Hilton Head, SC Vacations

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Featured Vacation Rentals

The Spa at Port Royal Sound 3237

Hilton Head Island has been ranked the #1 Island in the Continental U.S. and #1 Island in the U.S. by readers of Travel + Leisure Magazine and Conde Nast Traveler for the past numerous years. In my slightly biased opinion you just can't find a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Relaxing Condo with pool near Beach, Sho...

Summary:Xanadu C6The Space:Located in the heart of Hilton Head's Forest Beach area, this appealing condo offers the ideal blend of convenience and tranquility. Just a short walk or bicycle ride away from Coligny Plaza, where you can discover a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Oceanfront Villa with Shared Pool, Hot T...

Summary:Island Club 5501The Space:This fifth-floor, oceanfront Island Club villa is a prime hideaway for your next oceanside vacation. Each guest has access to the complex’s many recreational facilities, including the shared pool/hot tub complex...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Sunny getaway with full kitchen, furnish...

Summary:Hickory Cove 18The Space:Start your mornings with peaceful golf course vistas and the convenience of being just a short walk from the beach at this comfortable getaway. Inside, you’ll find a well-equipped full kitchen, a dining area with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Ocean Oriented Oasis!  Indoor Heated Poo...

Welcome to Ocean Walk 106!Ideal for families and groups traveling together, Ocean Walk 106 combines two neighboring first-floor condos into one roomy and comfortable vacation getaway. With two bedrooms, two full bathrooms, and accommodations for up...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Sunset Rentals | Villamare 3223

Villamare 3223 is a 2nd floor, 2 bedroom, 2 bath villa in the extravagant Villamare complex at Palmetto Dunes Resort on Hilton Head Island. Appreciate the best in oceanfront living and amazing resort amenities from the comfort of this warm and...

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

Hilton Head Tours & Activities

Old Town Bluffton

Hilton Head Helicopter Tours

Book online
$229.00

max_age: 100 description: Experience an exhilarating helicopter tour over Hilton Head and Bluffton that highlights the area's natural beauty and historic sites. Fly over Pinckney Island to look for bald eagles and hawks, sweep across Bluffton’s...

Private Sunset Cruise (Up to 14 Passengers)

Island Head- Hilton Head Harbor

Book online
$549.00 - $699.00

meeting_point: 43 Jenkins Rd, Hilton Head, 29926, South Carolina description: The private sunset cruise is the perfect way to end a day on Hilton Head Island. There is nothing quite like a low country sunset, especially seeing one from the water...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$80.99 - $161.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Private Inshore Charter Fishing aboard Hobo
Book online
$440.00 - $540.00

duration: 3 Hours cancellation_summary: 48 hours meeting_point: Drifter Excursions, 86 Helmsman Way, Palmetto Bay Marina group_size: Licensed for up to 16 passengers; rate includes 6 passengers pricing: - **Two-Hour Charter** - *$440* - Includes 6...

Bike Rental • One Month

Lowsea Bike, Beach and Baby Rental

Book online
$100.00 - $140.00

duration: 30 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...

Baby Gear Rental • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $125.00

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...

Nine Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $295.00

description: Electric Bike Rental Duration 9 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

Beach Cruiser

Hilton Head Helicopter Tours

Book online
$69.00

description: The Beach Cruiser is a helicopter sightseeing trip that flies over the sandy shores of Hilton Head, offering sweeping coastal views. Guests see landmarks and natural scenery from above, including beaches, creeks, and coastal sounds. The...

Trail Rides Experience - Montage Guests

duration: 1.5 hours meeting_point: Longfield Stables Trail Barn min_age: 8 group_size: Up to 5 people description: Embark on an unforgettable experience through the scenic Lowcountry of Palmetto Bluff. Our expertly guided rides take you through...

Baby Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $175.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 5 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

Hilton Head Pedego Electric Bike Tour

duration: 2 hours meeting_point: Hilton Head Island, SC min_age: 16 pricing: $95 per person description: WHAT A GREAT DAY! HELLO FUN!!! what_is_included: There is no better way to experience Hilton Head than on a comfortable seat of a Pedego...

Six Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

description: Electric Bike Rental Duration 6 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

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