Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

8 Bedroom/8.5 Bathroom Large Luxurious H...

This roomy 4th row Palmetto Dunes home is the ideal place for a huge family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
Hilton Head Condo: Beach Supplies, Walk ...

Head off to the sugar-white beaches of Hilton Head Island! This 2-bedroom, 2-bath vacation rental in the Fiddler's Cove Beach & Racquet Club features resort-style amenities - like a pool and tennis courts - and proximity to Folly Field Beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Stunning Newly Renovated Condo with Ocea...

Summary:Oceanside Villas II 288The Space:Savor a calming stay at this freshly remodeled, well-maintained ocean view condo in Sea Side Villas. Recent updates include new floor, countertops, backsplash, modernized bathroom, and refreshed interior...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 5
Bright and cheery villa! Close to everyt...

Escape to this delightfully refreshed, top-floor corner villa featuring a wrap-around deck with beautiful vistas. With high ceilings, coastal-inspired colors, and new paint and lighting throughout, this villa is the ideal blend of comfort and...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Charming 2-Bedroom Vacation Rental Overl...

Escape to your ideal hideaway in this gorgeously appointed 2-bedroom Hilton Head vacation rental. Located in a serene setting, this getaway features a private deck that overlooks a lagoon, complete with a relaxing fountain that enhances the relaxing...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Free Tennis & Pickleball, 3 minute Walk ...

*Come Try Us Out Discount* This property is currently 25% off for last-min. reservations for stays in August - September!PROPERTY IS AVAILABLE FOR SHORTER STAYS. 3 NIGHT STAYS!. Any arrival and departure date!!HILTON HEAD ISLAND. This is an...

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

Hilton Head Tours & Activities

Three Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$15.00 - $60.00

duration: 3 day bike rentals cancellation_summary: NO REFUNDS OR RAINCHECKS meeting_point: your address description: Bike rentals for a three day period. (Example: you rent the bikes on monday, they are due back thursday morning) what_is_included...

Beaufort Waterfront

Flip Flop Charters

Book online
$895.00 - $1,025.00

description: Explore Calhoun Street! Enjoy a Small Town Atmosphere! - 4 hours - 5 hours About Take a ride across the Port Royal Sound to the second oldest town in South Carolina. Downtown Beaufort is packed with history, art, shopping and...

Three Hour Beach Combing and Dolphin Nature Watch Tour
Book online
$375.00 - $415.00

description: *Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

Dolphin Cruise

Carolina Breeze Charters

Book online
$275.00 - $350.00

duration: 2 hours meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Discover the best of beautiful Hilton Head Island, SC aboard the Carolina Breeze, a 31-foot yacht-class vessel...

Hilton Head Airport Pickup

Island Head Transportation

Book online
$230.00 - $350.00

duration: 1 Hour group_size: Up to 14 passengers description: Enjoy a seamless and stress-free arrival with our private Hilton Head Airport pickup service. Designed for groups of up to 14 guests, our comfortable transportation includes plenty of...

Facility Tour

Victoria Valley Vineyards at Table Rock

Book online
$15.00

duration: Up to 2 Hours group_size: Max 100 People description: Join us for a tour of our facility and learn more about our small business! The facility tour consists of a 1- to 1.5-hour tour of our winemaking facility and includes a glass of wine. ...

Multi Day Destination sail with Overnight Stay

Anchors Away Sailing Charters

Book online
$1,275.00 - $1,425.00

meeting_point: Hilton Head Island, SC description: *Multi-Day sail to a destination of your choosing* Stay onboard the boat overnight at the dock Duration Up to you!

Firework Cruise

Island Head - Broad Creek

Book online
$39.99 - $599.00

duration: 1.5 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Firework Cruise Take in the sights of the Shelter...

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...

Betty

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. ...

Three Hour Dolphin Strand Feeding Excursion

duration: 3 Hours cancellation_summary: 24 Hours in advance group_size: 12 to 14 description: See dolphins up close! About Dolphin strand feeding is a unique activity of dolphins in the Lowcountry in which a small group of 3 to 5 male dolphins...

Outside DMC Partner Outing - Hilton Head Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

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