Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront, 3rd floor villa with corner ...

Summary:Sea Cloisters 311The Space:Immerse yourself in the soft blues of the ocean both inside and out at this oceanfront condo in the Sea Cloisters. Wake up each morning to a expansive view of the Atlantic, sit down for breakfast on your breezy...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful Palmetto Dunes Villa- Lagoon V...

Summary:Queens Grant 762The Space:Welcome to your serene hideaway in Hilton Head, SC! This gorgeous three-bedroom, three-bathroom villa is located within the photogenic Palmetto Dunes' 11-mile lagoon system, offering a ideal blend of relaxation and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Hilton Head Condo w/ Covered Balcony + P...

Leave your worries behind and stay at this freshly refreshed 2-bedroom, 2-bathroom vacation rental condo in Hilton Head! Comfortably sleeping up to 6 guests, this unit is within walking distance to the beach, eateries, shopping, and more. You'll...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Second-floor condo with balcony, shared ...

Summary:Village House 206The Space:Village House 206 is a elegantly refreshed condo offering a prime location near the beach! Located in the Village House in Port Royal Village, this condo is well-maintained and decorated with a light and airy...

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

Summary:Cutter Court 923The Space:You will definitely appreciate your next vacation to Sea Pines when staying in the heart of world-famed Harbour Town in this handsome villa at 923 Cutter Court, this pristine roomy gem is a gorgeous third-floor...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beautiful Three Bedroom Villa with Sweep...

You'll be glad you picked this sizable and smartly decorated three bedroom and three bathroom villa located in Turnberry Village. Throughout this elegant villa you'll adore the modern beach-centric decor. The kitchen has been refreshed with...

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

Hilton Head Tours & Activities

SC Pimento Cheese Sponsor

Red Maple Event

Book online
$500.00 - $3,000.00

duration: 5 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: Promote your business in front of the crowds at the SC Pimento Cheese Festival This free, family friendly event will draw crowds from all over the state. There...

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

meeting_point: Hilton Head Island, SC description: Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to...

One Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$34.99

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...

Private Family Or Group Fishing Trip Aboard The Drifter

duration: 3 Hours cancellation_summary: 72 Hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way group_size: 32 people pricing: The Private Family or Group Fishing Trip Aboard the Drifter has a set price of $995 for a group size of 16 people or...

Three Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$480.00

description: Duration 3 Hours ___________________________________ About Catch sharks, other species, might catch some nice fish and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

Wonderful Wings

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $25.00

description: *Get up close and personal with local butterflies!* ___________________________________ Rates - **$6 per adult, $6 per child (Geared to preschool age & younger children, but fun for the whole family!) - **3 and under, no...

Bare Boat Rental without a Captain - Full day 9am to 6 pm, No Overnight Stay

meeting_point: Hilton Head Island, SC description: *Bareboat Sailboat Rental With out a Captain* Full day sail, bring your own Captain Duration 9 AM - 6 PM

Twelve Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $450.00

description: Electric Bike Rental Duration 12 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

Beach Comber & Vanishing Island

Dolphin Discoveries Hilton Head

Book online
$69.75 - $395.00

duration: 3 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: Duration 3 Hours About Learn the secrets of Hilton Head’s history and the fascinating stories that bring it to life. This 3-hour expert guided tour takes you to five nearby historic sites in an air-conditioned bus. You will...

Private Inshore Charter Fishing aboard Hobo
Book online
$440.00 - $540.00

duration: 3 Hours cancellation_summary: 48 hours meeting_point: Drifter Excursions, 86 Helmsman Way, Palmetto Bay Marina group_size: Licensed for up to 16 passengers; rate includes 6 passengers pricing: - **Two-Hour Charter** - *$440* - Includes 6...

PB Palmetto Bluff Biking The Bluff

duration: 2 Hours meeting_point: Palmetto Bluff, Bluffton pricing: Starting at $70 per Guest description: *Palmetto Bluff is a bicyclists paradise!* Take a bike tour through Palmetto Bluff’s 20,000 acres, which include historic architecture...

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