Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront Villa, Heated Beachside Pool!

Welcome to Your Totally Remodeled Oceanfront Oasis! Everything new in 2025!!!This elegantly refreshed villa offers the ideal blend of modern luxury and coastal appeal. Recently completely refreshed, it features new floors, modernized bathrooms, and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Wonderfully Updated Three Bed Four Bath ...

This gorgeous completely refreshed three bedroom and four bathroom villa is ideal for families or golf/tennis/pickleball groups and the beach can be effortlessly accessed by a short walk or by calling the seasonal, on-call Palmetto Dunes Buggy. The...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Lovely condo walkable to beach access wi...

Beachwalk 129Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'129 Beachwalk is a charming single-story villa in Shipyard Plantation, a stone's throw from the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Hilton Head Vacation Rental steps away f...

This huge three bedroom and three bathroom villa overlooks the pool and is seconds from the beach! Upon entering the home there are two bedrooms on the first floor. The left bedroom features two Queen-sized beds and an en-suite bathroom with tub...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 11
Sunny & bright, dog-friendly condo w/ go...

Inverness 942Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Inverness Village, a complex located near golf courses, beaches, and so much more...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Dog-friendly villa with free WiFi, furni...

Evian 140Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Plan your next escapade to Hilton Head Island and book this marvelous and newly remodeled villa...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Guided Congaree National Park Kayak/ Canoe Tour

*Guided Congaree National Park Kayak/ Canoe Tour* _____________ Rates **Floating Options** * Single Kayak * Tandem Kayak * Canoes **Adult (Ages 13+):** $80 **Children (Ages 12 & under):** $50 ____________ Duration 3 Hours ____________ ...

Gift Card

Island Segway

Purchase the perfect gift: a gift card with a value of your choosing!

Hilton Head Yacht - Full Day Charter

Hilton Head Yacht Charter Company

Book online
$8,750.00

Top Shelf Yacht Charters are all about you. From adventure to anniversaries, relaxing to proposing, there's nothing we can't do for you during your cruise! Imagine your own floating resort! Experience 80 feet of pure opulence aboard Top Shelf. Our...

5 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$27.00 - $195.00

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 self pick up and drop off available. Attendant will text you lock...

Parasailing

H2O Sports

Book online
$95.00

duration: 8-10 minutes per parasail ride • Up to one 1 hour for entire trip 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...

Afternoon Half Day Sail Trip On Knot The Office Sailboat

About Set Sail for a half day adventure aboard our Monohull Sailboat. This trip is customizable for you and your group. Sail out to the Ocean and do some ocean sailing (providing conditions allow) or anchor and enjoy some water time off the boat...

Two Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$35.99

These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Private / 2 Hour Sunset Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$280.00

duration: 2 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: We recommend 8, if more please call. accessibility: Boats take 2 steps...

Private Tubing Trip

Island Head- Hilton Head Harbor

Book online
$250.00 - $550.00

Have a blast on a private tubing trip! About This is fun for everyone! Have a blast on a private tubing trip. Our captain will show your group a thrilling time as you tube the beautiful low country. This trip is private to your group and maxes...

One Hour Ocean Kayak or Stand Up Paddleboard Rental

Single Kayak 1 Hour Rental: $27.99 ________________________________ Double Kayaks or SUP 1 Hour Rental: $41.99

Sunset Cruise

Island Time Charters

Book online
$350.00 - $450.00

The most spectacular views and vivid colors! Duration 2 or 3 Hours About This Sunset Cruise allows access to the best locations in the Low Country to enjoy the breathtaking views. With the sunset on one side of the boat and a view of the...

Three Day Beach Cart Rental

Hilton Head Outfitters - Bike Rental

Book online
$25.99

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