Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Oceanfront getaway with lagoon views, sh...

Summary:Windsor Place 402The Space:Be sure to bring your bathing suit so you can swim in the oceanfront pool, relax in the hot tub, and tan on the huge deck at this resort complex. The pool area features a mushroom fountain and zero-entry pool for...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Fully Updated Kitchen and Bathrooms with...

As you enter this villa you are greeted by the open concept Kitchen, Dining and Living Areas. The Kitchen has been refreshed with tiled countertops, stainless steel appliances and bespoke cabinetry. The Dining Area has seating for six. The Living...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Updated all suite tennis villa with WD, ...

Summary:Tennismaster 102The Space:Boasting a screened outdoor living area, four flat-screen TVs, a gourmet kitchen, and all new furnishings, this stylishly refreshed 3BR/3.5BA villa in the Tennismaster community at Shipyard Plantation is your ideal...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Beachfront escape with pools, hot tub, a...

Summary:Island Club 5404The Space:Take a break at the beach at this oceanfront condo in the peaceful, 27-acre Island Club of Hilton Head! Outside, appreciate the fresh ocean air and plenty of sunshine from your furnished patio, while inside, you'll...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Beachfront escape with pools, hot tub, a...

Summary:Island Club 5404The Space:Take a break at the beach at this oceanfront condo in the peaceful, 27-acre Island Club of Hilton Head! Outside, appreciate the fresh ocean air and plenty of sunshine from your furnished patio, while inside, you'll...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Sunset Rentals | Evian 217

Your dream vacation starts at 217 Evian in Shipyard, Hilton Head Island, SC. This attractively refreshed 3 bedroom, 3 bathroom Shipyard villa will feel like your island-style home-away-from home. This 1,830 sq ft Hilton Head Island villa is...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Day Rental

Island Life Rentals and Tours

Book online
$15.00 - $70.00

duration: 1 Day description: *Perfect for your day exploring around Hilton Head!* ___________________________________ Additional Fees - **Basket** - $1.00 - **Helmet** - $5.00 - **Lock** - Free (1 lock per 2 bikes) About - Perfect for a day...

Four Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

4 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days cancellation_summary: 24 Hours in advance description: 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 4pm. After hours...

Baby Gear Rental • Six Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $175.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 6 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

Beach Gear Rental • Six Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Everything you need for a fun and comfortable day at the beach! Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than 5PM. Duration 6 Days About - Free delivery...

One Week Electric Bike Rental
Book online
$250.00

duration: 7 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...

Luxury Pontoon Rental with Fireworks Experience

description: 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...

Echaw Creek Tour

Nature Adventures Outfitters

Book online
$52.00 - $104.00

duration: 2 Hours cancellation_summary: Can Cancel up to 24 hours in advance for a full refund, Within 24 hours of the event there will be a $20 rebooking fee on any rescheduled tours. Tours cancelled by Nature Adventures Outfitters due to weather...

Four Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$645.00 - $935.00

description: Golf Cart Rentals! Duration 4 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Juneteenth Children’s Drum Camp

Historic Mitchelville Freedom Park

duration: 2 hours min_age: 3 max_age: 15 description: Let the rhythm lead the way at this hands-on children’s drum camp. Participants will learn basic drumming techniques, explore rhythm and movement in a group setting, and take part in a parade...

Kayak Tour

Port Royal Sound Foundation

Book online
$40.00 - $55.00

duration: 2 Hours description: Join a PRSF Naturalist for a 2-hour guided kayak tour of the Chechessee River departing from the Maritime Center. Children ages 5-12 must be on a tandem kayak with an adult (18+). Designed for all experience...

Party Cycleboat Tour

Bluewater Adventure Cycleboat

Book online
$49.95 - $1,250.00

description: Rates **Party of 2-20:** $1250 *Ages 21+* _____ Duration 2 Hours About Join us on the water on Hilton Head's first ever party cycle boat. We provide the coolers, ice, music and fun while our guests sit on cycle seats and enjoy...

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