Hilton Head, SC Vacations

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Featured Vacation Rentals

Riveting condo home with hot tub, sauna,...

Summary:Hilton Head Resort 4226The Space:NOTICE: The hot water tub is down until further notice. Thank you for understanding.Make this adorable condo your resting spot for your next vacation! Check out Folly Field Beach Park (just a little less than...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Coastal resort-style villa with pool, go...

Plantation Club #446Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'The coastal vacation you've been dreaming of awaits at this Hilton Head Plantation Club...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
7618 Huntington Villas: 3  BR, 3.5  BA V...

Welcome to this elegantly refreshed 3-bedroom townhome located on the spectacular 11-mile lagoon system within Palmetto Dunes Oceanfront Resort. Recently refreshed with new furnishings throughout and a modernized primary bathroom in 2026, this...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Lovely Two Bedroom Villamare Condominium...

Escape to a hideaway in this elegantly appointed two bedroom condominium in the beautiful Villamare community within Palmetto Dunes Oceanfront Resort. This inviting condo offers everything you need for a comfortable and memorable stay.The cavernous...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Courtside Villas Retreat w/pools & tenni...

Courtside 83Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your dream Hilton Head escape awaits at this 2BR/2.5BA townhome! Located in the Courtside Villas...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Ideally located island gem with an outdo...

Summary:Springwood Villas 93The Space:Ideal for a calming hideaway to Hilton Head Island, this two-story condo has all of the amenities of home in a serene package that is sure to spoil you and your guests. The complex is within walking distance to...

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

Hilton Head Tours & Activities

Rosie

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

Seven Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 7 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...

Round Trip Ferry Tickets | 9:30am - 3:30pm | Tuesday - Sunday

meeting_point: 18 Simmons Road, Hilton Head Island, SC description: Round Trip Ferry Tickets to Daufuskie Island for 9:30am - 3:30pm | Tuesday - Sunday Ride the Daufuskie Island Ferry from Broad Creek Marina on Hilton Head Island to Daufuskie...

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton...

Three Hour Inshore Fishing Trip

Hilton Head Island Tours

Book online
$505.00 - $575.00

description: *Three Hour Inshore Fishing Trip* ___________________________________ Rates **Up to Four Guests** - $505.00 **Five Guests** - $555.00 **Six Guests** - $575.00 ***All ages welcome! | Maximum of 1200...

SCM Private SUP Yoga
Book online
$45.00 - $325.00

duration: 1.5 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head Island min_age: 12 group_size: 10 pricing: $225 for up to first 3 people $60 each additional person description: Find your flow where the river meets the sky...

Heritage Garden Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

meeting_point: Meet in front of the Discovery House description: Duration 1 hour and 30 minutes ___________________________________ About All ages welcome but not a Family Friendly program. More geared towards adults but kids that are...

Full Moon Firelight Kayak Paddle

Vintage View River Retreat

Book online
$10.00 - $35.00

description: A 2.5-hour glowing kayak paddle under the full moon, complete with a glow-in-the-dark fun pack and a cozy campfire with treats on the banks of the Pacolet River in Spartanburg South Carolina.

Night Life Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: 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...

Solaris - Destination Charter
Book online
$395.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Customize your luxurious destination charter aboard Solaris today! **Our private charters accommodate up to ten passengers...

One Day Fishing Rod Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **This rental item includes ONLY the fishing pole, reel, and line.** This rental item DOES NOT include TACKLE or BAIT. Tackle and bait...

Sunset Excursion

May River Excursions

Book online
$50.00 - $60.00

description: *One of our most popular trips!* ___________________________________ Rates **Adult** - $50.00 **Child** - $40.00 ___________________________________ Duration 1.5 hours ___________________________________ About - See one of...

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