Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Yacht Club Villas Updated corner condo w...

Summary:Yacht Club 7542The Space:Located in the Palmetto Dunes community, drive 2 miles to the private beach access point or catch an on-demand ride on the courtesy Dunes Buggy. Golfers will savor being less than 3 miles from all three of the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Beautifully remodeled villa with WiFi, i...

Summary:Tennismaster 303The Space:303 Tennismaster is a charmingly modernized, dog-friendly villa overlooking the grounds of the Tennismaster Villas complex. You'll appreciate a private porch and multiple balconies!Tile floors span the entire first...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Freshly Updated Throughout!

Savor the best of Palmetto Dunes Oceanfront Resort on Hilton Head Island from this roomy 3-bedroom, 2.5-bath vacation rental overlooking the resort’s breathtaking 11-mile lagoon system. Set in one of the island’s most sought-after communities...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Peaceful villa with large deck and lagoo...

Summary:Calibogue Club 2617The Space:Located in the serene surroundings of Hilton Head, SC, this striking villa offers calming lagoon vistas from its roomy deck, providing the ideal spot to relax and savor the peaceful ambiance. Just a short walk or...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Luxury 6-Bedroom Family Retreat | Heated...

Welcome to 99 Sandcastle Court, a opulent coastal getaway constructed in 2020, located within the exclusive gated community of Sandcastles by the Sea on Hilton Head Island. Perfectly positioned just a short, breezy walk from the pristine sands of...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Oceanview and Pool view Condo- with beac...

Summary:Shorewood 236The Space:Welcome to your extravagant oceanfront hideaway in Hilton Head, SC! This impressive condo offers charming ocean and pool vistas and is designed for comfort and relaxation. The roomy living room features designer...

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

Hilton Head Tours & Activities

Dolphin Nature Cruise

Island Time Charters

Book online
$325.00 - $399.00

Duration 2 or 3 Hour This is our most popular cruise for a reason! About This Dolphin and Nature Cruise takes you on the waters surrounding Hilton Head Island which inhabit hundreds of Atlantic Bottlenose Dolphins along with, osprey, great...

Private Excursion

Carolina Breeze Charters

Book online
$275.00 - $450.00

duration: 2 to 4 hour options meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Create your perfect day on the water with a custom, private charter aboard the Carolina Breeze, our...

Gift Card

Island Skiff Adventure Tours

One Week Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$41.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

Golden Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

duration: 2 Hours meeting_point: Board Creek Marina 18 Simmons Rd. description: Smooth sailing, stunning views, and something for everyone. Golden Hour Sail is a luxury sunset experience designed for all kinds of groups—families, friends, couples...

Italian Club - Private Sunset Dinner Cruise

duration: 2 Hours meeting_point: Hilton Head Island min_age: 13 description: Hilton Head Italian Club - Sunset Dinner Cruise! **Book online now for fastest and most convenient check out.** *Departing from Harbour Town!* Duration 2...

PVT Shark Tooth 6p

description: Discover Shark Tooth Island! ___ Description Enjoy a boat cruise from Hilton Head Island through the back waterways to Shark Tooth Island (near Savannah, Georgia) where you can hunt for shells, shark teeth and other ocean...

Shrimping

May River Excursions

Book online
$325.00 - $425.00

description: *Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6...

Dolphin & Nature Cruise

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

meeting_point: Broad Creek Marina description: *Opportunity to see bottlenose dolphins, river otters and special species of birds! March through October.* ___________________________________ Duration 1.5...

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...

Kayak Rental: Club Pass Members

Island Head- Hilton Head Harbor

meeting_point: Hilton Head Harbor description: About Welcome to Hilton Head Island’s first Kayak Club! Imagine going for a paddle anytime you want hassle free– no buying, storing, or transporting – just hop in and go. Our kayak membership is...

24-Hour Bike Rental

Wheelz of Hilton Head

Book online
$30.00 - $60.00

description: Full Day Bike Rental Rates Duration 24 hours 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...

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