Hilton Head, SC Vacations

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Featured Vacation Rentals

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4505 Windsor Court North is a gorgeously decorated 2 bedroom, 2 bath villa with unobstructed oceanfront vistas from every room.Located on the 5th floor, the villa has an refreshed kitchen with elegant granite counter tops, stainless steel...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Lagoon views, shared pool and easy acces...

Summary:Blue Oasis Anchorage 7444The Space:Located in the heart of Hilton Head Island, this striking condo offers an abundance of natural light and gorgeous vistas of the lagoon, creating a serene and inviting ambiance for your vacation getaway...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beautiful Palmetto Dunes Villa- Lagoon V...

Queens Grant 762Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene hideaway in Hilton Head, SC! This gorgeous three-bedroom...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
5 Henry, Close to Beach, Pet Friendly, F...

5 Henry Lane, Hilton Head Island is a home located in Singleton Beach, this gorgeous 4-bedroom, 4.5-bathroom home offers a ideal hideaway. With a roomy patio area featuring a secondary refrigerator, ample seating, pool, private gas grille, and TV...

  • Hilton Head
  • 4 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Ocean Views from Patio! Beautifully upda...

Curlew 8Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Curlew 8 is a extravagant second-row private home featuring ocean vistas and chic, coastal décor...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 28
Island gem with shared amenities, pond v...

Island Club 6205Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take a break from it all and make the best memories at this second-floor condo in the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Night Life Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: Join us for this 35 minute interactive bike tour while riding on glowing bicycles! Duration 35 minutes About Join us for this interactive bike tour while riding on bicycles that glow in the dark. Perfect for...

Sunset Dolphin Cruise

Island Life Rentals and Tours

Book online
$55.00 - $660.00

duration: 2 Hours group_size: 12 - 14 Max description: What could be more peaceful and romantic than a beautiful sunset cruise on the calm evening waters around Hilton Head Island. Share this experience with your loved ones and create memories to...

Southbay Pontoon

Santee Boat Rentals

Book online
$350.00 - $500.00

description: Book our Southbay Pontoon today! Duration: - Full Day (8 Hours) - Half Day (4 Hours) About: The Southbay pontoon boat is a 20ft pontoon boat with a 90hp Suzuki to get you around the lake. With that being said the 90hp has...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

description: Come and discover the Hidden, but not Forgotten Treasures of Historic Bluffton. Duration 45 Minutes About We will discover long lost Hidden Treasures in and around Beautiful Old Town Bluffton. More info There is a 4 person...

4th of July Fireworks Cruise

Drifter Excursions

Book online
$25.00 - $50.00

description: *Fourth of July – Join us for the spectacular Harbour Town display.* ___________________________________ Rates - **Adults** - $50 - **Kids** - $25 - **Babies** - Free! ___________________________________ About - To view the...

Fall Speaker Series: Legends & Luminaries of Hilton Head Island

duration: 1.5 hrs cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: Join the Coastal Discovery Museum as we commemorate our 40th...

One Day (24-Hour) Golf Cart Rental

Wheelz of Hilton Head

Book online
$240.00 - $320.00

description: Golf Cart Rentals! Duration 24 hours Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked...

PB Full Moon Kayak Nature Tour
Book online
$115.00 - $230.00

description: *Explore the Lowcountry waters by the light of the moon!* __________ About A beautiful and serene nature tour, in the moonlight, along the pristine May River. No kayak experience is necessary. _________ Duration 2 hours

Private Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00 - $350.00

duration: 1.75 - 4 Hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from...

SPECIAL / Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$200.00 - $250.00

duration: 1.75 hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. max_age: 1000 group_size: Up to 6 guests accessibility: Two, 8" steps down into...

Wine Blending Class

Kennington Family Winery

Book online
$75.00

duration: 2 Hours min_age: 21 group_size: Maximum 8 Guests description: Blending class- test out different blends of 3 of our Italian wines to determine your favorite ratio. Led by our wine maker or owner, this class will take you behind the scenes...

Afternoon Half Day Sail Trip On Seas the Moment - Our Newest Boat
Book online
$1,203.60 - $1,450.00

duration: 4 Hour cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

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