Hilton Head, SC Vacations

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Featured Vacation Rentals

Renovated lagoon view villa with balcony...
4.8
(4)

Seascape Villas 3040Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located beside a striking lagoon, this coastal-chic villa offers a enchanting getaway for...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Cozy Third-Floor Condo w/ Fast WiFi & Ba...

Fiddlers Cove 11JOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located just a short walk from Folly Field Beach and conveniently close to grocery stores...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Very peaceful and tranquil setting.
4.3
(4)

In a peaceful and calming setting, this 3 bedroom, 4 bath townhouse villa, has marvelous vistas of the Robert Trent Jones Golf Course. The living area has wood floors and the furnishings are comfortable. The dining area is adjacent to the living...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Sunlit Sea Escape with Al Fresco Dining,...
4.7
(7)

Greens 152Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to an action-packed vacation when you stay at this beautiful condo on the island of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
North Forest Beach home with a private p...

Luna Sea EstateOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This newly constructed, North Forest Beach ocean home is ready to host all of your favorite...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
Sunset Rentals | Gloucester 79
4.5
(4)

Make cherished memories that will last forever when you treat your family to an island vacation in this 4 bedroom, 3 bathroom vacation home located in the charming Shipyard Plantation on Hilton Head Island. Gloucester 79 is a gorgeous Shipyard home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Three Hour Dolphin Strand Feeding Search

Hilton Head Island Tours

Book online
$375.00 - $395.00

*Dolphin Strand Feeding is a unique and exciting behavior developed by local Atlantic Bottlenose Dolphins!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages...

Daufuskie Island to Hilton Head

Island Head - Broad Creek

Book online
$10.00 - $30.00

duration: 45 Minute Ferry Time cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Freeport Marina Daufuskie Island, SC description: Daufuskie Island Daily Return Trip We offer...

Santa Elena Society

Coastal Discovery Museum

Book online
$25.00 - $1,000.00

*Donate Today!*

Dolphin Eco Tour

Captain Moto Adventures

Book online
$325.00

Duration 2 Hours About Not just your everyday dolphin tour. This is a private tour for the family. Learn about the local ego system and see dolphins. What to bring - BYOB - Sunglass - Sunscreen *No spray lotion* - Appropriate clothes...

Pony Rides - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

Island Head Inshore Fishing

Island Head - Broad Creek

Book online
$495.00 - $1,125.00

duration: 3 - 8Hours description: Join us for an unforgettable inshore fishing adventure aboard our 21-foot Parker center console. Whether you're a beginner or an experienced angler, our trips are tailored for fun, excitement, and reeling in the...

Vanishing Mile Isle Tour

Cross Island Cruises

Book online
$369.00

Bring your family on this private excursion to Grenadier Shoals, the famed “vanishing island” sandbar at the mouth of the Calibogue Sound. Duration 2 hours, 30 minutes Rates **Private Charter:** $369 Call to Book only November...

Three Week Electric Bike Rental

duration: 21 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Discovery Night at the Museum

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $40.00

*Hands-on fun! Programs vary weekly.* ___________________________________ Duration 1 Hour - 2 Hours ___________________________________ About ____________ There is something special happening AFTER HOURS at the Coastal Discovery Museum...

Baby Gear Rental Package • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$165.00 - $210.00

Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 72 Hours About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Behind-the-Scenes Series

Coastal Discovery Museum Hilton Head

Book online
$10.00 - $20.00

Take a peek behind the scenes at the Coastal Discovery Museum and get an up-close look at various areas of the museum and Honey Horn grounds with an experienced staff member. These exclusive tours offer access to areas and insights not available to...

Private Water Ski Adventure Day (7-12 Passengers)

Island Head- Hilton Head Harbor

Book online
$450.00 - $1,350.00

Come enjoy a day on the water with Island Head! About Come enjoy a day on the water with Island Head! This private experience includes a USCG captain to drive the boat and assist in the water sport of your choice. A tube, water skis, wakeboard...

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