Hilton Head, SC Vacations

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Featured Vacation Rentals

Welcoming villa with pool, beach access,...

Island House 138Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to the enchanting appeal of Hilton Head, SC, where white sandy beaches and acclaimed...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
2 Bedroom and 2 Bath Condo unit in Ocean...

The Island:Hilton Head Island may only be 12 miles by 5 miles wide, but you’ll find everything you need here for the ultimate Island getaway. Appreciate days basking in the sun on some of the best beaches in the country. Get into the swing of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanside Resort Condo w/ Indoor Pool, T...

Hilton Head Resort 4434Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in a gated community and located near the sandy shores of the Atlantic Ocean...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Boutique Updated Home with Much to Offer...

Treat your family to this gorgeously refreshed home with four bedroom and three and half bathrooms! The kitchen will come entirely-equipped and features multiple updates like granite countertops and stainless steel appliances. A enormous island...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Free Tennis & Pickleball, 3 minutes to b...

NEW to Rental Market, NEW renovationsPROPERTY IS AVAILABLE FOR SHORTER STAYS. 3 NIGHT STAYS IN THE FALL and WINTER. Any arrival and departure date!!HILTON HEAD ISLAND. This is an oceanside villa complex that's just a short walk to the beach. The...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Something for everyone- private pool on ...

This amazing home has something to offer everybody with its four bedrooms and four bathrooms, private pool and spa. The kitchen is enormous and features ample storage and prep space, stainless steel appliances, island cooktop and bar seating for...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 9

Hilton Head Tours & Activities

Stand Up Paddle Boarding Tour

Hilton Head Island Recreation Association

Book online
$40.00

duration: 1.5 hours meeting_point: Rowing and Sailing Center description: Your 1.5hr stand up paddle board trip will explore the marshes of Skull Creek. An educational Lowcountry experience learning and working with the tides, oysters, and...

SCM PVT Dolphin Eco 6p

*Our Most Popular Boat Trip!* --- Description Explore the marsh and search for the infamous Atlantic Bottlenose Dolphin... Join us for a tour on Broad Creek watching for birds and dolphins in the salt marsh ecosystem. Explore Broad Creek...

Beach Gear Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Everything you need for a fun and comfortable day at the beach! Duration 6 Days About - Free delivery and pickup - Beach gear is delivered the **morning after check-in** and will be picked up the night before check-out no later than 5PM. ...

Same Day E-Bike Rental • 9AM-4PM(up to 7 hours)
Book online
$30.00 - $55.00

Same Day: Electric Bike Rental Duration up to 7 Hours must be returned by 4:00pm same day 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...

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

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 explore and...

One Month Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$180.99 - $361.99

One Month Bike Rental Rates: - 16” Kids Beach Bike: $175.99 - 20” Kids Beach Bike $175.99 - 24” Youth Beach Bike: 175.99 - 26” Bike w/ Child Seat: $190.99 - 26” Mens Beach Bike: $175.99 - 26” Unisex Beach Bike: $175.99 - 12" Balance...

Blue Granite Express

The South Carolina Railroad Museum

Book online
$15.00 - $120.00

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...

Bonjour Private Charter

BC2 - Island Head

Book online
$550.00 - $5,500.00

duration: 1-10 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 35 People description: Bonjour – Hilton Head’s Premier Charter Boat Step aboard Bonjour, Hilton Head’s newest and most luxurious charter boat, built...

Ten Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $400.00

Electric Bike Rental Duration 10 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...

Solaris - Morning Sightseeing Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate up to 6 passengers, ensuring an intimate and...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Morning Cruise

Seaglass Charters LLC

Book online
$650.00 - $750.00

*Beat the heat and enjoy a Beautiful Morning Cruise, We can explore the waterways and Islands around Charleston in the cool of the day!* Duration 2 & 3 Hour Sails About A great time of day to see the harbor. Bring your suit and we will go...

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