Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanside 1st floor villa in Palmetto Du...

This is your happy place! Elegant ocean side villa a short walk to the beach!HILTON HEAD ISLAND. Wendover Dunes is a handsome ocean-side villa complex that is just a short walk to the beach. Located next to the Barrington Enclave in Palmetto Dunes...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Ocean-View Treetop Escape w/ Fire Pit!

Plan your next hideaway for a stay on the sandy shores of Hilton Head Island when you book this 2-bedroom, 2-bathroom vacation rental home. The treetop home features a private setting with handsome ocean vistas that can be seen from inside and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Fifth Floor Villamare unit with lots of ...

Welcome to this attractively refreshed fifth-floor, two-bedroom Villamare condo with ocean vistas, located within the acclaimed Palmetto Dunes Oceanfront Resort. Recently refreshed throughout 2026, this inviting getaway features new living room and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Recently Updated Resort Villa with WiFi ...

Summary:Nighttime Heron 18The Space:This alluring freestanding villa is surrounded by the lush landscape of the Sea Pines Resort and is a short walk away from the sandy white beaches that make Hilton Head Island a premier vacation destination...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3 Bedroom situated on the Robert Trent J...

This gorgeously decorated, freshly remodeled 3-bedroom villa offers a modern and opulent touch, ideally located within the esteemed Palmetto Dunes Oceanfront Resort. With vistas of the acclaimed Robert Trent Jones Golf Course, this villa is a...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Family Friendly Condo, outdoor indoor po...

Summary:Hilton Head Resort 1108The Space:NOTICE:Welcome to a charmingly refreshed two-bedroom, two-bath condo located in the serene Hilton Head Resort. This peaceful getaway offers gorgeous balcony vistas overlooking the marsh, with the beach just a...

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

Hilton Head Tours & Activities

Shark Fishing Aboard the Drifter
Book online
$62.00 - $72.00

duration: 30 minutes (travel time) cancellation_summary: 48 hours meeting_point: 86 Helmsman Way. Please meet at the flag pole at the right side of the marina. group_size: Number of passengers is limited pricing: * Adults: $72 * Children 12 and...

Half Day Flats Fishing (4 Hrs)

Green Heron Adventures

Book online
$550.00

meeting_point: Beaufort and Hilton Head/Bluffton, SC description: Duration 4 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target...

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

description: Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of...

Gift Card

Wateree Marina

description: Purchase the perfect gift: a gift card with a value of your choosing!

One Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$259.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** **All eBike rentals include 1 lock for every bike.** Our e-bikes are a fun and easy...

Two Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$27.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

Bonjour Private Charter

BC2 - Island Head

Book online
$550.00 - $5,500.00

duration: 1-10 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 35 People description: Bonjour – Hilton Head’s Premier Charter Boat Step aboard Bonjour, Hilton Head’s newest and most luxurious charter boat, built...

Kayak Rentals (Please call if unsure about booking a Guided Tour versus a Kayak Rental)

description: Kayak unguided if you have kayaking experience. We will go over the area with you, tell you about the dolphins favorite spots to hang out and answer any questions that a you have before departure. Of course our guided tours are...

Yamaha AR195 Jet Boat

Timberlake Marina

Book online
$300.00 - $1,500.00

duration: 8.5 Hours min_age: 23 group_size: Maximum capacity is 8 people or 1,280 lbs. description: Sporty, Supercharged Jet Boat for cruising Lake Murray, Tubing, watersports and family fun! No Propeller, Excellent Swim Platform, 250 HP There’s...

Sunset Dolphin Cruise

Island Life Rentals and Tours

Book online
$55.00 - $660.00

duration: 2 Hours group_size: 12 - 14 Max description: What could be more peaceful and romantic than a beautiful sunset cruise on the calm evening waters around Hilton Head Island. Share this experience with your loved ones and create memories to...

PB Palmetto Bluff Shrimping Excursion

meeting_point: Palmetto Bluff description: Description Fall in the Lowcountry is shrimp season. Come and join us for what the locals consider a true right of passage. Learn how to throw a cast net for shrimp the way local watermen have for...

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