Hilton Head, SC Vacations

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Featured Vacation Rentals

Relaxing condo with furnished balcony, o...

HH Beach & Tennis 248COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in Lowcountry coastal leisure at this Hilton Head condo. Soak up the ample South...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Walk to Hilton Head Island Beach: Villa ...

Dive into relaxation at this 2-bedroom, 2.5-bathroom villa on Hilton Head Island! Ideal for snowbirds, this chic coastal vacation rental is located less than a mile from Coligny Beach Park and just a few mins. from golfing, stores, and eateries...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Recently Renovated with Open Concept!  O...

This definitely fantastic villa is located within the Queens Grant Community in Palmetto Dunes. The kitchen was completely remodeled and is now an open concept! All appliances are high-quality stainless steel and the cabinets are bespoke tailored...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Dog-friendly home in Sea Pines with priv...

Planters Wood 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel a true taste of the Lowcountry at this exceptional Hilton Head Island hideaway. Located...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
Idyllic island getaway with pool, privat...

Seascape Villas 3201Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'There is nothing rather like a vacation to the sunshine, pristine golf courses, and white...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
2nd-floor condo with balcony, hot tub, o...

Fiddlers Cove 20FOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering an unbeatable location only a half mile from Folly Field Beach and Folly Field Beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Adventure Camp

Hilton Head Island Recreation Association

Book online
$250.00

duration: 4 days • 3.5 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 30 Campers description: Experience adventure this summer! Participants will make lasting memories of kayaking, stand up paddle...

Donation

Coastal Discovery Museum

Book online
$25.00 - $1,000.00

*Donate Today!*

Seafood Fest Launch and Brunch

Hilton Head Island Recreation Association

Book online
$100.00 - $125.00

duration: 3 hours meeting_point: Rowing and Sailing Center group_size: Up to 25 people description: Island Rec Center is proud to partner with the Hilton Head Island Seafood Festival to bring you a unique kayak and brunch experience! Join us for a...

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Hibachi Dinner Cruise Experience an...

Baby Gear Rental Package • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$220.00 - $280.00

Don't pack it, Rent it! Affordable Baby Gear packages to meet your vacation needs! Duration 7 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Afternoon Harbor Cruise

Seaglass Charters LLC

Book online
$750.00 - $850.00

Come enjoy a couple of hours on the water with us! Duration 2 Hours About This two hour cruise in the harbor will take you to The Battery, The Ravenel Bridge, and out to Ft. Sumpter. A great way to see Charleston from a completely different...

Curator's Tour

Coastal Discovery Museum Hilton Head

Duration 1 Hour About Join us May 6th at 1PM for our final Curator's Tour of our newest exhibit "Binya: Faces ob de Gullah Geechee!" This FREE behind-the-scenes experience is guided by the curators, Elizabeth Greenberg and Angela Dore, as...

Adrenaline Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Crank up the thrill and elevate your helicopter tour to the ultimate adventure with our doorless experience! Soar through breathtaking landscapes with the wind in your hair and unobstructed views that will...

Private Hilton Head Yacht Charter

Hilton Head Boat Charters

Book online
$425.00 - $999.00

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...

Lowcountry Reptiles

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

*The Locals You Haven't Met, Get to Know Your Reptile Neighbors!* ___________________________________ Duration 1 Hour ___________________________________ About This indoor program introduces you to some Lowcountry locals you might not have...

Eco Tour

Hilton Head Helicopter Tours

Book online
$269.00

This amazing flight follows some the most beautiful and remote beaches on the east coast Duration - **30 minutes** About - Along the way you will see shipwrecks, a deserted lighthouse, and old fishing cabins. - This tour also provides a...

Private / Family Shell Hunt & Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75 - $319.00

duration: 1.75 to 2 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. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

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