Hilton Head, SC Vacations

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Featured Vacation Rentals

9 Singleton Beach, Ensuites in Every Bed...

**NOW OFFERING 50% OFF POOL HEAT FOR MARCH - MAY 22*** UPON BOOKING, GUEST MUST LEAVE IN COMMENTS THAT THEY WANT POOL/ SPA HEAT OR CALL OUR RESERVATIONS TEAM TO CONFIRM. THIS IS FOR NEW BOOKINGS MADE ON OR AFTER 1/30/26*****WINTER/ SPRING 2026...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
SAVE! LOW SPRING RATES.ABSOLUTELY BEAUTI...

PERFECT SPRiNG GETAWAY FOR FAMILIES AND COUPLES SEEKING A BEAUTIFUL AND COMFORTABLE, STREET ENTRY VILLA IN PALMETTO DUNES RESORT. An definitely charming family vacation villa in Top Rated Palmetto Dunes Resort in HHI. A ideal family hideaway and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Quiet Waterfront Condo with WiFi - Pools...

Island Club 2502Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Soak up the striking vistas of the Atlantic Ocean from the balcony of this comfortable Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Ideal house for families in Sea Pines wi...

Looking for the ideal getaway? Look no further. This pretty, fifth row home in Sea Pines has everything you’re looking for! And it Is just a five min. walk to the beach and a 10 min. walk to The Salty Dog.Ideal for families, golfers, retirees, and...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Short walk or bike ride to the beach and...

This comfortable two-bedroom, three-bath Water Oak villa comfortably sleeps up to six guests, making it ideal for families visiting Hilton Head.The first-floor primary suite features a king bed, flat-screen TV, and a private bathroom with a walk-in...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 5
Large and Update Single-level Queens Gra...

Welcome to this attractively modernized, two-bedroom Queens Grant villa on the Robert Trent Jones Golf Course! From the moment you step inside, you’ll be captivated by the bright, beach-inspired décor that sets the ideal tone for a calming...

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

Hilton Head Tours & Activities

Pirate Cruise

Pirates HHI

Book online
$10.00 - $39.99

duration: 1.5 Hours cancellation_summary: Full Refunds are issued with 48 hours advanced notice meeting_point: 86 Helmsman Way, Hilton Head, SC 29928 - Check In at the Lowcountry Watersports Office to the left of Black Marlin Restaurant pricing...

One Month Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$80.00 - $400.00

description: Rent with us! Duration 30 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and...

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...

PB Private Stand Up Nature Walk
Book online
$95.00 - $325.00

description: *Stand-up paddleboarding is easy to learn, a fantastic workout, and lots of fun!* _____________ _____________ About Take a naturalist guided stand up paddle tour of the coastal salt marsh. An unbelievable perspective! ...

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of history.

Hilton Head Seafood Festival Daufuskie Island History Experience

description: Step Back in Time on Daufuskie Island Tucked between Hilton Head and the mainland, and accessible only by boat, Daufuskie Island is often described as “the other side of the river” — a hidden gem where time seems to stand still...

Private Disappearing Island Dolphin Tour
Book online
$379.00

duration: 2 Hours • All Ages cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 group_size: Maximum 6...

SCM Private SUP Yoga
Book online
$45.00 - $325.00

duration: 1.5 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head Island min_age: 12 group_size: 10 pricing: $225 for up to first 3 people $60 each additional person description: Find your flow where the river meets the sky...

28 Day Rental

Island Life Rentals and Tours

Book online
$96.00 - $740.00

duration: 28 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

1 Hour Dolphin Tour

H2O Sports

Book online
$25.00 - $350.00

duration: 1 hour tour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Up to 14...

Two Day Electric Bike Rental
Book online
$120.00

duration: 2 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...

PB Private Freshwater Kayak Fishing

meeting_point: Palmetto Bluff, Bluffton description: *We have pioneered kayak fishing on the east coast!* ___________ About This is one of the fastest growing sports and is offered in the Inland Waterway Trails at Palmetto Bluff. The Hobie Pro...

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