Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Wonderful Three Bedroom Home on the 11-M...

Come savor this charmingly refreshed private home with its lagoon vistas and enormous pool. Upon entering the home you are greeted by the broad Living and Dining Areas. The Living Room features a wall of windows with a slider to your huge private...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Marriott's Barony Beach Club Oceanside/G...

Live your best life at Marriott's Barony Beach Club. Perfectly located on the striking oceanfront of Hilton Head Island, South Carolina, our vacation rental beach resort offers the ideal backdrop for creating a lifetime of memories. Feel at home in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Large Second Row Home in the Heart of Pa...

You'll be glad you chose this cavernous and handsome second-row home in Hilton Head Island's esteemed Palmetto Dunes Oceanfront Resort! With six bedrooms and six and a half bathrooms, this home is ideal for sizable families or groups looking to...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Spacious & elegant family condo with poo...

Summary:Links 14BThe Space:This freshly refreshed 1,700-square-foot villa is just a 15-min. walk to a handsome beach park and a 5-min. walk to the neighborhood’s private pool. Located at the end of a peaceful street, the villa features a backyard...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Lovely Condo with Shared Pool & Tennis D...

Summary:Greens 203The Space:Immerse yourself in the lush woodland setting of Greens 203, a attractively located condo in Shipyard Plantation on Hilton Head Island. A few steps to get inside and you'll find a great room with vaulted ceilings, a...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Upgraded condo on waterfront with pool, ...

Summary:Island Club 5202The Space:With a spectacular direct ocean view, this condo has all of the amenities you'll want at your next stay at Hilton Head. Recent renovations create a comfortable and pristine space for the entire group to savor...

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

Hilton Head Tours & Activities

Memberships

The South Carolina Railroad Museum

Book online
$20.00 - $400.00

pricing: - **Family (4 People) Membership:** $50.00 - **Individual Membership:** $30.00 - **Senior (62+) Membership:** $25.00 description: When you join as a member of the South Carolina Railroad Museum, you’re ensuring our museum and railway are...

1.5 Hour Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$53.99 - $69.99

description: Single Kayak 1.5 Hour Rental: $43.99 ________________________________ Double Kayaks or Canoes 1.5 Hour Rental: $56.99 __________ Triple Canoe 1.5 Hour Rental: $69.99

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Hilton Head Yacht Cruise

Salt Shaker Charter LLC

Book online
$3,750.00 - $6,600.00

duration: 4 - 8 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Your Cruise, Completely Customized! At Salt Shaker Charter, every cruise is tailored to you. From intimate getaways to...

Shark Fishing Charter

Gone Fishing HHI

Book online
$400.00 - $700.00

description: Fish like a local! Duration & Rates **2 Hour Charter** - *$375* **3 Hour Charter** - *$475* **4 Hour Charter** - *$575* About The two hour trip is great for groups with young kids, beginners, or groups just looking to get out for...

HHI: Tales Through Time

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about island history from an expert!* ___________________________________ Duration 1 Hour ___________________________________ About Hilton Head Island has been visited and inhabited for over 4,000 years—from the...

Cooler and Ice

Lowcountry Watersports

Book online
$15.00

Private Lesson with Clark Sinclair

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

meeting_point: George Fazio Course description: About Clark Sinclair, Director of Golf Clark Sinclair has been a member of the Palmetto Dunes staff since 1983 and has been teaching since 1986. He is a graduate of Presbyterian College. Clark...

Private Boat Rental w/ Captain

Dolphin Discoveries Hilton Head

Book online
$225.00 - $350.00

duration: 1.75 - 4 Hours cancellation_summary: 48 hours - No Questions Asked meeting_point: Broad Creek Marina - End of wooden pier, at sign, over the water. group_size: Up to 8 recommend. If more please call. accessibility: Boats take 2 steps from...

All Day Kayak Rentals

Crooked Creek Kayaks

Book online
$80.00 - $100.00

duration: 8 Hours description: Unguided access begins with personalized, concierge-style recommendations designed to help you move with Jarvis Creek’s ever-changing tidal currents. Before you launch, our team will walk you through ideal routes...

Beach Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Everything you need for a fun and comfortable day at the beach! Duration 4 Days About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than...

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...

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