Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Tree-lined home with beautiful patio, de...

WildwoodOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find your new favorite beach hideaway at this gorgeous coastal home, located the lush woodland...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Amazing golf views from almost every roo...

This comfortable end unit Hilton Head Island villa has tons of light with great vistas of the tee and greens at the Robert Trent Jones golf course. It also has the benefit of being close to the beach so you can comfortably walk or bicycle for a day...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Family-friendly villa w/ golf course vie...

Water Oak 15Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Water Oak 15 offers fairway vistas of the adjacent Robert Trent Jones Golf Course and is just a...

  • Hilton Head
  • 4 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Relaxing Condo with pool near Beach, Sho...

Xanadu C6Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head's Forest Beach area, this beautiful condo offers the ideal blend...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Comfortable condo with a pool, hot tub, ...

Fiddlers Cove 16DOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Golfers and beach bums alike will adore this comfortable condo, just mins. from multiple golf...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming condo near Coligny Beach Plaza ...

Seascape Villas 3230Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate island hideaway at Seascape Villas 3230 in the heart of Hilton Head, SC...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Sunset Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

Stunning Sunset Views About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Stunning sunset views over the water and...

PRSF Lecture Series: White Shark Conservation

Port Royal Sound Foundation

Book online
$10.00

duration: 1 hour meeting_point: 310 Okatie Highway accessibility: Wheelchair accessible description: Dive into the fascinating world of white sharks as we explore cutting-edge research projects happening right here in the Northwest Atlantic. This...

Old Town Bluffton

Flip Flop Charters

Book online
$725.00 - $850.00

Explore Calhoun Street! Duration - 3 hours - 4 hours About Avoid the bridge and cruise up the May River to Old Town Bluffton. We’ll dock at the Calhoun street dock at the beautiful Wright Family Park. From there you can take a short walk up...

Dolphin Watching Cruise

Flip Flop Charters

Book online
$595.00

See dolphins in their natural habitat! Duration 2 hours About The Lowcountry is home to several pods of Atlantic Bottlenose Dolphins. Join us for a 2 hour cruise to see them in their natural habitat and take in the beauty surrounding Hilton...

One Week Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$39.99 - $129.99

One Week Rental Rates: - 16” Kids Beach Bike: $64.99 - 20” Kids Beach Bike $64.99 - 24” Youth Beach Bike: $64.99 - 26” Bike w/ Child Seat: $79.99 - 26” Mens Beach Bike: $64.99 - 26” Unisex Beach Bike: $64.99 - 12" Balance Bike...

One Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

Electric Bike Rental Duration 7 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 without...

Marriott Vacation Club Daufuskie Tour

Tucked between Hilton Head and Savannah, and only accessible by boat, Daufuskie is a must-see in the Lowcountry!

2 Day Rental

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 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...

Four Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

Enjoy miles and miles of scenic bike paths Duration 4 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

Ten Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$78.60 - $187.10

Enjoy miles and miles of scenic bike paths Duration 10 Days About Free locks with all rentals. Baskets and helmets also available - please select during check-out! More info Free locks with all rentals - please select during...

Eight Day Bike Rental

Wheelz of Hilton Head

Book online
$55.00 - $110.00

Eight Day Bike Rental Rates Duration 8 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect getting around...

3 Hour Adventure Cruise

Hilton Head Boat Charters

Book online
$445.00 - $925.00

duration: 3 Hours cancellation_summary: We need at least 72 hours' notice for a full refund. meeting_point: 43 Jenkins Island Rd, Hilton Head Island, SC 29926 group_size: Up to 20 People description: This is your "Best of the Low Country" day on the...

Find your perfect Hilton Head

Fishing Charter

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