Hilton Head, SC Vacations

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Luxurious home with private pool, centra...

Surf ScoterOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Surf Scoter offers luxury vacation rental at its best! This striking multi-level home, located just...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Charming Oceanfront Retreat, Steps from ...

The villas at Beachwood Place are expertly managed by Vacation Time of Hilton Head and are best reserved directly through our website.This second-floor oceanfront villa on South Forest Beach Drive features two bedrooms, two bathrooms, and a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Dog-friendly villa with pool, beach acce...

Island House 131Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover white sandy beaches, fantastic golfing options, and pretty greenery at this...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Ocean View , Top Floor, 6502 with roof, ...

Feel the tranquility of oceanside living in this meticulously appointed two-bedroom villa, boasting an awe-inspiring ocean panorama. Whether from the master bedroom, roomy living area with new furnishings, or the broad top-floor balcony complete...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
507 Barrington Arms ~ 5th Floor Ocean Vi...

Barrington Oceanfront Complex | Just steps from the Beach ***Please be advised that the Pool, Hot Tub, and Grilling Area will be closed for required repairs starting November 3, 2025, with work expected to be finished by the end of January 2026.*2...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
The best for less at the Hilton Head

Located on Hilton Head Island, this resort is just 2 blocks from the beach and features 2 outdoor pools, a hot tub, and a kids’s area. Free WiFi is available. Condos at Waterside Resort by Spinnaker feature a private balcony. They have a full...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Raffle - 2025 Sweetgrass Basket

Coastal Discovery Museum

Book online
$10.00

duration: 1/6/2025 - 1/31/2025 meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC 29926 pricing: $10 each description: Coastal Discovery Museum's Sweetgrass Basket raffle to be drawn at the 2025 Cocktails & Camellias event at 7:30 p.m. on...

Lake Keowee - Jet Ski Rental

Captain Cams Watersports

Book online
$275.00 - $350.00

duration: 4-7 Hours meeting_point: 470 Green Pond Rd, Anderson, SC 29625 min_age: 25 group_size: Up to 6 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight of the...

After School Skate Club

Hilton Head Island Recreation Association

Book online
$100.00 - $600.00

duration: 4 Weeks • 1 Day Per Week • 2 Hours Each Day meeting_point: Island Recreation Center min_age: 7 max_age: 18 group_size: Up to 20 Campers description: Learn from one of the best and most experienced instructors on Hilton Head at the...

Six Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$800.00

Duration 6 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, Cobia, Sharks! 6hrs gives us time to target a couple different species, more fishing time, more spots...

Kayak Tour of Jarvis Creek

Coastal Discovery Museum Hilton Head

Book online
$36.00 - $40.00

*Look for for bottle-nosed dolphins, wading birds and other local wildlife!* ___________________________________ Duration 2 Hours (including safety training and launch) ___________________________________ About Join a naturalist guide in a...

Two Day Double Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$45.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Private Full Day Cruise

Unwritten Charters LLC

Book online
$1,500.00

Come enjoy a couple of hours on the water with us! Duration 6 Hours About This Full Day 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...

Pumpkin Painting Session

Color Me Greenville

Book online
$30.00

duration: 60 minutes meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: This fun event is a must for Girls Night Out! You will get a 6” faux pumpkin to paint in your own color scheme and style. We can show you some examples of...

Go Try Archery

Hilton Head Island Recreation Association

Book online
$30.00

duration: 2 Hours meeting_point: Mid-Island Tract group_size: Up to 30 people description: Take aim at Hilton Head's first-ever Try Archery Event! Outdoor Rec's USA Archery certified instructors will provide you with basic instructions to try...

Two Day Beach Cornhole

Hilton Head Outfitters - Bike Rental

Book online
$55.00

PORTABLE CORNHOLE SET – This tailgating game includes 2 portable cornhole boards (2x3 feet), 8 all-weather regulation bean bags, and cornhole Rules. For travel, tailgating, beach, lawn, or backyard WATER FILLED - Lightweight travel cornhole boards...

Two Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$380.00

Duration 2 Hours ___________________________________ About Learn about fishing, catch sharks and other species and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you will catch....

Crabbing

May River Excursions

Book online
$300.00

*Our most interactive and famous excursion!* ___________________________________ Rates **Private Charter** - $300 for 6 people or less. *(Can hold up to 12 people for extra charge, call for more...

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