Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Newly Renovated! Hilton Head Resort #141...

Come check out one of Vacation Ready Services new Hilton Head Resort condos! Located on the 4th floor of Building #1, this newly managed and designed unit is the ideal hideaway for the whole family! This 2 bed & 2 bath island hideaway is equipped...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sea Pines Home on 18th Hole of Atlantic ...
4.8
(9)

Carolina OaksOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gorgeously positioned among the palmettos and oaks on the 18th hole of the Atlantic Dunes Golf...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Comfortable condo w/ shared pool, short ...
4.8
(8)

Queens Grant 565Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in Palmetto Dunes Plantation 565, Queens Grant is a two-bedroom, two-bath...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
A Quiet Beach Getaway with Pools, Hot Tu...
4.9
(12)

Island Club 3106Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'With walk-out beach access, two patios, and nine tennis courts, this Island Club villa is just...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Dreamy Island Gem W/ Golf Course View, P...
4.6
(7)

Heritage Villas 2229Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An memorable island vacation is never a bad idea especially when it comes to being perched...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lovely One Bedroom Condo with Atlantic O...
5.0
(1)

Treat yourself with this generously appointed one bedroom two bathroom condominium in esteemed Windsor Court! The kitchen will provide everything you need to prepare for your family. Looking beyond the kitchen pass-through you'll find bar seating...

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

Hilton Head Tours & Activities

St. Patrick's Day Cruise

Island Head - Broad Creek

Book online
$99.00

duration: 10 Hours (2 Hour Boat Ride 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: Enjoy St. Patricks Day in...

Open Climb

Hilton Head Island Recreation Association

Book online
$5.00 - $20.00

duration: 1-3 Hours cancellation_summary: Cancellation Policy: To be eligible for a full refund, all cancellations must be made up to 24 hours before the scheduled start time. We can also move you to another session time if spots are...

Bourbon & Beyond: Stir, Shake, and Sip
Book online
$95.00

Step into the world of bourbon and craft timeless, whiskey-forward cocktails in Bourbon & Beyond, an immersive mixology class at Hilton Head Distillery. Whether you're a seasoned bourbon enthusiast or just beginning to explore America’s native...

Half Day Flats Fishing (4 Hrs)

Green Heron Adventures

Book online
$500.00

Duration 4 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target red fish (red drum) in shallow mud/sand flats and creeks...

Palmetto Bluff

Flip Flop Charters

Book online
$625.00 - $750.00

Beautiful Scenery Duration - 3 hours - 4 hours About Nestled on the scenic May River is Palmetto Bluff, an idyllic community on 20,000 acres. Within the community is an extensive nature preserve, private residences, a hotel, several...

Beach Wheelchair

Hilton Head Outfitters - Bike Rental

Book online
$65.00 - $199.00

All Terrain Beach Wheelchair is designed to allow easier access to the beach. It is especially helpful for the individuals with lower extremity or mobility disabilities or spinal cord injury.

Hack, Snack and Roadie Ride

Daufuskie Marsh Tacky Society

Book online
$450.00

Duration 3.5 Hours Please Note This is experience is designed for novice or better riders who are comfortable with longer hours in the saddle and are able to independently mount/dismount their horses easily, this culinary and riding adventure...

Afternoon Harbor Cruise

Seaglass Charters LLC

Book online
$750.00 - $850.00

Come enjoy a couple of hours on the water with us! Duration 2 Hours About This two hour cruise in the harbor will take you to The Battery, The Ravenel Bridge, and out to Ft. Sumpter. A great way to see Charleston from a completely different...

Deliberately Unpredictable: Art Beyond Tradition

Coastal Discovery Museum Hilton Head

duration: various description: Main Gallery Exhibit what_is_included: Art from Cindy Chiappetta, Arla Wible, Vickie Jourdan, Sharon Licata, Mark Larkin, Margaret Crawford, Jo Dye, Earline Allen, Donna Varner, Joanna Chalson, John Crum and Linda Tully

Private Food Tour

Food Tours Hilton Head

Book online
$695.00

Customize Your Tour! Duration 3 hours What's Included: - A private luxury SVU pickup for 6 - A knowledgeable tour guide About This tour is made especially for you. After you book the tour, our tour guide will contact you and find out...

One Week 2 Chairs and 1 Umbrella Package

Hilton Head Outfitters - Bike Rental

Book online
$69.99

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.

1.5 Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$48.99 - $69.99

Single Kayak 1.5 Hour Rental: $43.99 ________________________________ Double Kayaks or Canoes 1.5 Hour Rental: $56.99 __________ Triple Canoe 1.5 Hour Rental: $69.99

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