Hilton Head, SC Vacations

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Featured Vacation Rentals

Pristine Beach Condo with Shared Pools, ...

Summary:Hilton Head Resort 2104The Space:NOTICE: Located close to magnificant eateries, stores, and activities, Hilton Head Resort 2104 is a striking condo that features pond, ocean, and lowcountry marsh vistas. Step into this freshly-furnished...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Large four Bedroom Four Bathroom Home on...

Unwind and relax in your own private getaway, where the pool sits beside the award winning Robert Trent Jones Golf Course. With broad, sweeping vistas, this serene getaway offers the ideal balance of calming solitude and memorable moments. The open...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Dive into Coastal Bliss at our Newly Ren...

This impressive 3 bedroom, 2 bathroom vacation home on Hilton Head Island has been meticulously remodeled to bring the calming essence of the coast indoors. This home sits on a peaceful cul-de-sac and is just short walk to the George Fazio Golf...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Collier, Oceanfront, Dogs OK, Pool, Fr...

2 Collier Beach, Hilton Head Island. Feel luxury living at its best in this elegant oceanfront 5-bedroom, 5.5-bathroom home boasting an oceanfront pool and one of the only pet friendly homes on Singleton Beach. Each bedroom comes with its own...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Coastal condo with balcony, washer dryer...

Summary:Fiddlers Cove 21CThe Space:Follow the sun and end your journey in Hilton Head, a place full of vibrant amusements and happy memories! Right at your stay, be sure to utilize the stellar shared amenities including a heated, outdoor pool, hot...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful Beachside Villa! Oceanfront Po...

Welcome to Ocean Dunes 102!This impressive first-floor condo offers a fresh and modern getaway, freshly repainted and refreshed for your comfort. Featuring one bedroom and one bath, the villa features a new king-sized bed in the master bedroom and a...

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

Hilton Head Tours & Activities

Friday Feeding Frenzy!

Coastal Discovery Museum Hilton Head

Book online
$15.00 - $20.00

description: Duration 1 Hour About TGIF ... even for our animals! Our reptiles, amphibians, fishes, and marine invertebrates all know that Friday means FRIDAY FEEDING FRENZY! Join our animal care staff and learn the ins and outs on how we care...

Private Inshore Charter Fishing aboard Hobo
Book online
$440.00 - $540.00

duration: 3 Hours cancellation_summary: 48 hours meeting_point: Drifter Excursions, 86 Helmsman Way, Palmetto Bay Marina group_size: Licensed for up to 16 passengers; rate includes 6 passengers pricing: - **Two-Hour Charter** - *$440* - Includes 6...

Solaris Charter

Vagabond Cruise

Book online
$395.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate seven to ten passengers...

Learn to Sail Adventure

Otter Sailing Adventures LLC

Book online
$600.00

duration: 3.5 hours or more group_size: maximum of 6 description: Duration 3.5 hours About Experience the thrill of learning to sail on our Catalina 275 Sport, the perfect boat for learning keel boat sailing for the first time or honing your...

Sweetgrass Basket Workshop

Coastal Discovery Museum Hilton Head

Book online
$80.00

description: *Learn traditional basket making from an expert!* ___________________________________ Duration 2 Hours ___________________________________ About Discover the rich tradition of Gullah sweetgrass basket sewing in this hands-on...

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...

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...

4 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours...

Tubing and Dolphin - 16 max

meeting_point: Hilton Head Island description: This 3 hour excursion starts with our most popular Eco trip on pristine Broad Creek. From here We will cross the Calibogue sound into one of our beautiful tidal rivers. Once here we will inflate the...

Family Shell Hunt & Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75 - $269.00

duration: 1.75 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Six Hour Private Offshore Charter
Book online
$1,200.00

max_age: 99 group_size: For up to 6 guests description: Head out from Hilton Head Island for a private fishing charter aboard the Sweet Pea, a 29ft World Cat equipped with modern electronics and tackle. Captain John, a certified and experienced...

PB Charter Fishing
Book online
$895.00 - $1,450.00

description: Description We offer a variety of fishing charters including inshore & near-shore. Our USCG licensed Captains will customize the trip for families and experienced anglers. Our fleet will take you to local hot-spots targeting a variety...

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