Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 4 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Lake Wiley Boat Rental

Enjoy a fun day in the sun! Duration 8 hours About This boat is perfect for a fun day in the sun! Located at Lake Norman in Charlotte NC! Specifications - Year: 2016 - Length: 22ft - Make: Bennington ...

Eight Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$65.99 - $131.99

8 Day Rental Rates: - 16” Kids Beach Bike: $65.99 - 20” Kids Beach Bike $65.99 - 24” Youth Beach Bike: $65.99 - 26” Bike w/ Child Seat: $80.99 - 26” Mens Beach Bike: $65.99 - 26” Unisex Beach Bike: $65.99 - 12" Balance Bike: $65.99 ...

Rosie

Slow Rides LLC

Book online
$300.00 - $5,000.00

Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. North East...

Sport Crabbing Adventure
Book online
$10.00 - $1,000.00

Join us for a Sport Crabbing Adventure! Duration 1 hour 45 minutes Tour About Our Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on vacation! Well … maybe not...

Adventure Camp

Hilton Head Island Recreation Association

Book online
$275.00

duration: 4 days • 3.5 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 30 Campers description: Experience adventure this summer! Participants will make lasting memories of kayaking, stand up paddle...

Ohana Sunset Dolphin Cruise
Book online
$45.00 - $2,500.00

Explore the marsh and enjoy the view of the incredible Lowcountry sunset! --- Join us for this 90-minute tour to learn about the salt marsh and search for local dolphins aboard the luxury catamaran, Ohana! Guests are welcome to bring snacks and...

Baby Gear Rental Package • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$165.00 - $210.00

duration: 3 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...

One Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$60.00

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...

Sunset Cruise

Island Time Charters

Book online
$350.00 - $450.00

The most spectacular views and vivid colors! Duration 2 or 3 Hours About This Sunset Cruise allows access to the best locations in the Low Country to enjoy the breathtaking views. With the sunset on one side of the boat and a view of the...

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton Head Island as...

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