Hilton Head, SC Vacations

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Featured Vacation Rentals

Relaxing Condo with pool near Beach, Sho...

Xanadu C6Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head's Forest Beach area, this beautiful condo offers the ideal blend...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
First Floor Condo near the beach with be...

Shorewood 107Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel the ultimate beach hideaway at this impressive oceanfront condo in Hilton Head, SC. Just...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Gated community home w/ vaulted ceilings...

Queens Grant 717Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for a modest family hideaway or charming escape for two, Queens Grant 717 is a appealing...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Shipyard Condo next to pool, near tennis...

Tennismaster 302Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Marriott Vacation Club Villa

This property is located in Hilton Head. The public area overlooks the water but there is no beach access. However there is a shuttle that takes guests to the beach for no charge. You just call for a pick up! There is on-site parking, elevators to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Waterfront condo w/ private balcony, W/D...

Port II Villas 1613Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Port II Villas 1613, a impressive condo located on the gorgeous Hilton Head...

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

Hilton Head Tours & Activities

Three Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$60.00 - $300.00

description: Rent with us! Duration 21 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...

Two Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

description: Enjoy miles and miles of scenic bike paths Duration 2 Days 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...

Lowcountry Seafood Experience

May River Excursions

Book online
$135.00

meeting_point: Hudson's Seafood Restaurant description: Rate - $135 per person includes boat excursion as well as a meal and one beverage __________ Duration - 2 Hour Boat Excursion with meal afterwards at Hudson's ____________ About ...

Nature Hike

Port Royal Sound Foundation

Book online
$10.00

description: Join us for a 1.5 mile exploration hike! Duration 1.5 Hours About Meet at the Maritime Center and enjoy a nice morning hike! This Naturalist-led hike is roughly 1.5 miles through maritime forest and salt marsh. Ages 3 & up ...

Full Day Fishing Trip

BackCountry Light Tackle & Fly

Book online
$895.00

description: Duration 8 Hours About Light Tackle and/or Fly Fishing Experience Explore more localized waters from the Departure Boat Ramp! 375 lbs maximum (all passengers): - 2 Adults - 1 Child, 1 Adult - 1 Adult

Sweetgrass Basket Workshop

Coastal Discovery Museum Hilton Head

Book online
$80.00

description: *Learn traditional basket making from an expert!* ___________________________________ Duration 2 Hours ___________________________________ About Learn about the history of the Sweetgrass basket, one of the Lowcountry’s...

Shelter Cove Marina Kayak & Stand Up Paddleboard Rental

description: *Want to explore the Lowcountry waters on your own? We have paddleboards and kayaks you can rent!* --- Description Outside Hilton Head has a fleet of safe and comfortable boards & kayaks that you can rent to enjoy the area's...

4 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days cancellation_summary: 24 Hours in advance description: 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...

Canoe Rental

Wateree Marina

Book online
$25.00 - $50.00

description: Canoe Rentals What to Bring - Valid Driver's License - Major Credit Card

Tuesday night Firework Sailings

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

description: About Night time Fire Work sailing charter! More info **Pricing:** • 1-6 people: $600.00 and $100 for each additional person up to 14. ($1,400) • 15-20 people is a flat $1,500.00

St. Patrick's Day Cruise

Island Head - Broad Creek

Book online
$99.00

duration: 10 Hours (2 Hour Boat Ride Each Way) cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Enjoy St. Patricks Day in...

Two Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$345.00 - $525.00

description: Golf Cart Rentals! Duration 2 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

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