Hilton Head, SC Vacations

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Featured Vacation Rentals

Inviting villa with on-site golf, tennis...

Summary:Golfmaster 1301The Space:Your favorite vacation memories will be effortlessly curated when you call Lowcountry Legacy, a pleasant, end-unit Hilton Head villa, your next home away from home! Settle down and savor the sunshine as you practice...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Bright & inviting condo near the beach w...

Bluff Villas 1673Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located right in the heart of South Beach, this 1,200 sq. ft. rental is just steps from the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
The Hedges D1 | Condo in Hilton Head wit...

The Hedges D1Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'So much is within an simple walk of this first-floor condo at The Hedges, from a gorgeous...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Dunes Villas D2 | Villa in Hilton Head w...

Dunes Villas D2Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape the humdrum of everyday life and discover a relaxing and sunny getaway unlike any other...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Water-view townhome with pool & tennis a...

Summary:Townhouse Manor 6The Space:This beautiful 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 appreciate the location, just off the greens of...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Villa w/ Golf Course Views, Walk to Harb...

Located within the Racquet Club Villas in The Sea Pines Resort, this exceptional vacation rental condo is the ideal place to book your Hilton Head hideaway. The handsome high-end unit has 1 bedroom and 1 bath. Savor the community amenities during...

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

Hilton Head Tours & Activities

First Friday Dinners

Victoria Valley Vineyards at Table Rock

Book online
$65.00 - $75.00

duration: 2.5 Hours group_size: Max 30 People description: Join us for an enchanting evening at our First Friday Dinner from 6 pm to 8:30 pm, as we celebrate friendship and good food in the picturesque setting of Victoria Valley Vineyards. This is...

Hilton Head Airport Pickup

Island Head Transportation

Book online
$230.00 - $350.00

duration: 1 Hour group_size: Up to 14 passengers description: Enjoy a seamless and stress-free arrival with our private Hilton Head Airport pickup service. Designed for groups of up to 14 guests, our comfortable transportation includes plenty of...

Cooler and Ice

Lowcountry Watersports

Book online
$15.00

Heritage Tour

Gullah Heritage Trail Tours

Book online
$25.00 - $49.00

description: *Gullah people are known for preserving more of their African linguistic and cultural heritage than any other African-American community in the United States.* ___________________________________ Duration 2.5 hours...

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...

Nightly Rental.   Premium 6 Passenger Electric

meeting_point: PICK UP AND DROP OFF AT RENTAL ADDRESS ONLY description: About 48 volt electric golf cart with 2026 Lithium Battery. Equipped with seat belts, extended top, LED headlights (high and low beam), turn signals, horn, and digital...

21 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$75.00 - $555.00

duration: 21 Days cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

Hilton Head Yacht Charters

Hilton Head Boat Charters

Book online
$595.00 - $1,295.00

duration: Two, Three, or Four Hours cancellation_summary: We need at least 72 hours' notice for a full refund. meeting_point: 43 Jenkins Island Rd, Hilton Head Island, SC 29926 min_age: 12 group_size: Up to 12 People description: This private yacht...

Private Sunset & Fireworks Cruise - 16p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Palmetto Bluff Daufuskie Island History Tour

meeting_point: Palmetto Bluff description: *Catch a glimpse into a fascinating chapter of Lowcountry history* _____________ About Tucked between Hilton Head Island and the mainland - accessible only by boat – the island on ‘the other side...

Charleston, SC to Jersey City

The Bluewater Academy

Book online
$5,250.00

duration: 7 days meeting_point: 3190 Suite C Matecumbe Key Rd, Punta Gorda, FL 33955 description: The Northern Corridor: A Masterclass in Endurance and Extended Passage making Charleston, South Carolina to Jersey City, New Jersey | June 7th...

4.5 Hour Deep Sea Fishing Aboard the Drifter
Book online
$75.00 - $1,000.00

duration: 4.5 hours cancellation_summary: 48 hours meeting_point: 86 Helmsman Way. Please meet at the flag pole at the right side of the marina. pricing: Adults $85 Children 12 and under $75 description: This fishing trip will travel to an...

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