Hilton Head, SC Vacations

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Featured Vacation Rentals

Top floor vacation rental - expansive oc...

Handsome ocean vistas are just one of the excellent benefits to appreciate from this top floor Hilton Head Island, SC rental. Appreciate broad ocean vistas and you are just steps away from the beach. Sliding door opens to the balcony with ocean...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Beautifully renovated 1 bedroom villa wi...

HH Beach & Tennis 344BOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This gorgeously modernized, 1 bedroom, 1 bathroom condo features impressive ocean...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 5
Ocean Retreat Overlooking the Pool and j...

Welcome to your classy and comfortable 4th-floor getaway, elegantly refreshed for your comfort. This 1-bedroom, 1-bath condo offers serene vistas of the relaxing swimming pool, private tennis courts, and picnic area with a BBQ grille.Inside, you'll...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
DISCOUNTED RATE Aug & Sept. 2026 Beautif...

PERFECT ISLAND GETAWAY FOR FAMILIES AND COUPLES SEEKING A PEACEFUL, BEAUTIFUL AND COMFORTABLE, STREET ENTRY VILLA IN PALMETTO DUNES RESORT. EASY WALK TO BEACH, POOL NEARBY AND CENTRAL LOCATION WITH EASY ACCESS TO ALL ACTIVITIES IN THE RESORT.An...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Welcoming Condo with Lagoon Views, Deck,...

Summary:Beachwalk 142The Space:Beachwalk 142 is a fantastic choice for active travelers, offering painless access to basketball, tennis, and golf right within the community. Guests can also appreciate a roomy on-site swimming pool, and the beach as...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Newly renovated villa near the beach wit...

Forest Beach Villas 100Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Relaxation comes naturally at this tropical hideaway with seamless indoor/outdoor...

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

Hilton Head Tours & Activities

Jet Ski

Lowcountry Watersports

Book online
$159.00

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 description: Experience an exhilarating...

Sunset Cruise

Island Time Charters

Book online
$350.00 - $450.00

The most spectacular views and vivid colors! Duration 2 or 3 Hours About This Sunset Cruise allows access to the best locations in the Low Country to enjoy the breathtaking views. With the sunset on one side of the boat and a view of the...

Pride on the Pacolet

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Come celebrate Pride Month and light up your weekend! Glide down the river with glowing rainbow gear, good vibes, and nonstop Saturday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with...

Lowcountry Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if weather forces cancellation and no mutually available reschedule; otherwise weather-dependent rescheduling. meeting_point: Jarvis Creek Park, 100 Jarvis Park Rd, Hilton Head Island...

Kids Summer Splatter-Paint Camps

Color Me Greenville

Book online
$225.00

duration: 30 mins meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: Kids Summer Splatter-Paint Camps

Three Day Electric Bike Rental

duration: 3 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Solaris - Sandbar Sunbathing Charter

duration: 3.5 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book a luxurious charter aboard Solaris to the Sandbar only accessable by boat! Escape to paradise with our exclusive...

PB 7 Hour Ultimate Lowcountry Day
Book online
$110.00 - $1,565.00

description: *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...

Public Afternoon Sail on Knot The Office

Anchors Away Sailing Charters

Book online
$95.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Minimum of 4 - Maximum of 6 people accessibility: Limited Handicap accessibility, Please call us...

Five Hour Private Nearshore Charter

max_age: 99 group_size: For up to 6 guests description: Fish the productive waters around Hilton Head Island with Captain John aboard the Sweet Pea, a fully equipped 29 ft. World Cat. Depending on the season, your trip may target cobia, bull...

Native Plant Sale

Coastal Discovery Museum Hilton Head

description: Come and join us for the next Coastal Discovery Museum annual Native Plant Sale in October 4th from 10 am - 1 pm. The sale will take place at the Coastal Discovery Museum on the Honey Horn grounds. Over 90 species of native plants will...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$500.00 - $600.00

description: Fish like a local! Duration 3 Hours About Targeting Red Drum, Black Drum, Seatrout, Flounder, and Sheepshead in local tidal creeks and nearby waterways with light tackle. This trip is great for all experience levels! 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