Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront luxury, ocean and pool views,...

At a Glance• Status: Totally refreshed (Completed Feb 2026)• View: Direct Oceanfront (Windsor Court)• Sleeping: King Suite + Premium Queen Sleeper Couch• Access: Effortless access to pool, beach path, and fire pits• Location: Heart of...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Hilton Head Vacation Rental steps away f...

This enormous three bedroom and three bathroom villa overlooks the pool and is seconds from the beach! Upon entering the home there are two bedrooms on the first floor. The left bedroom features two Queen-sized beds and an en-suite bathroom with...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Gorgeous new luxury beach house - be the...

This new, 5 bedroom, 5 ½ bath, home is a ideal fit for extended families, or as a multi-family vacation residence. Feel absolute luxury and convenience in this beautiful professionally decorated coastal beach home. As a guest at Serenity Now you...

  • Hilton Head
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
Significant Golf Views from this 3-Bedro...

Welcome to this handsomely maintained 3 bedroom, 3 bathroom townhouse style villa located in the sought after Fazio Villas within Palmetto Dunes Oceanfront Resort. Decorated with coastal inspired furnishings, this corner villa offers a ideal blend...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Spacious waterview haven with decks, fir...

Sound Villas 1452Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A roomy haven in the Sound Villas community, this family-friendly home is a sure bet for a...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15
Spacious Palmetto Dunes Condo, Sunny Dec...

Queens Grant 792Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene hideaway in Hilton Head, SC! This roomy Palmetto Dunes condo offers a...

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

Hilton Head Tours & Activities

Volunteer Open House

Coastal Discovery Museum Hilton Head

meeting_point: Coastal Discvoery Museum description: Help inspire people to care for the Lowcountry. Adults (18+) are invited to explore how they can contribute their time and talents to support the museum’s mission and foster community...

Nine Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$75.99 - $151.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Two Hour Dolphin Nature Cruise

Hilton Head Island Tours

Book online
$250.00

description: *Enjoy your 2 Hour Dolphin Nature Cruise!* ___________________________________ Rates **Private Charter** - $250.00 ***All ages welcome! | Maximum of 1200 lbs*** ___________________________________ About your Fishing Trip: ...

2026 Juneteenth Non-Profit  Registration

Historic Mitchelville Freedom Park

duration: June 13th from 10am- 4:00pm description: **Non-profit no selling of items** 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...

Hilton Head Plantation Kayak Club May River Kayak Tour

meeting_point: Outside Palmetto Bluff

The Art of Tiki Cocktail Class

Hilton Head Distillery

Book online
$95.00

duration: 2 meeting_point: Hilton Head Distillery min_age: 21 group_size: Maximum 12 description: Join us at Hilton Head Distillery for an unforgettable hands-on experience where you'll shake, stir, and garnish your way through the colorful world of...

2 Hour Wambaw Creek Wilderness Area Blackwater Tour
Book online
$55.00 - $110.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Full Moon Glow Bike Tour

Glow Bikes Hilton Head

Book online
$41.00 - $50.00

description: Experience the enchantment of our Full Moon bike tour on glowing bicycles! Overview Unique moonlit tour on glowing bicycles 3 picturesque stops at Hilton Head Island landmarks Perfect for individuals, couples, families, and...

Two Week Bike Rental

Wheelz of Hilton Head

Book online
$85.00 - $170.00

description: Two Week Bike Rental Rates Duration 14 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Two Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$63.99 - $79.99

description: Single Kayak 2 Hour Rental: $53.99 ________________________________ Double Kayaks or Canoes 2 Hour Rental: $66.99 __________ Triple Canoe 2 Hour Rental: $79.99

Six Oaks Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head setting...

Sip & Sunset - BYOB Adults Only Dolphin Cruise

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 21 max_age: 99 accessibility: Boat is...

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