Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

3 Bed/3 Bath Villa on the Fourth Floor w...

Discover the beauty of Hilton Head Island with beautiful ocean and beach vistas from the private balcony of one of our oceanfront villas. Choose from cavernous 1, 2, or 3-bedroom villas in a variety of floor plans, each offering a comfortable...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
lofted villa with private deck, streamin...

Sealoft 2055Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'A lofted villa in a canopy of trees where the windows are the walls is waiting to welcome you to...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Pool view condo with screened in patio, ...

Windward Village 120Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your attractively decorated condo located in the serene Shipyard Plantation of...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
11 Dinghy Oceanfront W/ Pool/Spa & Eleva...
4.9
(41)

Don't miss out on this Awesome Oceanfront home with many amenities the island of Hilton Head that has great all year-round weather and known for its huge, beautiful beaches where early morning walks and bicycle rides is the thinks to do to start the...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 18
Incredible villa with pool and tennis ac...

Evian 209Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This rental is a elegant, newly updated villa located in the heart of Shipyard Plantation. This...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Charming condo near the beach with outdo...

Forest Beach Villas 409Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to gorgeous Hilton Head Island at this fourth-floor condo just steps from...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Two Day Chair or Umbrella Rental

Hilton Head Outfitters - Bike Rental

Book online
$29.99

description: The durable and comfortable reclining Hilton Head Outfitters beach chair rentals are made of light-weight aluminum with backpack straps for easy transportation. They can be rented individually or as a package.

Kids Summer Splatter-Paint Camps

Color Me Greenville

Book online
$225.00

duration: 30 mins meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: Kids Summer Splatter-Paint Camps

Signature Catering & Events by SERG x Island Head

duration: 2 Hours meeting_point: 18 Simmons Road at Broad Creek Marina min_age: 21 description: One night only — sip your way through a hand-selected wine tasting paired with bites from Signature Catering & Events by SERG. All aboard our luxury...

Lowcountry Marsh Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Weather cancellations rescheduled when possible; full refund if reschedule cannot be arranged. meeting_point: 59 Shelter Cove Lane, Hilton Head Island, SC description: Join us along the Lowcountry...

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

description: *Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* ___________________________________ Rates are per private charter **2 Hours** - $375*-Only Recommended for Small Children* **3 Hours** ...

Private Dolphin Discovery Tour - One Hour

Island Life Rentals and Tours

Book online
$35.00 - $250.00

duration: 1 Hour group_size: 12 - 14 Max description: See dolphins up close! Now you can enjoy the thrill of a small boat expedition for nearly the same cost as the big boat "bus tour". Join Island Life for a great introductory cruise through the...

Phone Dry Bag

Lowcountry Watersports

Book online
$12.95

Fall Speaker Series: Legends & Luminaries of Hilton Head Island

duration: 1.5 hrs 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 the Coastal Discovery Museum as we commemorate our 40th...

Private Family Or Group Fishing Trip Aboard The Drifter

duration: 3 Hours cancellation_summary: 72 Hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way group_size: 32 people pricing: The Private Family or Group Fishing Trip Aboard the Drifter has a set price of $995 for a group size of 16 people or...

Private Lesson with Clark Sinclair

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

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 especially enjoys using video analysis as a teaching...

Salt Marsh Discovery

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

meeting_point: Coastal Discovery Museum, 70 Honey Horn Drive, Hilton Head Island, SC 29926 description: *Learn from an expert why the Salt Marsh is so vital to the ecosystem!* ___________________________________ Duration 1 hour and 30 minutes...

Three Week Electric Bike Rental

duration: 21 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

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