Hilton Head, SC Vacations

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Featured Vacation Rentals

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
8 Bedroom/8.5 Bathroom Large Luxurious H...

This roomy 4th row Palmetto Dunes home is the ideal place for a enormous family hideaway or golf trip! The beach path is directly across from the home and the multiple indoor and outdoor living spaces, this home makes for an ideal getaway for any...

  • Hilton Head
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 26
3rd row Ocean Luxury - Private Pool/Spa ...

Welcome to our luxury 7BR, 6.5BA coastal escape in North Forest Beach—just 75 steps or 3 mins. down a private path to the sand. Designed for multi-generational gatherings, this home features high-end furnishings, hotel-quality linens, a chef’s...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Oceanfront condo w/free WiFi, balcony, s...

Sea Cloisters 305Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sea Cloisters 305 is a striking, two-bedroom, two-bathroom, oceanfront condo in the complex...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Cozy Third-Floor Condo w/ Fast WiFi & Ba...

Fiddlers Cove 11JOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located just a short walk from Folly Field Beach and conveniently close to grocery stores...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Family-friendly condo with lagoon views,...

Colonnade Club 181Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway at the Colonnade Club in Hilton Head, SC! Located within the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7

Hilton Head Tours & Activities

Lake Wylie Private Charters

Captain Jake's Guide Service

Book online
$250.00 - $600.00

duration: 3-8 hours meeting_point: Lake Wylie Boat Ramp-890 Nivens Landing Dr Fort Mill, SC 29708 description: Whether you're looking for an action-packed day of tubing and island hopping or a laid-back cruise to soak in the views, we’ve got you...

Deck the Porch

Brice Herndon Draft Horse and Carriage Company

Book online
$100.00

Ride in our Vis-a-vis Carriage A more intimate and private setting with your own personal horse and driver. Enjoy private time with your family or make it a couple's adventure strolling through the Front Porch of the Lowcountry! Seating Up to...

Solaris - Morning Sightseeing Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate seven to ten passengers, ensuring an...

One Week Double Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$69.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miled of bikes paths.

Afternoon Harbor Cruise

Seaglass Charters LLC

Book online
$750.00 - $850.00

Come enjoy a couple of hours on the water with us! Duration 2 Hours About This two hour cruise in the harbor will take you to The Battery, The Ravenel Bridge, and out to Ft. Sumpter. A great way to see Charleston from a completely different...

2 Hour Private Afternoon Sail and Dolphin watch on Knot The Office

*Afternoon Sail* Generally a breezy afternoon leading to some of our most exciting sailing all day. Come and experience true sailing without running the motor. Take the helm and help with handling sails if you desire, but either way, kick back...

Three Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$175.00 - $199.00

Single Kayak Full Day Rental: $175 ________________________________ Double Kayaks Full Day Rental: $250

Revolutionary War Lecture Series

Coastal Discovery Museum Hilton Head

Book online
$7.00

duration: 1 hour cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. min_age: 13 group_size: 60 description: Join us for "Revolutionary Reflections", a...

Shelter Cove Marina Kayak & Stand Up Paddleboard Rental

*Want to explore the Lowcountry waters on your own? We have paddleboards and kayaks you can rent!* --- Description Outside Hilton Head has a fleet of safe and comfortable boards & kayaks that you can rent to enjoy the area's waters on your...

Pony Rides

Daufuskie Marsh Tacky Society

Book online
$10.00

Duration 10 minutes About Do you have a child that's either totally horse crazy or slightly horse curious who would delight in a chance to sit in the saddle? Allow us to provide a memorable, confidence building experience while introducing them...

9 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$39.00 - $275.00

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. Attendant will text you lock...

Indigo Tie Dye Party

Coastal Discovery Museum Hilton Head

Book online
$15.00

Come and join in the tie dyeing fun! Twist, twirl, tie, and dye with natural indigo dye. Why indigo dye? In 1739 Eliza Lucas Pinckney’s experiments with the indigo plant resulted in a very profitable cash crop for South Carolina. Enjoy a fun...

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