Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Brigantine Quarters, Shipyard Plantation...

If you have never experienced the Brigantine Quarters then we encourage you to do so. It is a delightful gated community. Our condo is located in a secluded part of Shipyard Plantation called Brigantine Quarters. We offer a 2 bedroom, 2 full bath...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lovely villa near the water with hot tub...

Queens Grant 759Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape from the hustle and bustle of everyday life to this peaceful villa located within a...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Great Ocean views, Oceanfront Heated Poo...

Welcome to Carolina Beach Club 429.This elegantly refreshed 4th-floor oceanside villa features new floor, furnishings, appliances, and kitchen countertops throughout.The villa includes two bedrooms and two bathrooms, with a combined living and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Inviting Hilton Head Island vacation Ret...

Discover a relaxing escape at our inviting Hilton Head Island vacation rental, ideally located with gorgeous vistas of the George Fazio Golf Course. This striking getaway offers a harmonious blend of comfort, ideal for your next hideaway.Located on...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beautiful Home with Private Pool located...

Sit back and relax in this striking three bedroom plus loft home with sweeping vistas of the award winning George Fazio golf course. Several updates were finished in 2024 further enhancing the appeal this home provides! Upon arrival you'll notice...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
2nd floor renovated end unit w/ stunning...

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.435 Captain's Walk overlooks the pool out to the ocean! Lots of recent updates!435 Captain’s Walk is a second-floor, 3-bedroom, 3-bathroom end unit that...

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

Hilton Head Tours & Activities

Private Fishing Charters

Performance Fishing Charters

Book online
$550.00 - $1,400.00

Hilton Head’s premiere fishing charter! Duration 3-8 Hour Rentals **Up to 4 people** Possibility for 5 with children About Located on Hilton Head Island, your charter will be guided by Captain John Cloyd, a USCG licensed captain...

Beach Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

Everything you need for a fun and comfortable day at the beach! Duration 24 Hours About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than 5PM. ...

Luxury Pontoon Rental with Fireworks Experience

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 later than 8...

Crescent City Cocktails: A Taste of New Orleans

Step into the spirited traditions of New Orleans with this hands-on cocktail class celebrating the classics that made the Crescent City a cornerstone of cocktail culture. From refined sippers to bold, celebratory pours, this experience channels...

Life Under the Sea

Coastal Discovery Museum Hilton Head

Book online
$5.00

There is a magical world full of fascinating creatures under the sea! Join knowledgeable Museum staff and volunteers in the Discovery Lab to explore, touch, create, play, and learn more about ocean life. Who lives in those shells? What does a crab's...

Two Day Schools

Palmetto Dunes Golf Academy

Book online
$750.00

Duration & Rates - 2 Days, 3 hours of instruction per day - $750 per student About The small group 4:1 student:teacher ratio promotes important quality attention. Skill levels can be mixed and the instructor is able to meet the unique needs of...

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...

Luxury Sparkling Wine & Champagne Tasting

duration: 1 Hour min_age: 21 description: Experience the art of celebration with our Luxury Sparkling Wine & Champagne Tasting, where every sip tells a story of elegance, tradition, and terroir. Set against the charming backdrop of Honey ...

SeaFood Fest Adventure Camp

Hilton Head Island Recreation Association

Book online
$100.00

duration: 2 days • 3 hours per Day meeting_point: Rowing and Sailing Center min_age: 7 max_age: 14 group_size: Up to 20 Campers description: Under the guidance of two Master Naturalists, children will explore the delicate balance of our...

Ten Day Electric Bike Rental
Book online
$400.00

duration: 10 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Native Plant Sale

Coastal Discovery Museum Hilton Head

Come and join us for the next Coastal Discovery Museum annual Native Plant Sale in October 4th from 10 am - 1 pm. The sale will take place at the Coastal Discovery Museum on the Honey Horn grounds. Over 90 species of native plants will be...

Brunch Under Sail

BC2 - Island Head

Book online
$19.99 - $89.00

duration: 2 Hours meeting_point: Broad Creek Marina 18 Simmons Rd. description: A Luxury Brunch Sailing Experience Step aboard our luxury catamaran for a truly elevated morning on the water. Brunch Under Sail is a two-hour sailing experience...

Find your perfect Hilton Head

Fishing Charter

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