Hilton Head, SC Vacations

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Featured Vacation Rentals

Family-Friendly Home w/Private Pool, Scr...

Gloucester 36Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Marriott Sunset Pointe, 2025 PGA Tour RB...

Great location for RBC Heritage week-April 14-21. Full week rental.Check is at 4 PM, check in at the resort as if booked through Marriott. All resort services and amenities supplied. Free parking.The villas are roomy, with entirely equipped kitchen...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Coastal condo- close to Coligny Plaza, B...

Surf Court #80Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel modern comfort and convenience at this updated two-bedroom, two-and-a-half-bath beach condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunning home- lagoon views and close to...

Serene SpartinaOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of the esteemed Sea Pines Resort in Hilton Head, SC, this roomy home...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
You are going to love this completely re...

Savor this completely refreshed one level villa with pretty vistas of the George Fazio Golf Course!Invite your friends over and appreciate watching your favorite show with plenty of seating in the living room or relish in a card game on the outside...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Large Two Bedroom Villa Located Steps Fr...

Treat yourself to this huge two bedroom and three bathroom villa located mere steps away from the pool located in the Water Oak community within Palmetto Dunes! The first floor consists of the primary suite, bathroom, living, dining, and kitchen...

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

Hilton Head Tours & Activities

Ocean View

Hilton Head Helicopter Tours

Book online
$39.00

This introductory tour offers views of Folly Field Beach and the Port Royal Sound. Duration - **3 minutes** About - This tour offers great views of Folly Field Beach, Broad Creek, Port Royal Sound, and Shelter Cove.

Three Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$45.99 - $91.99

Three Day Rental Rates: - 16” Kids Beach Bike: $45.99 - 20” Kids Beach Bike $45.99 - 24” Youth Beach Bike: $45.99 - 26” Bike w/ Child Seat: $60.99 - 26” Mens Beach Bike: $45.99 - 26” Unisex Beach Bike: $45.99 - 12" Balance Bike...

Sweetgrass Basket 3-Day Workshop

Coastal Discovery Museum Hilton Head

Book online
$425.00

March 19, 20, 21, 2025 from 9:30-12:30 on each date. World-famous but with origins right here in the Lowcountry, the Sweetgrass basket is one of the region’s best known art forms and cultural icons. Learn about the history of sweetgrass basket...

Corporate Parties & Team Building

Color Me Greenville

Book online
$50.00 - $350.00

duration: 1.5 Hours cancellation_summary: 7 Days meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: 1.5 hours active painting for groups of people. Includes a 11”x14” premium canvas for each attendant plus a 18”x24”...

Shared / Fireworks & Guaranteed Dolphin

Dolphin Discoveries Hilton Head

Book online
$69.75

duration: 3 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

One Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$29.99 - $39.99

The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

Columbia's Shrimp & Grits Fest

Columbia's Shrimp and Grits Fest

Book online
$25.00 - $75.00

Columbia's Shrimp & Grits Fest >On Saturday, June 21st, 2025 area restaurants will compete in Columbia's 10th Shrimp & Grits Fest. One restaurant will be named "Columbia's Best Shrimp & Grits" by a panel of judges. There will also be a winner in...

Learn to Row

Hilton Head Island Recreation Association

Book online
$40.00

duration: 2 days • 3 hours per Day meeting_point: Rowing and Sailing Center min_age: 11 max_age: 18 group_size: Up to 10 Campers description: Learn the basics of rowing. The camp utilizes 1-4 person shells (boats) and will teach participants...

Bike Rental • Four Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Rent Bikes and Gear Accessories for your vacation! Duration 4 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Morning Segway and Coffee
Book online
$115.00

Start your day on a caffeinated Segway ride! Duration 1.5 Hours About 50% Segway. 50% Coffee. 100% Fun! Join us for this fun & unique way to explore Hilton Head Island! This 2.5 hour tour will be one of the highlights of your vacation...

New Sailboat Seas The Moment - 2-hour Afternoon Sail and dolphin watch

*Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with handling sails if you desire, but either way, kick back...

Sweet Surprise Treat Tour- Feb 18 - March 4

Ticket is valid: Saturday, February 18 - March 4 Receive 7 treats within 14 days Exchange your coupons (PDF will be sent via email and will need to be printed out) for a treat at each sweet shop. The Midlands has some delicious dessert shops...

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