Hilton Head, SC Vacations

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Featured Vacation Rentals

5 Bedroom Home w/ Private Pool & 6Seater...

Welcome to Island Impact Vacation Rental at 91 Sandcastle Court, Hilton Head, South Carolina! Constructed in 2020, this new single family home was designed with the goal to make many memories and allow others to do the same while on vacation. This...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 18
Cozy condo with balcony & pool- close to...

Sea Side Villas I 212Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to the newly remodeled beachfront condo in Hilton Head, SC, where luxury meets...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Fourth-floor condo with pools, hot tub, ...

Hilton Head Resort 4432Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stroll to the beach each morning and be greeted back in the afternoons by amazing...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Amenity-rich condo 50-yard walk to beach...

HH Beach & Tennis B127Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head, this beautiful snowbird-friendly (Dec-Feb) condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
2 Bedroom Second Floor Oceanfront Condo

They thought of everything when this charming two bedroom oceanfront villa was being refreshed! Combining an handsome modern beach design throughout while also focusing on comfort, the best of both worlds collide in this Hampton Place...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Fifth Floor Condo With Great Views of th...

Come appreciate this two bedroom and two bathroom condominium with fabulous ocean vistas! The Kitchen is on the right upon entering this penthouse-level condo and features granite countertops, new stainless steel appliances and bespoke cabinetry! ...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Pontoon Boat Rental

Island Head- Hilton Head Harbor

Book online
$275.00 - $2,200.00

*Explore the Low Country on your own!* ___________________________________ Rates and Duration **Two-Hour Rental:** $275 **Three-Hour Rental:** $375 **Four-Hour Rental:** $475 **Five-Hour Rental:** $549 **Six-Hour Rental:** $649 **Seven-Hour...

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...

Three Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$15.00 - $60.00

duration: 3 day bike rentals cancellation_summary: NO REFUNDS OR RAINCHECKS meeting_point: your address description: Bike rentals for a three day period. (Example: you rent the bikes on monday, they are due back thursday morning) what_is_included...

Sunset & Fireworks Tour

duration: 2.5 hours cancellation_summary: All reservations are subject to our 24 hour cancellation policy! group_size: Up to 12 people description: Experience the Magic of Summer Nights! Every Tuesday, Harbour Fest lights up the sky -- and there's...

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.

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

*Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* ___________________________________ Rates are per private charter **2 Hours** - $375*-Only Recommended for Small Children* **3 Hours** - $475 **4 Hours*...

Nine Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$70.99 - $141.99

9 Day Rental Rates: - 16” Kids Beach Bike: $70.99 - 20” Kids Beach Bike $70.99 - 24” Youth Beach Bike: $70.99 - 26” Bike w/ Child Seat: $85.99 - 26” Mens Beach Bike: $70.99 - 26” Unisex Beach Bike: $70.99 - 12" Balance Bike: $70.99 ...

Climb Club

Hilton Head Island Recreation Association

Book online
$100.00 - $550.00

duration: 4 Weeks • 1 Day Per Week meeting_point: Island Recreation Center min_age: 5 max_age: 15 group_size: Up to 10 people description: The Island Rec Center offers an exciting opportunity for young climbing enthusiasts with its Climb Club. ...

Day Trip to Savannah

Flip Flop Charters

Book online
$525.00 - $1,150.00

Cruise to Savannah! Duration - 5 hours - 6 hours About Avoid the traffic and cruise to Savannah in style. We’ll take you through the backwaters into the Savannah River and dock right on river street. You’ll be right at the heart of all...

Dolphin Nature Tours

Blue Pearl Marine Dolphin Tours

Book online
$45.00 - $165.00

This tour offers unparalleled views of the lowcountry. Wildlife in its natural environment and the beautiful prestine landscape that make up the famous Lowcountry. No trip is ever the same.. Each trip is an opportunity to experience something new...

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton Head Island as...

One Day Beach Cart Rental

Hilton Head Outfitters - Bike Rental

Book online
$14.99

WIDE ALL-TERRAIN BACK WHEELS provides easy roll over sand HOLDS ALL YOUR BEACH GEARS, carries cooler, beach towels, umbrellas and more! EASY OPEN AND CLOSING, opens in seconds and folds flat for travel and storage MULTI PURPOSE - can be used for...

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