Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Expansive Views of the Pool, Lagoon and ...

Located on the 3rd floor, this attractively refreshed two-bedroom, two-bath villa offers striking vistas of the community pool and the Atlantic Ocean. Ideal for a calming hideaway, it’s appealingly located within the Barrington community. It...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Riveting condo home with hot tub, sauna,...

Summary:Hilton Head Resort 4226The Space:NOTICE: Make this adorable condo your resting spot for your next vacation! Check out Folly Field Beach Park (just a little less than two miles out from your home away from home) and rest simple on sandy...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Newly renovated 2-bedroom, 2.5 bath Vill...

Make yourself at home in this phenomenal 2-bedroom Hilton Head getaway. This villa features a comfortable living room with 2 couch beds, ideal for calming after a day of exploring. The bedrooms feature a queen bed and two twin-XL beds, ensuring a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Water view condo with covered deck, on s...

Summary:The Cottages 30The Space:A modern island escape awaits at this condo at the Cottages. Located in the resort community of Shipyard Plantation, this condo offers convenient on-site access to a range of amenities including a world-class tennis...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
4 BR Private Home Close to South Beach M...

6 Beachside Drive | One Minute Walk to the Beach*4 Bedrooms | 3 Bathrooms*Sleeps 8*1 King, 1 Queen, 4 Twins*3 TVs | DVD | Alexa | Wi-Fi | Keurig*8 Beach Towels for Guest Use*Beach Gear Credits Included *Savor Rounds of Golf & Kids's Activities with...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Condo near beach with 2 pools, restauran...

Summary:HH Beach & Tennis B8The Space:Find a true escape in the luxe comfort of this pretty resort condo that has been newly remodeled (2024) to provide you with the ultimate vacation experience! This snowbird-friendly home away from home is part of...

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

Hilton Head Tours & Activities

Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$49.75 - $269.00

duration: 1 hour 45 minutes cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, above kayaks. max_age: 1000 group_size: 6 passengers accessibility: Boats take 2 steps...

Luxury Pontoon Rental with Fireworks Experience

description: Fireworks Pontoon Party Boat Rental and private VIP box for Harbourfest Fireworks Show! Captain your own adventure as you head out on a 2-hour self-guided cruise on a luxurious Bentley pontoon boat. Return to Shelter Cove Marina no...

Luxury Pontoon Rental
Book online
$315.00 - $815.00

meeting_point: Shelter Cove Marina description: This pontoon offers spacious dual captain's chairs, comfortable sofa-style seating and enhanced style. Can accommodate up to 12 passengers. Includes: -Cooler -Bluetooth Radio

Nine Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $295.00

description: Electric Bike Rental Duration 9 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...

Old Town Bluffton Farmers Market Cruise

Duration 4 Hours About Immerse yourself in the blissful charm of Old Town Bluffton, with this unforgettable excursion down the beautiful May River and get dropped off on the all new Calhoun Street Dock and Park in the heart of it all...

DI PVT Shark Tooth 12p

duration: 2 Hours meeting_point: Daufuskie Island group_size: Up to 12 guests pricing: $975 description: Enjoy a scenic boat ride from Daufuskie Island to Savannah, where you will step off onto islands to search for the fascinating artifacts that...

Intro to Stand Up Paddleboarding

duration: 1.5 Hours meeting_point: Hilton Head Island, SC pricing: description: *Stand-Up Paddleboarding is easy to learn, a fantastic workout, and lots of fun!* Launch your Stand-Up Paddle Boarding career with this intro to SUP lesson in...

Self-Guided Tours

Historic Mitchelville Freedom Park

duration: 6 Hours description: Discover the rich history of Mitchelville at your own pace with our Self-Guided Tours at Historic Mitchelville Freedom Park This flexible tour option allows you to explore the birthplace of freedom for formerly...

Gift Card

Drifter Excursions

description: Purchase the perfect gift: a gift card with a value of your choosing!

13 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$51.00 - $355.00

duration: 13 Days description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours self pick up and drop off available...

Hilton Head Yacht Cruise

Salt Shaker Charter LLC

Book online
$3,750.00 - $6,600.00

duration: 4 - 8 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Your Cruise, Completely Customized! At Salt Shaker Charter, every cruise is tailored to you. From intimate getaways to...

Curator's Tour

Coastal Discovery Museum Hilton Head

duration: Hour description: The Coastal Discovery Museum, a Smithsonian Affiliate, opens a retrospective exhibition, “It's Thursday! Artists of the Round Table,” on November 12, celebrating 15 prominent local artists who gathered weekly at The...

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