Hilton Head, SC Vacations

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Featured Vacation Rentals

Island oasis with balcony, beach access,...

Island Club 4106Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'An memorable trip to Hilton Head awaits at this bright and ideally located condo sitting mere...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
10 Iron Clad- Luxury Ocean Front Home, 6...

Welcome to 10 Iron Clad, a handsome multi-level, ocean front home in the award-winning Palmetto Dunes Resort. With breath taking ocean vistas from nearly every room, your family is sure to savor their beach vacation. A one million dollar remodel...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 17
Stunning Oceanfront Villa! Heated Beach ...

Discover the ultimate beachfront escape at 409 Ocean Dunes, where every detail has been thoughtfully redesigned to enhance your Hilton Head experience. Recently modernized, this villa offers an exceptional oceanfront view on one of the island's best...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Amazing & newly updated three bedroom / ...

**METAL ROOF REPLACEMENT SCHEDULED BETWEEN SEPTEMBER 2025-APRIL 2026 AND IS SUBJECT TO CHANGE. SCAFFOLDING WILL BE UP AT TIMES THROUGHOUT THE PROJECT. Due to the nature and scope of the work there is a possibility that your accommodations may be...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Mid-Island Retreat | 2 Pools, Hot Tub, 1...

Fiddlers Cove 19KOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the gated Fiddler's Cove community, this 2BR/2BA condo offers a relaxing top-floor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2nd-Floor Condo w/Balcony, Fast WiFi, Sh...

Fiddlers Cove 17HOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Surround yourself with nothing but tranquility and peaceful at this family-friendly...

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

Hilton Head Tours & Activities

Three Hour Vanishing Island and Dolphin Nature Watch Tour
Book online
$375.00 - $395.00

*Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

Guided Paddleboard Tour

Island Head- Hilton Head Harbor

Book online
$40.00

*Be one with the water* ___________________________________ Rates **Person:** $40 *Ages 12+* ___________________________________ Duration 1 hour ___________________________________ About Stand Up Paddleboarding focuses on creating core...

13 Day Rental

Island Life Rentals and Tours

Book online
$51.00 - $355.00

___________________________________ 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...

Private Sunset Cruise

Unwritten Charters LLC

Book online
$600.00 - $900.00

Enjoy a Beautiful Sunset Cruise! Duration 2 or 3 Hours About Unwritten Charters will provide bottled water and soda. You and your guests are welcome and encouraged to bring on board your own food and adult beverages (for those 21 and up) for...

2-Hour Sunset Sail

BC2 - Island Head

Book online
$19.99 - $99.00

duration: 2 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Guided Kayak Tour

H2O Sports

Book online
$45.00 - $90.00

duration: 2 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...

Hilton Head Full Moon Cruise

Island Head - Broad Creek

Book online
$59.99

Get on the water under a low country full moon! Duration 90 minutes About This is a one of a kind experience to see a full moon from the water. Enjoy a 90 minute slow cruise as you take in the beauty of the low country in a spectacular...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$75.99 - $151.99

10 Day Rates: - 16” Kids Beach Bike: $75.99 - 20” Kids Beach Bike $75.99 - 24” Youth Beach Bike: $75.99 - 26” Bike w/ Child Seat: $90.99 - 26” Mens Beach Bike: $75.99 - 26” Unisex Beach Bike: $75.99 - 12" Balance Bike: $75.99 - Adult...

Romantic Sunset Cruise

Island Time Charters

Book online
$399.00

The most spectacular views and vivid colors! Duration 2 Hours About Come aboard for an enchanted, romantic cruise! Bring your favorite bottle of bubbly and we will provide the rest. This charter includes a sweet treat, fresh flowers, and...

2 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$18.00 - $100.00

*Perfect for your day exploring around Hilton Head!* ___________________________________ 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...

Day Camp Sessions

Daufuskie Marsh Tacky Society

Book online
$425.00

Campers learn practical, natural horsemanship and riding skills! Duration 10 minutes About Youth (ages 7-17) are welcome to participate in one or more week long day camp sessions. Campers learn practical, natural horsemanship and riding...

Nightly Rental.  Premium 4 Passenger Electric Golf Cart. Pick up and drop off at rental address only

About 48 Volt Electric Golf Cart with 2023 Trojan Lead Acid Batteries.. Equipped with seat belts, anti lock brakes, extended top, LED headlights (high and low beam), turn signals, horn, and digital gauges. More info - Riding weight...

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