Hilton Head, SC Vacations

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Featured Vacation Rentals

Water view retreat Villa with balcony, b...

Summary:HH Beach & Tennis C12The Space:Hilton Head's palm-lined appeal awaits at this enchanting resort-style villa! Overlooking serene water vistas, the villa is well-refreshed and bright, furnished with modern appliances and nautical mementos. A...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Water-view townhome with pool & tennis a...

Summary:Townhouse Manor 6The Space:This classy Shipyard townhouse offers a comfortable, refreshed home base just a short walk from all the best Hilton Head has to offer. Golfers in the group will adore the location, just off the greens of the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Nicely Appointed Home with Lagoon Views!

Updates abound in this enormous home featuring a private saltwater pool, delightfully located on Palmetto Dunes’ spectacular 11-mile lagoon system. Upon entry, the home opens to a sweeping open-concept layout with handsome tile floors throughout...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Condo with Coligny Beach views, outdoor ...

Summary:Breakers 237The Space:Feel the ocean breeze on your face from the comfort of a comfortable condo in Hilton Head Island! This beach-view condo, located in The Breakers Resort, is the ideal home base for beach lovers of all ages. Appreciate...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Inviting Coastal Villa/ Short Walk to th...

Fiddlers Cove 15FOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the Fiddler's Cove Beach & Racquet Club, this striking and peaceful Hilton Head...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Beautiful Colonial-style Home with Lagoo...

What's not to appreciate with this well thought out home and all it has to offer? All three bathrooms just finished remodel in April 2024! The first floor consists of a sizable living room with ample beach-modern furnishings providing seating for...

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

Hilton Head Tours & Activities

Solaris - Sunset Cruise

Vagabond Cruise

Book online
$595.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book the ultimate luxurious charter departing Harbour Town aboard the all new Solaris! **This private charter option accommodates...

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

description: Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of...

Hilton Head Full Moon Cruise

Island Head - Broad Creek

Book online
$59.99

description: Get on the water under a low country full moon! Duration 90 minutes About This is a one of a kind experience to see a full moon from the water. Enjoy a 90 minute slow cruise as you take in the beauty of the low country in a...

Baby Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $175.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 5 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

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...

Private Sunset Cruise (Up to 14 Passengers)
Book online
$549.00 - $899.00

duration: 2 or 3 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers description: The private sunset...

Gullah Heritage Trail Tour

Coastal Discovery Museum Hilton Head

Book online
$20.00 - $49.00

duration: 2.50 description: Duration 2.50 Hours About Book a tour with our partners Gullah Heritage Trail Tours and take a bus trip around the island to learn about their cultural heritage. The tour guides are all Native Islanders whose...

Memberships

The South Carolina Railroad Museum

Book online
$20.00 - $400.00

pricing: - **Family (4 People) Membership:** $50.00 - **Individual Membership:** $30.00 - **Senior (62+) Membership:** $25.00 description: When you join as a member of the South Carolina Railroad Museum, you’re ensuring our museum and railway are...

13 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$95.99 - $191.99

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...

Signature Catering & Events by SERG x Island Head

duration: 2 Hours meeting_point: 18 Simmons Road at Broad Creek Marina min_age: 21 description: One night only — sip your way through a hand-selected wine tasting paired with bites from Signature Catering & Events by SERG. All aboard our luxury...

Beach Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Everything you need for a fun and comfortable day at the beach! Duration 5 Days About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than...

Sunset Cruise

Captain Moto Adventures

Book online
$350.00

description: 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...

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