Hilton Head, SC Vacations

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Featured Vacation Rentals

4 bedroom/4.5 bathroom home with private...

This striking Hilton Head home features a roomy rooms, a huge private pool area, and great golf course vistas. The great room opens to the dining area and kitchen. A deck off the living area offers a table for outdoor dining and stairs leading to...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Fourth-floor condo with pools, hot tub, ...

Hilton Head Resort 4432Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stroll to the beach each morning and be greeted back in the afternoons by fantastic...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3 Shore Crest, Chefs Kitchen, Free Golf,...

3 Shore Crest Lane, Hilton Head Island. Luxury awaits in this bespoke-constructed 5-bedroom home in Burkes Beach, just a 5-min. walk to the beach and adjacent to Chaplin Park. Appreciate high-end finishes, a chef's kitchen, sunroom, covered deck...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Pristine Condo with shared pools, hot tu...

Crown Reef 104Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC, located within the serene Port Royal...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Renovated home with private screened poo...

Carolina CottageOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend balmy days outside swimming in the screened backyard pool, barbecuing at the lagoon's...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Spacious waterview haven with decks, fir...

Sound Villas 1452Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A cavernous haven in the Sound Villas community, this family-friendly home is a sure bet for...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 15

Hilton Head Tours & Activities

All-Inclusive Sunset Supper Cruise

Daufuskie Difference

Book online
$44.50 - $89.00

Join us on the most popular Sunset Dinner Cruises Hilton Head has to offer! Departing from Broad Creek Marina every Friday at 4pm. The 50-minute Ferry ride is accompanied by fascinating Lowcountry history and stories. Along the Broad Creek and into...

Sunset Celebration Dolphin Cruise

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: Enjoy all of the beauty the low...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

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 minimum...

Family Fishing Session

Catmandoo Sport Fishing

Duration 2-6 Hours Rates **Private Session:** 2 Hour Trip - $395* 3 Hour Trip - $495* 4 Hour Trip - $650* 5 Hour Trip - $850* 6 Hour Trip - $995* *Prices are for up to 4 passengers. We can take up to 6 people on our shorter trips(2hr&3hr...

Twilight Guided Ghost Story Tour

Mungeon Creek Golf Cart Rental

Book online
$61.32 - $235.85

duration: 2 Hours group_size: Up to 20 guests description: Ride into the haunted history of Daufuskie Island with our Twilight Guided Ghost Story Tour! Join us for a chilling 2-hour adventure as the sun sets and shadows creep across the island. Your...

Flyboard 20 Minute

Carolina Hydrofly

Book online
$99.00

20 Minute Flyboard Pro Series Experience What's Included? 15 Min Flight Time. Includes 10 minutes of instruction time, fuel, life jacket, wetsuit, and helmet We advise everyone to arrive at least 30 minutes before your start time. If...

Private Sunset Cruise

Unwritten Charters LLC

Book online
$600.00 - $900.00

Enjoy a Beautiful Sunset Cruise! Duration 2 or 3 Hours About Unwritten Charters will provide bottled water and soda. You and your guests are welcome and encouraged to bring on board your own food and adult beverages (for those 21 and up) for...

Gift Cards

Dolphin Seafari

Shared / BeachComber & Vanishing Island

Dolphin Discoveries Hilton Head

Book online
$69.75

duration: 3 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. group_size: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

Vista Bar Crawl Tour

SC Pedal Parlor

Book online
$30.00 - $400.00

Rates • Adult - $30-35 if booked individually • 21+ years of age • Fits up to 16 people total • Private and public options available • Private tours discounted if you have more than 12 individuals • "Public" tours must have 10 riders...

Private / 1.75 Hour Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00

duration: 1.75 hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from dock...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$475.00

Fish like a local! Duration 3 Hours About Targeting Red Drum, Black Drum, Seatrout, Flounder, and Sheepshead in local tidal creeks and nearby waterways with light tackle. This trip is great for all experience levels! More Info It’s never...

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