Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Sunset Rentals | Gloucester 79
4.5
(4)

Make cherished memories that will last forever when you treat your family to an island vacation in this 4 bedroom, 3 bathroom vacation home located in the charming Shipyard Plantation on Hilton Head Island. Gloucester 79 is a gorgeous Shipyard home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Vibrant condo with tennis courts, pool, ...

Spa On Port Royal Sound 3322Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'You won't want to miss this calming slice of serenity for your next vacation trip...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Oceanfront Palmetto Dunes condo with ama...

Barrington Court 409Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the beauty of Hilton Head Island from this completely updated one-bedroom condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Luxurious 4 Bedroom with many Updates!

This charming Hilton Head Island vacation rental offers a ideal blend of luxury and comfort for your next hideaway. The cavernous living room provides plenty of room to relax and relax, with comfortable seating and a welcoming ambiance for gathering...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Coastal condo with indoor and outdoor po...

Spa On Port Royal Sound 1314Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal beach hideaway in Hilton Head, SC! This appealing condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Dog Friendly ~ Walk to the beach ~ Scree...

Attractively decorated 3 bedroom, 3 bath villa with master and 2nd bedroom on the main floor (each with their own bathroom!). New floors on the first floor freshly installed! 3rd bedroom has its own separate bathroom upstairs. Sleeps 6 adults...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Baby Gear Rental • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $100.00

duration: 3 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Private / 3 Hour Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$270.00

duration: 3 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...

New Exhibition: Opening Reception

Coastal Discovery Museum Hilton Head

duration: 5:00PM - 7:00PM description: The Coastal Discovery Museum, a Smithsonian Affiliate, opens a retrospective exhibition, “It's Thursday! Artists of the Round Table,” on November 12, celebrating 15 prominent local artists who gathered...

Fireworks & Guaranteed Dolphin Tour

Dolphin Discoveries Hilton Head

Book online
$69.75 - $445.00

duration: 3 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: Max of 6 (Check Out Our Rentals w/ Captain for Larger...

Vanishing Mile Isle Tour

Cross Island Cruises

Book online
$399.00

duration: 2 hours 30 minutes meeting_point: 68 Helmsman Way group_size: Maximum 6 people pricing: $399, for up to 6 passengers per boat. description: On the Vanishing Mile Isle Beachcombers Tour, guests can expect a unique and adventurous experience...

Private Lesson with George Spinella

Palmetto Dunes Golf Academy

Book online
$90.00 - $450.00

About George Spinella George Spinella graduated from Siena College in 2003 and the San Diego Golf Academy in 2005. He is the 1st Assistant at the George Fazio Course and has been teaching with Palmetto Dunes since 2006. George enjoys teaching...

Three Week Rental (Walk Up)

South Beach Bike Rentals

Book online
$165.00 - $393.00

Enjoy miles and miles of scenic bike paths Duration 3 Weeks About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also available ...

Creek Cat Tour

Lowcountry Watersports

Book online
$120.00 - $145.00

duration: 2 Hours 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 min_age: 5 group_size: 2 people per creek...

Workshops

Coastal Discovery Museum Hilton Head

Book online
$5.00 - $35.00

duration: varies cancellation_summary: • Cancellation Policy: Full refund minus $5 admin fee prior to one day in advance. No refund if cancelled within one day. description: Join us for a dynamic series of hands-on, creative workshops designed...

Private Party

Palmetto Axes

Get the joint all to Yourself! About *Ages 12+ • Up to 36 People* All the fun for you and as many people as the fire marshal will let in the place. Book 2 plus hours and save even more! - Bring in your own food - Maximum of 36 people per...

Three Day Schools

Palmetto Dunes Golf Academy

Book online
$1,690.00

Duration & Rates - Three days, four hours of instruction per day. - $1,690 per student About The Three-Day School is very popular because of the extra time built into the program to process what students learn during the instructional periods...

PB Private SUP Instruction
Book online
$75.00 - $325.00

*Get on the water with one of our custom kayak tours & classes* Outside Palmetto Bluff has a professional staff of Instructors ready to help you enjoy the fun, fitness and beauty of the fastest growing watersport in the world! All lessons...

Find your perfect Hilton Head

Fishing Charter

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