Hilton Head, SC Vacations

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Featured Vacation Rentals

2-Bedroom 2.5-Bathroom villa located on ...

Savor a calming Hilton Head Island hideaway in this 2-bedroom, 2.5-bathroom villa located in the Water Oak community within Palmetto Dunes Oceanfront Resort. With a roomy layout, private outdoor areas, and convenient access to the community pool...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Large Three Bedroom and Three Bathroom V...

This Fazio villa will be ideal for your next vacation hideaway! With ample room, three bedrooms and three bathrooms and updates throughout, what's not to appreciate? The kitchen is handsome featuring granite countertops, stainless steel appliances...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Beautifully renovated villa with stunnin...

Welcome to heaven! This freshly refreshed two bedroom, plus additional room, two bathroom villa is a ideal place to stay on your Hilton Head vacation. Its calming and coastal feel has impressive expansive vistas of the George Fazio golf course and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Welcome to Your Perfect Hilton Head Geta...

Welcome to Your Ideal Hilton Head Getaway!This roomy 4-bedroom home is designed for comfort and relaxation, making it the ideal spot for your next vacation. Located in a prime area, the open-concept layout provides plenty of room for everybody to...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Heated Oceanfront Pool!  Oceanside with ...

Welcome to Ocean Dunes 101!! Where coastal appeal meets comfort. The Ocean Dunes complex is an oceanfront gem, located just 70 yards from the beach. This gorgeously decorated villa features two bedrooms and two bathrooms, designed to make your stay...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Recently Renovated Coastal Inspired Vill...

Immerse yourself in tranquility at this beautiful, one-level villa. Totally refreshed and decorated in serene colors, the space exudes a sense of calm, the ideal escape for a calming hideaway. The entirely equipped kitchen accepts you to whip up...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5

Hilton Head Tours & Activities

Sallie Ann Authentic Gullah Tour

Daufuskie Island Gullah Heritage Society

Book online
$70.00

meeting_point: Daufuskie Island, SC description: See and enjoy a Gullah Tour on Daufuskie through the eyes and memories of a sixth generation Gullah native! Duration 3 Hours About We are a non-profit organization. Take a relaxing boat ride...

Guided Wine Tasting

Victoria Valley Vineyards at Table Rock

Book online
$28.00

duration: 90 Minutes min_age: 21 group_size: Max 15 People description: Come taste a little piece of Europe with a traditional wine tasting of our European Vinifera wines, sure to be enjoyed by any wine drinker from a novice to the connoisseur. Your...

Hilton Head Plantation Kayak Club May River Kayak Tour

meeting_point: Outside Palmetto Bluff

2026 Juneteenth Arts, Crafts & Prepared Food Vendors Registration

duration: June 13th from 10am-4pm description: We invite local artists, crafters, food vendors, and nonprofit organizations to join us for a day of culture, history, and community at the 12th Annual Juneteenth Celebration! This is a great...

Banana Boat Rides

H2O Sports

Book online
$39.00

duration: 20 Minutes min_age: 6 description: Come enjoy an exhilarating ride aboard the 6 passenger, double-sided banana boat. Duration 20 Minutes About The journey begins in Harbour Town as you load up on the banana boat and steady yourself...

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...

Lowcountry Marsh Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if reschedule cannot be arranged. meeting_point: 59 Shelter Cove Lane, Hilton Head Island, SC description: Join us along the Lowcountry...

Old Town Bluffton

Hilton Head Helicopter Tours

Book online
$229.00

max_age: 100 description: Experience an exhilarating helicopter tour over Hilton Head and Bluffton that highlights the area's natural beauty and historic sites. Fly over Pinckney Island to look for bald eagles and hawks, sweep across Bluffton’s...

Art Market: Fine Art and Craft Festival Tickets

Coastal Discovery Museum Hilton Head

Book online
$5.00

meeting_point: Coastal Discovery Museum at Honey Horn description: $5 per adult, FREE for ages 12 and under Original art for sale Food and drink available for purchase Advance tickets are not required, but only cash will be accepted for...

Hilton Head Dolphin Tours (2 Hours)

Hilton Head Boat Charters

Book online
$340.00 - $799.00

duration: 2 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 group_size: Up to 20 People description: The best 2-hour charter on the island Ride in...

Sunset Mini Boat Dolphin Tour

Lowcountry Watersports

Book online
$249.00

duration: 2 hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 5 group_size: 2, 3, or 4 per mini...

CFT Merchandise

Columbia Food Tours

Book online
$2.00 - $30.00

meeting_point: Columbia, SC description: We have products we'd love to share with you to help you remember the great time you had on our Columbia Food Tour.

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