Hilton Head, SC Vacations

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Featured Vacation Rentals

HHBT C10 | Upgraded, Great View, Resort ...

Welcome to Hilton Head Beach and Tennis C10, a relaxing getaway located on a beachfront resort in the heart of Hilton Head, South Carolina. Set in the breathtaking Folly Field Beach area, this chic vacation condo promises the ideal coastal...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Golf getaway condo near the beach with p...

Queens Grant 684Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Whether you're spending your days by one of the on-site pools, teeing it up at one of the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Inviting villa with pool, tennis, & balc...

Forest Beach Villas 120Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Forest Beach Villa is the closest you can get to Coligny Beach Park and shopping and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Stunning Oceanfront View! Heated Pool
4.6
(12)

Ocean Dunes 320: A Premier Oceanfront Getaway!!Discover the appeal of Ocean Dunes 320, a elegantly designed oceanfront villa that combines modern comfort with striking Atlantic vistas. This inviting getaway offers all the amenities of home...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Lovely townhome with balcony, tennis & W...

Ketch Court 821Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your next Hilton Head vacation playing tennis, practicing your drive, and calming on the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Second-Floor Condo with WiFi, Pool, Golf...

Plantation Club 431Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This villa has a view of the Sea Pines' Heron Point Golf Course, a jetted tub, and access...

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

Hilton Head Tours & Activities

Ultimate Adventure

Hilton Head Helicopter Tours

Book online
$189.00

description: The Ultimate Adventure is an aerial flight that travels the full stretch of Hilton Head Island and the eastern shores of Daufuskie Island, offering expansive coastal views and memorable family moments. Passengers will fly over iconic...

Two Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $475.00

description: Electric Bike Rental Duration 14 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...

Private Guided Tours

Historic Mitchelville Freedom Park

Book online
$10.00

duration: 1 hour description: Step into one of the most powerful stories in American history with a private guided tour of Historic Mitchelville Freedom Park—tailored exclusively to your group. This is more than a tour. It’s a personal journey...

Beach Discovery Tour

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Join a museum naturalist on an amazing nature tour!* ___________________________________ Duration 1.5 Hours ___________________________________ About Ever wonder who makes those holes in the sand—or when and why sea turtles...

DI 6 Hour Ultimate Lowcountry Day

meeting_point: Daufuskie Island, SC description: *Customized adventures are the best way to see and do the Lowcountry!* --- Description Designed for the family or small group interested in experiencing an authentic day in coastal South...

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...

CCHH Kayak Tour

Outside

Book online
$35.00

meeting_point: Hilton Head Island, SC description: *Explore Hilton Head's waterways by kayak with an interpretive naturalist guide* --- Description Discover the Hilton Head tidal marsh by kayak… Bring the family kayaking through the tidal...

13 Day Rental

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Private Food Tour

Food Tours Hilton Head

Book online
$695.00

description: Customize Your Tour! Duration 3 hours What's Included: - A private luxury SVU pickup for 6 - A knowledgeable tour guide About This tour is made especially for you. After you book the tour, our tour guide will contact you...

Tuesday night Firework Sailings

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

description: About Night time Fire Work sailing charter! More info **Pricing:** • 1-6 people: $600.00 and $100 for each additional person up to 14. ($1,400) • 15-20 people is a flat $1,500.00

Shrimping

May River Excursions

Book online
$300.00 - $400.00

description: *Experience sea life like never before!* ___________________________________ **Please note**: Shrimping is only available from August-December ___________________________________ Rates **Private Charter** - $300 2 hours (for 6...

Kayak Club

Hilton Head Outfitters - Bike Rental

Book online
$300.00 - $450.00

description: Valid through 2026 calendar year Unlimited kayak rentals for membership holder and 50% off rentals for additional guests on booking. Applies to One Hour Kayak or Canoe Rental, 1.5 Hour Kayak or Canoe Rental, and Two Hour Kayak or...

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