Hilton Head, SC Vacations

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Featured Vacation Rentals

Spectacular Harbourfront Villa completel...

HILTON HEAD ISLAND. Main Sail – a extravagant villa complex on Hilton Head Island overlooking Shelter Cove Marina in Palmetto Dunes resort. Each villa features water vistas from nearly every room, screened porch, two master suites, and many...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Stunning Newly Renovated Condo w/ Ocean ...

Sea Side Villas II 288Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This newly remodeled condo in the Sea Side Villas complex is just what you need to have...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 5
2 Bedroom Luxury Villa

Welcome to this elegantly remodeled single-level villa offering 2 bedrooms and 2 full bathrooms, thoughtfully designed for comfort and relaxation. As you enter, you’ll be greeted by a gorgeous, entirely refreshed kitchen featuring quartz...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Marriotts Barony Beach Club - 2 Bedroom

*** Sanitation/Cleaning Update ***Over the next few months, when guests are in hotels within the Marriott portfolio, they will notice a number of additions to our cleaning regimen designed to set an even higher standard of cleanliness for the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
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
Bright & Beachy Dog-Friendly Villa w/ Fa...

Tennismaster 1102Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

SC Pimento Cheese Festival - Tasting Ticket

A festival to showcase South Carolina's Favorite snack, Pimento Cheese Rates General Admission is Free and $5 Parking Fee per car at Gate Tasting Tickets are **$5 per person** Each Tasting Ticket holder will receive 6 tasting tickets to sample...

Four Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$645.00 - $935.00

Golf Cart Rentals! Duration 4 days 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 online due to South...

Three Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

Enjoy miles and miles of scenic bike paths Duration 3 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

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...

Intro to Stand Up Paddleboarding

duration: 1.5 Hours meeting_point: Hilton Head Island, SC pricing: description: *Stand-Up Paddleboarding is easy to learn, a fantastic workout, and lots of fun!* Launch your Stand-Up Paddle Boarding career with this intro to SUP lesson in...

PB 5 Hour Ultimate Lowcountry Day
Book online
$87.50 - $1,175.00

*Customized adventures are the best way to see and do the Lowcountry!* Description Designed for the family or small group interested in experiencing an authentic day in coastal Carolina. We will give you a menu of options that can include...

Two Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$35.00 - $120.00

Electric Bike Rental Duration 2 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Fishing Charter - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

Duration 3 to 8 Hours Options About Near-Shore and Off-Shore Fishing. Ultra Stable, lots of shade, bean bags and Best of all Super Lucky! This experience is perfect for going after anything and possibly catching Bull-REDFISH, SEA TROUT...

Night Life Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

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 individuals...

The Spirit of Whiskey

Hilton Head Distillery

Book online
$95.00

Whiskey has deep Irish roots, and around the time of St. Patrick's Day, this cocktail class is a great excuse to explore what makes whiskey such a versatile spirit behind the bar. In this hands-on class, you’ll mix, sip, and learn your way...

Beach Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

duration: 14 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Hilton Head Seafood Festival: Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Lowcountry Boil Dinner Cruise aboard The Ohana Step aboard The Ohana, Outside Hilton Head’s stunning luxury...

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