Hilton Head, SC Vacations

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Featured Vacation Rentals

Large Updated Three-Bedroom Condominium ...

This enormous three-bedroom Hampton Place condominium sits oceanfront and has been wonderfully refreshed.Indulge in the ultimate beach vacation at this handsome 3-bedroom oceanfront getaway. Located on the charming first floor, this condo offers...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Oceanfront beach villa in Palmetto Dunes

Oceanfront Luxury in Windsor Court – Hilton Head IslandFeel the ultimate beachfront hideaway in this impressive 2-bedroom, 2-bathroom oceanfront villa in the highly sought-after Windsor Court community on Hilton Head Island. Wake up to beautiful...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Hilton Head Spinnaker-Shipyard Plantatio...

Spinnaker at Shipyard, 2 story townhouse, deck overlooks lagoon and golf course, includes 2 bicycles, complimentary golf and tennis each day for 2, impressive outdoor pool with grilles and play areas.Gated community with miles of bicycle trails, ...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Tuscan-Style Waterfront Retreat!

Welcome to your Mediterranean dream home! A beautiful Tuscan-style getaway ideally located along the relaxing 11-mile lagoon. This charming residence features four roomy bedrooms, a additional bunk room, and a completely air-conditioned private...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Centrally located condo with pool, tenni...

Cordillo by the SeaOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Snowbird special 15% off for stays over 28 days now through February Located in the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Panoramic view of the George Fazio Golf ...

Delightfully decorated and open floor concept villa is conveniently located just a few steps to the community pool pavilion, Shelter Cove Harbour Marina, as well as the countless resort amenities. You will fall in appreciate with this coastal beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2

Hilton Head Tours & Activities

Four Day Bike Rental

Wheelz of Hilton Head

Book online
$43.00 - $86.00

description: Four Day Bike Rental Rates Duration 4 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...

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...

Home School Learn To Row

Hilton Head Island Recreation Association

Book online
$40.00 - $100.00

duration: 4 Weeks • 1 Day Per Week meeting_point: Rowing and Sailing Center min_age: 12 max_age: 18 group_size: Up to 12 Campers description: Learn the basics of rowing. We use 1-4 person shells (boats) and will teach participants basic sculling...

Outdoor After School - Monday

Hilton Head Island Recreation Association

Book online
$150.00 - $600.00

duration: 4 Weeks • 1 Day Per Week meeting_point: Island Recreation Center min_age: 8 max_age: 14 group_size: Up to 20 Campers description: This is an after-school program hosted by Outdoor Rec where kids ages 8-14 can receive assistance...

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

Private Sunset & Fireworks Cruise - 12p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$500.00 - $600.00

description: Fish like a local! Duration 3 Hours About Targeting Red Drum, Black Drum, Seatrout, Flounder, and Sheepshead in local tidal creeks and nearby waterways with light tackle. This trip is great for all experience levels! More...

Sunset Beach Photography

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations may be rescheduled or fully refunded if no suitable time is found meeting_point: 64 Bradley Beach Road, Hilton Head Island, SC 29928 description: Want to commemorate a special...

Glow Splatter Painting AND Cake Decorating
Book online
$45.00 - $425.00

duration: 2.5 hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: Prices start at $600 description: You asked, we listened!! Now you can book a party for Cake Decorating and Splatter Painting!...

Hilton Head Island History Bus Tour

Coastal Discovery Museum Hilton Head

Book online
$49.00

description: 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...

Ohana Low Country Paddle Festival VIP Cruise

description: Saturday, September 6th 8:30-11 am Meets at: Rowing and Sailing Center at Squire Pope Community Park 137 Squire Pope Rd, Hilton Head Island SC 29926 The cruise will include: -Custom Pickney Island circumnavigation on the luxury...

Oktoberfest at The Landing

duration: 12pm-8pm max_age: 101 group_size: 300 description: Celebrate Oktoberfest lakeside every weekend at Saluda Lake Landing! Join us every Saturday and Sunday from September 20 through October 19, from 12 PM to 8 PM, for a fun and festive...

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