Hilton Head, SC Vacations

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Featured Vacation Rentals

Secluded home & pool house with private ...

Summary:Whistling Swan 3The Space:You don't have to compromise any sense of home at this gorgeous island getaway. Surrounded by lush foliage with fast access to the beach, you will have no trouble settling in and slipping right into vacation mode...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Peaceful 1st Floor Lagoon View - Monthly...

Welcome to CORAL REEF RETREAT—your calming oceanside hideaway where every moment feels kissed by sunshine and sea breeze. Tucked away on the first floor of Ocean Villa C at Hilton Head Island Beach & Tennis Resort, this cozily designed one-bedroom...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Corner unit townhome with lots of light ...

This dazzling, freshly refreshed townhome is conveniently located on the George Fazio Golf Course in Palmetto Dunes - just a short walk to the beach! This 2-bedroom end-unit villa in Palmetto Dune’s Turnberry Village has been thoughtfully...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Stunning 3rd Floor Ocean View - Monthly ...

Welcome to OCEAN LINKS — your breezy island hideaway tucked inside the beloved Hilton Head Resort! Perched on the 3rd floor of Building #2, this newly designed two-bedroom, two-bath getaway blends coastal comfort with laid-back luxury — the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Island Club Villa | Ocean Views & Beach ...

Summary:Welcome to the Sandpiper Villa! ???? Ocean-View Island Club Villa | Feel the Ocean Breeze!The Space:Welcome to Island Club 1306—your calming 2BR/2BA getaway in the sought-after Island Club resort. This bright and airy 3rd-floor end unit...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Waterfront resort on PR Sound!

Fall 2025 refresh! Kick back and relax with family and friends in this well appointed, fresh villa. Carefully curated furnishings, linens, and linens to give you an fresh vacation experience! Far from the traditional rental space - pride of...

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

Hilton Head Tours & Activities

Blue Granite Express

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Guests enjoy a narrated 90-minute trip through Fairfield County countryside. Seating on the train is on board an open-air car, allowing easy viewing as...

Sunset Cruise

Flip Flop Charters

Book online
$595.00

description: Breathtaking sunsets! Duration 2 hours About Join us for a 2 hour cruise through the intracoastal to take in Hilton Head’s breathtaking sunsets. There’s no better place to take in the beauty of the sun setting over the...

Private Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00 - $350.00

duration: 1.75 - 4 Hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from...

Beaufort Lands End Paddling

Book online
$40.00 - $60.00

duration: 1.5-2 hours meeting_point: Russ Point Boat Landing, Sea Island Pkwy & Fripp Island Bridge (across from Nature Center) description: Join us for a one-of-a-kind kayak adventure, perfectly timed with the high-tide, offering exclusive access...

Life Under the Sea

Coastal Discovery Museum Hilton Head

Book online
$5.00

description: There is a magical world full of fascinating creatures under the sea! Join knowledgeable Museum staff and volunteers in the Discovery Lab to explore, touch, create, play, and learn more about ocean life. Who lives in those shells? What...

Music with Friends Ohana Cruise to Southern Raised Concert

meeting_point: 41 Boathouse Street, Bluffton SC 29910 description: Join us for a complimentary round-trip cruise aboard the Ohana on Monday, June 1, for Music with Friends on the Bluff. Guests will meet and check in at the Outside Palmetto Bluff...

One Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$34.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Umbrellas include a sand spike for easy set up at the beach. The durable and comfortable reclining Hilton Head Outfitters beach chair...

Jet Ski Creek Run Tour

Lowcountry Watersports

Book online
$199.00

duration: 2 hours cancellation_summary: Cancellations allowed up to 48 hours prior to the scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 max_age: 99 description: Get ready for...

Three Hour Dolphin Strand Feeding Search

Hilton Head Island Tours

Book online
$375.00 - $395.00

description: *Dolphin Strand Feeding is a unique and exciting behavior developed by local Atlantic Bottlenose Dolphins!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** ...

Wonderful Wings

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $25.00

description: *Get up close and personal with local butterflies!* ___________________________________ Rates - **$6 per adult, $6 per child (Geared to preschool age & younger children, but fun for the whole family!) - **3 and under, no...

Kids Story Time

Coastal Discovery Museum Hilton Head

meeting_point: 70 Honey Horn Drive, Hilton Head Island, SC description: Look, listen, and learn! Kids will love hearing local stories and learning about Lowcountry wildlife and history. Stories are geared towards preschool and lower elementary aged...

Two Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$110.00 - $262.00

description: Enjoy miles and miles of scenic bike paths Duration 2 Weeks About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals - please select during...

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