Hilton Head, SC Vacations

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Featured Vacation Rentals

2 bedroom/2 bathroom 4th Floor Oceanfron...

**WINDOW AND DOOR REPLACEMENT PROJECT TENTATIVELY SCHEDULED September - April 2026 AND IS SUBJECT TO CHANGE. SCAFFOLDING WILL BE UP DURING THIS TIME. Due to the nature and scope of the work there is a possibility that your accommodations may be...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Villa with WiFi, Private Washer & Dryer,...

Fiddlers Cove 10EOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Have the vacation of a lifetime at this second-floor condo. Prepare a picnic in the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
133 Dune Ln, Oceanfront, Pool, Free Golf...

133 Dune Lane, Hilton Head Island is a 4-bedroom, 4-bath oceanfront home epitomizes casual beach living at its best. Wake up to charming vistas of the ocean from every room, including the kitchen, living room, dining room, and all four bedrooms. The...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 14
Well Updated with Beach Contemporary Dec...

This refreshed, gorgeous two bedroom, two bath villa is located directly beside the Robert Trent Jones Driving Range and Clubhouse and is also just steps to the pool! You will feel instantly on vacation as you enter this coastal villa! The warm and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Spacious updated oceanfront condo with s...

Windsor Place 207Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Cavernous 2nd floor, corner villa is ideal for families, couples, and friends traveling...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Ground-floor condo near beach with pool ...

Island House 129Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'White sandy beaches, acclaimed golf options, and Lowcountry appeal await you at this Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Private Surf Lessons

Forest Beach Surf & Cycle

Book online
$100.00

Come enjoy a day of Hilton Head Surf Lessons! Duration 1 hour About Our friendly and expert Surf Instructors will have you up on your board and riding waves on day one. Please schedule lessons one week in advance HEAD SURF INSTRUCTOR, JT...

Baby Gear Rental • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $100.00

Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 1 Day About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Beach Gear Rental • Two Days

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 48 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. ...

Island Head Inshore Fishing

Island Head - Broad Creek

Book online
$495.00 - $1,125.00

duration: 3 - 8Hours description: Join us for an unforgettable inshore fishing adventure aboard our 21-foot Parker center console. Whether you're a beginner or an experienced angler, our trips are tailored for fun, excitement, and reeling in the...

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 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...

Two Day Beach Cornhole

Hilton Head Outfitters - Bike Rental

Book online
$55.00

PORTABLE CORNHOLE SET – This tailgating game includes 2 portable cornhole boards (2x3 feet), 8 all-weather regulation bean bags, and cornhole Rules. For travel, tailgating, beach, lawn, or backyard WATER FILLED - Lightweight travel cornhole boards...

SCMEA Marsh Kayaking

Fripp Island Golf and Beach Resort

The Ultimate Fripp Island Adventure! Duration 2 Hours About Share a tandem kayak with a buddy or paddle yourself in a single. Kayaking through the marsh is the ultimate Fripp adventure with the chance to see dolphins, terrapins, birds, and...

Trail Rides Experience - Palmetto Bluff Members

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...

4th of July Fireworks Cruise

Drifter Excursions

Book online
$25.00 - $50.00

*Fourth of July – Join us for the spectacular Harbour Town display.* ___________________________________ Rates - **Adults** - $50 - **Kids** - $25 - **Babies** - Free! ___________________________________ About - To view the fireworks...

Shark Fishing Excursion

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** - $350.00 **3 Hours** - $450.00 **4 Hours** - $550.00 **5 Hours** - $650.00 Each additional passenger over 6...

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...

4.5 Hour Deep Sea Fishing Aboard the Drifter
Book online
$65.00 - $1,000.00

*Fishing for the whole family on Hilton Head Island!* ___________________________________ Rates - **4.5 Hour Deep Sea Fishing:** - $75 ___________________________________ About - The Drifter is a 60-foot long party fishing boat that has...

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