Hilton Head, SC Vacations

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Featured Vacation Rentals

Exquisitely updated with Incredible view...

Unwind on your private deck and take in impressive vistas of the Robert Trent Jones Golf Course Savor cooking at home in this refreshed, completely equipped kitchen that includes bespoke cabinets, new countertops, and stainless steel appliances. The...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Inviting villa with on-site golf, tennis...

Golfmaster 1301Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your favorite vacation memories will be effortlessly curated when you call Lowcountry Legacy, a...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Centrally located condo with shared pool...

Hilton Head Cabanas 75Our 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 coastal getaway in Hilton Head, SC! This cavernous 2-bedroom villa...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 9
Updated Harbour Town Hideaway with Pool ...

Racquet Club Villas 2346Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the Racquet Club Villas, adjacent to Harbour Town on Hilton Head Island...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Shorewood, Unit 530 | Penthouse condo in...

Shorewood 530Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'THE ELEVATOR FOR SHOREWOOD 530 WILL BE OUT OF SERVICE FOR UPGRADES FROM JAN 12th - FEB 28th 2026...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Walk to the beach Top-floor penthouse wi...

Village House 403Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You'll be within walking distance of the Westin Resort at this three-bedroom, four-bathroom...

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

Hilton Head Tours & Activities

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

*Perfect for your day exploring around Hilton Head!* ___________________________________ 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...

Paint the Pony - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

Beachcombing & Eco Tour (2 Hrs)

Beaufort Dolphin Adventures

Book online
$353.77

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

Holiday Market

Coastal Discovery Museum Hilton Head

Holiday Market - November 25,2025 10AM- 1PM We will have local authors and artists on site as well as food tastings. Buy a special gift for your special someone for the holidays.

6 Hour Fishing Charter

Awesome Adventure Charters

Book online
$865.00

Allows You More Range and Time for a Well-Rounded Fishing Adventure! Duration 6 Hours About Whether going for that trophy fish, pursuing world-class tarpon in the ocean, or enjoying the scenery while fishing the salt marsh, you’re sure to...

Two Week Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$59.99

The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

Dolphin Tour

Daufuskie Difference

Book online
$15.00 - $30.00

Experience the thrill of encountering dolphin in their natural habitat while taking in breathtaking views of Tybee’s serene coastal waters. From historic lighthouses, to majestic Fort Pulaski, to dolphins playing next to the boat, our tours offer...

Multi Day Destination sail with Overnight Stay

Anchors Away Sailing Charters

Book online
$1,275.00 - $1,425.00

*Multi-Day sail to a destination of your choosing* Stay onboard the boat overnight at the dock Duration Up to you!

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Hibachi Dinner Cruise Experience an...

Friday Feeding Frenzy!

Coastal Discovery Museum Hilton Head

Book online
$15.00 - $20.00

Duration 1 Hour About TGIF ... even for our animals! Our reptiles, amphibians, fishes, and marine invertebrates all know that Friday means FRIDAY FEEDING FRENZY! Join our animal care staff and learn the ins and outs on how we care for and feed...

Segways & Smoothies Tour

Island Segway

Book online
$109.00

A Smoothie hits the spot! Duration 1.5 Hours About 50% Ride, 50% Smoothie, 100% Fun Segways are for every day of the week and Smoothies and Boba Tea is refreshing on a HOT day. This Segway tour takes you all around the south end to find an...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time Each Way cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Hilton Head -> Daufuskie Island...

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