Hilton Head, SC Vacations

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Featured Vacation Rentals

Gorgeous and sunny home with pool, beach...

Kingston Dunes 68Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sophisticated, modern, cavernous, and private, the ideal Hilton Head Island hideaway exists...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's palmetto and oak trees. Walking paths and boardwalks give you fast and simple access to the community's beach area.After...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
Spacious Hilton Head Island Vacation Ren...

This roomy Water Oak villa offers the ideal setting for families and golf groups looking to appreciate everything Hilton Head has to offer. With a thoughtful layout, multiple en-suite bedrooms, and painless access to the community pool, it provides...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
1st floor condo with pool, tennis, patio...

Spa On Port Royal Sound 3136Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this striking first-floor condo in Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Great Hilton Head Location Pet Friendly,...

This property is now under new ownership and the owners are keen to make this already handsome and roomy home lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a striking 6-bedroom, 5.5-bathroom, pet...

  • Hilton Head
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 18
Near Robert Trent Jones golf course with...

This Water Oak villa rental has accommodations for ten and is located near the Robert Trent Jones golf course with just short walk to the beach. The Primary -suite is on the first floor with its king bed, HDTV and private en-suite bathroom. The...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Jet Ski Rental

Timberlake Marina

Book online
$250.00 - $700.00

duration: 4.5 or 8.5 Hours min_age: 23 group_size: Maximum capacity is 2 people description: There’s nothing quite like a day on Lake Murray—wide open water, sunshine reflecting off the surface, and miles of shoreline waiting to be explored. At...

Baby Gear Rental Package • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$190.00 - $235.00

duration: 3 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Donuts with Dolphins Aboard Dolphin Seafari

duration: 1.5 hours cancellation_summary: Full refund with 24 hours notice; call 843-785-2345 for cancellations or guest changes. group_size: Holds up to 20 people accessibility: Handicapped accessible pricing: * Adult - $45 * Child (12 and under) ...

Marriott Vacation Club Daufuskie Tour

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

Four Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: 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...

11 Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$86.46 - $205.81

description: Enjoy miles and miles of scenic bike paths Duration 11 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...

Cake Decorating

Color Me Greenville

Book online
$50.00 - $450.00

duration: 1 Hour 30 Minutes meeting_point: Color Me Greenville description: 1hr long party. Join us to decorate your own 5” cake! Booking includes unlimited buttercream, fondant, and sprinkles!

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...

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...

Marsh Critters

Coastal Discovery Museum Hilton Head

Book online
$10.00

description: *Learn about the creatures of the salt marsh ! Great for families with younger children.* ___________________________________ Rates - **$10 per person aged 3 and up, under 3 Free** ___________________________________ ...

Vanishing Island Expedition™ - Three Hour

Island Life Rentals and Tours

Book online
$65.00 - $780.00

duration: 3 Hours group_size: 12 - 14 Max description: Our Three-Hour Beach Combing Expedition to "Vanishing Island™" starts at The Old Oyster Factory docks near the top of Broad Creek. As we glide through the Lowcountry Salt Marsh, you'll watch...

Happy Hour Cruise

duration: 90 minutes cancellation_summary: 48 Hours meeting_point: 1 Shelter Cove Lane pricing: $75 per adult (adults only) description: Set sail for the perfect start to your evening with Outside Hilton Head’s adults-only Happy Hour Cruise aboard...

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