Hilton Head, SC Vacations

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Featured Vacation Rentals

Dog friendly villa with lagoon views & a...

Summary:Racquet Club Villas 2327The Space:Welcome to Racquet Club Villas 2327, a single-level, dog-friendly condo tucked away in the Harbour Town Area of Sea Pines. This roomy vacation rental overlooks a neighboring lagoon and has freshly been...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunset Rentals | Evian 217

Your dream vacation starts at 217 Evian in Shipyard, Hilton Head Island, SC. This attractively refreshed 3 bedroom, 3 bathroom Shipyard villa will feel like your island-style home-away-from home. This 1,830 sq ft Hilton Head Island villa is...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
2 bedroom/2 bathroom 4th Floor Oceanfron...

Escape to heaven on your Hilton Head Island vacation! Located in the esteemed Hampton Place, in Palmetto Dunes Resort, this oceanfront haven offers an memorable hideaway with one-, two-, and three-bedroom villas. Imagine waking up to handsome...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Fully Renovated Sea Pines Home w Private...

Summary:Oyster Catcher 4The Space:Appreciate your dream vacation in style at this charming home in Hilton Head. Recently refreshed, this getaway features modern furnishings, striking decor, and a impressive full kitchen with stainless steel...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Updated, ground-floor island condo with ...

Summary:Fiddlers Cove 21BThe Space:Island bliss awaits at this ground-floor villa at Fiddler's Cove Beach & Racquet Club. Highlights at your refreshed hideaway include a sleek, updated kitchen fit for feasts, well-appointed furnishings throughout...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Palmetto Dunes condo with shared pool, p...

Summary:Turnberry Village 261The Space:Feel the ultimate island getaway at this opulent 2-bedroom, 2-bathroom condo located near the esteemed George Fazio golf course in Hilton Head, SC. With access to fresh Palmetto Dunes amenities, including a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

3/4 Day Flats Fishing (6 Hrs)

Green Heron Adventures

Book online
$650.00

meeting_point: Beaufort and Hilton Head/Bluffton, SC description: Duration 6 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target...

Sunset Sport Crabbing Adventure

description: Join us for a Sport Crabbing Adventure with a sunset! Duration 2 hours About Our summer night Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on...

Dolphin Tour

Lowcountry Watersports

Book online
$10.00 - $39.99

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours before the activity; no refunds within 48 hours. meeting_point: Palmetto Bay Marina - 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 1 max_age: 99 group_size...

Ocean View

Hilton Head Helicopter Tours

Book online
$39.00

cancellation_summary: Full refund if canceled with at least 24 hours' notice. meeting_point: 38 Gateway circle HHI,SC 29926 accessibility: Stroller and wheelchair accessible description: Get ready for an unforgettable introductory helicopter flight...

Old Town Bluffton Inn May River Discovery Cruise

duration: 90 Minutes meeting_point: 110 Calhoun Street, Calhoun Street Dock group_size: Maximum 6 people pricing: . description: Take a cruise on the May River in an authentic South Carolina skiff boat. Your guide is a master captain and an expert...

Canvas Tote Bag

Historic Mitchelville Freedom Park

Book online
$30.00

pricing: $30 description: Canvas Tote Bag

Creature Feature

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: .75 cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: The Lowcountry is home to an incredible variety of fascinating creatures...

Self-Guided Tours

Historic Mitchelville Freedom Park

duration: 6 Hours description: Discover the rich history of Mitchelville at your own pace with our Self-Guided Tours at Historic Mitchelville Freedom Park This flexible tour option allows you to explore the birthplace of freedom for formerly...

A.C.E. Basin & Monkey Island Tour

Beaufort Dolphin Adventures

Book online
$372.64

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

13 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$95.99 - $191.99

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...

2 Hour Beachcombing Dolphin Tour
Book online
$15.00 - $650.00

duration: 2 hour tour cancellation_summary: All reservations are subject to our 48 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Four Day Bike Rental

Wheelz of Hilton Head

Book online
$43.00 - $86.00

description: Four Day Bike Rental Rates Duration 4 days 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