Hilton Head, SC Vacations

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Featured Vacation Rentals

Family-Friendly Townhome with Lagoon Vie...

Summary:Island Club 108The Space:Located near a lagoon in the Island Club on Hilton Head, this family-friendly suite offers access to a shared pool and hot tub to help you relax. After spending hours roaming the beach and surrounding area, you can...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Pool, Spa & Dining: Beach Condo in Hilto...

Book an memorable trip to this 1-bedroom, 1-bathroom vacation rental condo on Hilton Head Island and soak up some southern sunshine. With access to a community pool, on-site restaurant, tennis courts, and more, this Hilton Head Beach & Tennis Resort...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Newly Renovated Villa at The Spa on Port...

Summary:Spa on Port Royal Sound 3121The Space:Don't miss out on this hidden treasure! Located in The Spa on Port Royal Sound, this freshly modernized 2BR villa features a secluded, gated setting with private access to one of the quietest beaches on...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunset Rentals | Evian 190 | Dog Friendl...

This 2 bedroom, 2.5 bath townhouse villa offers both a golf and nature view. The living room beckons with a sizable couch, 2 upsized chairs one which folds out into a twin couch sleeper, 42" Flatscreen TV/VCR/DVD/CD Player, and flows into an ample...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
7169 Harbourside II with Beautiful Marin...

This penthouse level villa has sweeping vistas of the entire Shelter Cove Harbour Marina. The villa itself consists of two floors. The first floor features an refreshed Queen bedroom and bathroom along with the kitchen, living and dining areas. ...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Large Three Bedroom Villa with Several U...

You're going to be amazed by this sizable three bedroom villa with numerous updates and a huge deck overlooking the George Fazio Golf Course!The main floor as you enter consists of one of two primary bedrooms, kitchen, dining and living room. The...

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

Hilton Head Tours & Activities

Cake Decorating

Color Me Greenville

Book online
$50.00 - $450.00

duration: 1 Hour 30 Minutes meeting_point: Color Me Greenville description: 1hr long party. Join us to decorate your own 5” cake! Booking includes unlimited buttercream, fondant, and sprinkles!

Cap
Cap

Historic Mitchelville Freedom Park

Book online
$25.00

pricing: $25 description: Cap

Private Excursion

Carolina Breeze Charters

Book online
$275.00 - $450.00

duration: 2 to 4 hour options meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Create your perfect day on the water with a custom, private charter aboard the Carolina Breeze, our...

Solaris - Fireworks Cruise

Vagabond Cruise

Book online
$695.95

duration: 2 Hours meeting_point: Hilton Head Island group_size: Private Charter for up to 10 passengers description: Book the Hilton Head summer time favorite Fireworks Cruise aboard the all new Solaris! **Our private charters accommodate up to 10...

Three Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$660.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Three Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$79.99

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...

Day with a Native - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

duration: 3 to 8 hours description: Choose from a range of half‑day to full‑day coastal excursions tailored to your interests—fish, hunt for shark teeth and fossils, crab like a local, paddle with dolphins in uncrowded areas, birdwatch, or...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

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...

Dolphin Cruise

Reel Native Fishing Charters

Book online
$65.00

description: See Dolphins Up Close! Duration 2 hours About We're committed to providing a stress-free experience to both new and returning clients. More info Minors must be accompanied by adults

2-Hour Day Sail

BC2 - Island Head

Book online
$19.99 - $49.99

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

Private Lesson with Clark Sinclair

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

meeting_point: George Fazio Course description: About Clark Sinclair, Director of Golf Clark Sinclair has been a member of the Palmetto Dunes staff since 1983 and has been teaching since 1986. He is a graduate of Presbyterian College. Clark...

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