Hilton Head, SC Vacations

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Featured Vacation Rentals

Second-floor condo in beachfront complex...

Summary:Spa On Port Royal Sound 2217The Space:Find every essential for a fun-filled beach vacation at this refreshed, second-floor condo at The Spa on Port Royal Sound. As part of this oceanfront complex, you'll appreciate painless access to the...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Dog Friendly with pool, tennis, covered ...

Summary:Evian 129The Space:Welcome to your serene hideaway in Hilton Head, SC! This impressive top-floor Evian end unit condo offers beautiful golf vistas and is located within the ocean-aligned Shipyard community. With three roomy bedrooms and two...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 9
Lovely Palmetto Dunes Villa Getaway with...

Summary:Moorings 37The Space:This splendid two bedroom condo is located in the fashionable Palmetto Dunes Plantation and provides a shining outdoor pool. Take a complimentary shuttle to Shelter Cove for dining and shopping, or walk to attractions in...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
This fully renovated Hilton Head Vacatio...

This gorgeously remodeled Hilton Head vacation rental offers a opulent coastal escape. It is located on the 4th floor with elevator access for simple arrival. The cavernous living room features a sizable mounted flat-screen TV and direct access to a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Redesigned Ground-Floor Villa with Pools...

Fiddlers Cove 11COur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your ideal island hideaway awaits at this freshly redesigned 2BR/2BA ground-floor villa at...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Bedroom Centre Court Villa with Lagoon...

This villa is centrally located within the Palmetto Dunes Tennis & Pickleball Center. It’s ideal for golfers, pickleballers, and tennis players. Let’s not forget the families who want to spend time at the beach. A short, level 10-min. walk will...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Charleston, SC to Jersey City

The Bluewater Academy

Book online
$5,250.00

duration: 7 days meeting_point: 3190 Suite C Matecumbe Key Rd, Punta Gorda, FL 33955 description: The Northern Corridor: A Masterclass in Endurance and Extended Passage making Charleston, South Carolina to Jersey City, New Jersey | June 7th...

Sunset Cruise

Flip Flop Charters

Book online
$595.00

description: Breathtaking sunsets! Duration 2 hours About Join us for a 2 hour cruise through the intracoastal to take in Hilton Head’s breathtaking sunsets. There’s no better place to take in the beauty of the sun setting over the...

Independence Day Float-a-Palooza

Saluda Lake Landing

Book online
$5.00 - $20.00

duration: 12pm-6pm max_age: 101 group_size: 300 description: Independence Day Float-a-Palooza Celebrate Independence Day weekend on the water at Saluda Lake Landing! Join us July 3rd, 4th, and 5th from 12 PM–6 PM for three days of floating...

19' Stingray Rental

H2O Sports

Book online
$325.00 - $750.00

duration: 2-6 hour rentals 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: Boat holds 6...

Blue Granite Express

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Guests enjoy a narrated 90-minute trip through Fairfield County countryside. Seating on the train is on board an open-air car, allowing easy viewing as...

2026 Juneteenth Celebration

Historic Mitchelville Freedom Park

Book online
$10.00

duration: 6 Hours description: Join us for an unforgettable day at the 12th Annual Juneteenth Celebration at Historic Mitchelville Freedom Park — a community gathering filled with music, culture, food, and family-friendly fun. Spend the day...

Five Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$215.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a...

Gullah Celebration Cruise

Vagabond Cruise

Book online
$90.00

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 80 passengers description: Join us for an extraordinary experience aboard the exquisite Spirit Of Harbour Town, as we embark on a captivating journey this year. Indulge in the...

Two Day Single Stroller

Hilton Head Outfitters - Bike Rental

Book online
$35.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** These strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Maritime Center Eco Tour

Beaufort Dolphin Adventures

Book online
$20.00 - $40.00

duration: 90 Minutes cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund in case of operator cancellation due to weather. meeting_point: Port Royal Sound...

Guided Congaree National Park Kayak Tour

meeting_point: The Congaree National Park description: *Guided Congaree National Park Kayak Tour* _____________ Rates **Floating Options** * Single Kayak * Tandem Kayak **Adult (Ages 13+):** $80 **Children (Ages 12 & under):*...

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...

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