Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Beautiful 3,104 square foot Palmetto Dun...
5.0
(1)

Heath 34Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located along the George Fazio Golf Course in a gated Palmetto Dunes Resort community, this completely...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
46 Folly Field, Quick Walk to Beach, Lar...

46 Folly Field is freshly remodeled home in the sought-after Folly Field area is a ideal blend of comfort and convenience for a Hilton Head vacation. With 4 bedrooms and 3 full bathrooms, it offers ample space for families or groups. The proximity...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Bright condo with beach access, pools, h...

Hilton Head Resort 3306Our 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 in Hilton Head, SC! This gorgeous 3rd-floor condo offers...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Modern condo with private patio - close ...
4.4
(27)

Queens Grant LatitudeOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor condo is the ideal place to set as a home base as you are out and about...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Penthouse Condo with Yacht Views!

This Penthouse vacation rental has expansive vistas of Shelter Cove Harbour and Marina where you can see all the way to Broad Creek! This villa has over 2500 square feet of living space making it one of only a handful of true Penthouse condos in...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
105 Barrington Arms- Totally Updated Oce...

Treat yourself and your family with this completely refreshed oceanfront condominium! This is a wall-in remodel. Everything is new!The kitchen is open and spectacular, with features such as Quartz countertops, stainless steel appliances, and bar...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Eleven Day Electric Bike Rental

duration: 11 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...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$475.00

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 Info It’s never...

Two Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $475.00

Electric Bike Rental Duration 14 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Beach Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

Everything you need for a fun and comfortable day at the beach! Duration 5 Days 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. ...

Bachelor/Bachelorette

Flip Flop Charters

Book online
$895.00

Explore Calhoun Street! Duration 4 hours About If you’re looking for a picturesque location to raise a glass and toast the happy couple, we’d love to help you celebrate! Waterfront bars are an excellent choice. With a stunning view of...

Boomerang 2 Private Charter Fishing
Book online
$540.00 - $630.00

Rate **Three Hour** - $540 **Four Hour** - $630 About The Boomerang 2 is a comfortable 28 foot Parker center console that is powered by two brand new Suzuki outboards. We specialize in fun, family fishing excursions where you don’t need...

Lessons

Daufuskie Marsh Tacky Society

Book online
$45.00 - $75.00

Duration 1 hour About We offer a handful of lesson options to meet the needs of a wide variety of individuals looking to grow their skills around horses on the ground and in the saddle. Appropriate for ages 7+ through adult, who are total...

Full Moon Glow Bike Tour

Glow Bikes Hilton Head

Book online
$41.00 - $50.00

Experience the enchantment of our Full Moon bike tour on glowing bicycles! Overview Unique moonlit tour on glowing bicycles 3 picturesque stops at Hilton Head Island landmarks Perfect for individuals, couples, families, and groups Create...

Morning Segway and Coffee
Book online
$115.00

Start your day on a caffeinated Segway ride! Duration 1.5 Hours About 50% Segway. 50% Coffee. 100% Fun! Join us for this fun & unique way to explore Hilton Head Island! This 2.5 hour tour will be one of the highlights of your vacation...

Trail Rides Experience - Montage Guests

duration: 1.5 hours meeting_point: Longfield Stables Trail Barn min_age: 8 group_size: Up to 5 people description: Embark on an unforgettable experience through the scenic Lowcountry of Palmetto Bluff. Our expertly guided rides take you through...

Three Day Double Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$55.99

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.

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...

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