Hilton Head, SC Vacations

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Featured Vacation Rentals

Ocean View Condo Steps From Hilton Head ...

Summary:Savor a calming Hilton Head Island hideaway at Ocean Villas C219, a comfortable 1-bedroom, 1-bathroom condo that sleeps up to 6 guests. The home features a queen bed in the bedroom, a sleeper couch in the living room, and constructed-in...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Second-Floor Condo with WiFi, Pool, Golf...

Summary:Plantation Club 431The Space:This villa has a view of the Sea Pines' Heron Point Golf Course, a jetted tub, and access to the complex's shared pool. These amenities make it a great choice for active families who appreciate to golf, bicycle...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Condo 1 block from Coligny Plaza with on...

Summary:Sands Village A2CThe Space:Located in the heart of Hilton Head, SC, this striking villa is just blocks away from the pristine beaches of the island. Located only one block from Coligny Plaza, the vibrant hub of the area, you'll have painless...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 5
Golf Course Adjacent Villa with Fast WiF...

Summary:Waterford B1The Space:Find your way to the fairway at this chic and sunlit vacation rental on Hilton Head Island! Classy and fashonable throughout, this gorgeous, two-story, family-friendly home features a well-equipped, full kitchen with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Fully Updated Kitchen and Bathrooms with...

As you enter this villa you are greeted by the open concept Kitchen, Dining and Living Areas. The Kitchen has been refreshed with tiled countertops, stainless steel appliances and bespoke cabinetry. The Dining Area has seating for six. The Living...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Sun-kissed bliss at Colonnade Club with ...

Summary:Colonnade Club 158The Space:Appreciate sun-kissed mornings on the private deck when you choose this bright and cheery condo as your home base on the island. Complete with golf course vistas and a completely remodeled interior, this roomy...

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

Hilton Head Tours & Activities

Dolphin Tour

Island Head - Broad Creek

Book online
$10.00 - $499.00

duration: 90 Minutes cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: See Dolphins up Close! Join us...

Old Town Bluffton

Hilton Head Helicopter Tours

Book online
$229.00

max_age: 100 description: Experience an exhilarating helicopter tour over Hilton Head and Bluffton that highlights the area's natural beauty and historic sites. Fly over Pinckney Island to look for bald eagles and hawks, sweep across Bluffton’s...

Luxury Sunset Cruise

BC2 - Island Head

Book online
$1,200.00 - $1,600.00

duration: 2-6 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Revolutionary War Lecture Series

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: 1 hour cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. min_age: 13 group_size: 60 description: Join us for "Revolutionary Reflections", a...

Sunset Fireworks Sail

Salt Marsh Sailing

Book online
$479.00 - $599.00

description: *Watch the show from the boat!* ___________________________________ Rates **Private Charter (Up to 6 People):** $479 ___________________________________ Duration 2.5 hours ___________________________________ About It’s a...

Hourly Kayak Rentals

Crooked Creek Kayaks

Book online
$15.00 - $100.00

duration: 1 - 4 Hours description: Unguided access begins with personalized, concierge-style recommendations designed to help you move with Jarvis Creek’s ever-changing tidal currents. Before you launch, our team will walk you through ideal...

Family Golf Class

Palmetto Dunes Golf Academy

Book online
$1,690.00

description: Duration & Rates - Three days, two hours of private lessons daily - $1,690 per family About The Family Golf School is a custom program of golf instruction designed to fit a family's needs and skill level. The schedule is flexible...

Pontoon Boat Rental

Lowcountry Watersports

Book online
$270.00 - $625.00

duration: 2 Hour, 3 Hour, 4 Hour or 6 Hour cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 group_size: **Maximum of 10...

13 Day Rental

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Weekday 9:30am-3:30pm Golf Cart Rental
Book online
$70.00 - $90.00

description: Weekday - Golf Cart Rental 9:30am - 3:30pm *Must have valid Driver's License to rent a cart.*

Afternoon Half Day Sail Trip On Seas the Moment - Our Newest Boat
Book online
$1,203.60 - $1,450.00

duration: 4 Hour cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

Cruise Through The Stars

Vagabond Cruise

Book online
$19.95 - $39.95

duration: 1.5 Hour meeting_point: 149 Lighthouse Rd. Hilton Head Island, SC 29928 accessibility: Stroller and wheelchair accessible on the lower deck of the Vagabond description: ![Description of...

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