Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Oceanfront Palmetto Dunes condo with ama...

Summary:Barrington Court 409The Space:Feel the beauty of Hilton Head Island from this completely remodeled one-bedroom condo offering striking ocean vistas. This dog-friendly home, located in Barrington Court, is surrounded by lush horticultural...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Family Friendly Villa near the Beach wit...

Summary:Fiddlers Cove 2JThe Space:Make your vacation ideal with an island hideaway in the Fiddlers Cove Complex. This two-bedroom, two-bathroom getaway offers a comfortable calming environment to spend your vacation right on Hilton Head Island. The...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Gorgeous and sunny home with pool, beach...

Summary:Kingston Dunes 68The Space:Cavernous, and private, the ideal Hilton Head Island hideaway exists, and it's here! This secluded home is against the backdrop of handsome Spanish moss trees with a private pool, sun deck, and is only a short...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beachfront escape with pools, hot tub, W...

Summary:Island Club 2103The Space:Escape to the beach at this charmingly located ground-floor, oceanfront condo in the calming, 27-acre Island Club on Hilton Head Island. Ideal for a calming coastal hideaway, this beautiful getaway offers the ideal...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Bright & Beachy Dog Friendly Villa with ...

Summary:Tennismaster 1102The Space:Recently refreshed from top-to-bottom, this charming, two-story townhouse features all-new floor, lighting, cabinets, countertops, appliances, and furnishings to ensure the ultimate comfort for your next hideaway...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Professionally decorated townhome with m...

Summary:Harbour Town Club Villas 1253The Space:1253 Harbour Town Club is a highly desired, professionally decorated, multi-level townhome right in the heart of Harbour Town in Sea Pines Plantation. This pretty escape is ideal for all looking to real...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 9

Hilton Head Tours & Activities

Two Week Electric Bike Rental
Book online
$475.00

duration: 14 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Lowcountry Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if weather forces cancellation and no mutually available reschedule; otherwise weather-dependent rescheduling. meeting_point: Jarvis Creek Park, 100 Jarvis Park Rd, Hilton Head Island...

Three Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$140.99 - $281.99

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...

Beach Gear Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

duration: 14 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

description: Come and discover the Hidden, but not Forgotten Treasures of Historic Bluffton. Duration 45 Minutes About We will discover long lost Hidden Treasures in and around Beautiful Old Town Bluffton. More info There is a 4 person...

Dolphin Eco Tour

Captain Moto Adventures

Book online
$325.00

description: Duration 2 Hours About Not just your everyday dolphin tour. This is a private tour for the family. Learn about the local ego system and see dolphins. What to bring - BYOB - Sunglass - Sunscreen *No spray lotion* ...

PB Charter Fishing
Book online
$895.00 - $1,450.00

description: Description We offer a variety of fishing charters including inshore & near-shore. Our USCG licensed Captains will customize the trip for families and experienced anglers. Our fleet will take you to local hot-spots targeting a variety...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

description: Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only...

Beach Bum

Hilton Head Helicopter Tours

Book online
$109.00

duration: 20 miles description: This helicopter tour follows Hilton Head’s most active stretch of beaches to Coligny Beach, the island’s popular beach park. Pilots keep the flight low along the shoreline for close-up views of surf and potential...

PVT Dolphin Eco 6p

description: *Our Most Popular Boat Trip!* --- Description Explore the marsh and search for the infamous Atlantic Bottlenose Dolphin... Join us for a tour on Broad Creek watching for birds and dolphins in the salt marsh ecosystem. Explore...

Vineyard Tour

Victoria Valley Vineyards at Table Rock

Book online
$50.00

duration: Up to 2 Hours group_size: Max 4 People description: Join us for a tour of our vineyard and learn more about our small business! The vineyard tour consists of a 1- to 1.5-hour tour of the vines on our 47 acre property, where you’ll...

Private Party

Palmetto Axes

description: Get the joint all to Yourself! About *Ages 12+ • Up to 36 People* All the fun for you and as many people as the fire marshal will let in the place. Book 2 plus hours and save even more! - Bring in your own food - Maximum of 36...

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