Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Beachwalk at Shipyard Pool, Golf & Tenni...

Summary:Beachwalk 206The Space:Highlighted by a prime location and a host of on-site amenities, island dreams come true at this 2BR/2BA Shipyard Plantation hideaway. Perks include a sleek kitchen and a roomy and private deck with alfresco dining...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
104 Barrington Arms 3 Bedroom 3 Bath

Welcome to this striking three bedroom oceanfront condominium, ideal for families seeking a opulent and cavernous hideaway. This sizable condo offers comfort, style, and gorgeous ocean vistas.The completely equipped kitchen features sleek granite...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Charming 3 bedroom 3 1/2 bath home in be...

Summary:Isle of PinesThe Space:This striking three-bedroom three and a half bathroom home in the Sea Pines plantation is the ideal choice for entertainment and relaxation. Featuring many new updates to the full kitchen, bathrooms, ceiling and floor...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Updated, waterfront condo with amazing l...

Summary:Fairway Lane 102The Space:Located just a short distance from the beach in Sea Pines, this freshly refreshed condo is a warm and inviting, family-friendly hideaway boasting marvelous amenities both inside and out. Upgrades include new windows...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Schooner Court 705

Summary:Harbour Town hideaway with breathtaking balcony, water vistas just steps from the lighthouseThe Space:Make your next vacation stand out when you stay in this impressive Harbour Town condo. With striking vistas from the balcony, spend a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
First Floor, Oceanfront Condo with Free ...

Summary:Villamare 1103The Space:This coastal-themed and freshly remodeled condo in Palmetto Dunes offers striking ocean and pool vistas! The first-floor location will make this condo accessible for everybody! Gain access to the balconies from both...

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

Hilton Head Tours & Activities

Glow in the Dark Splatter Session

Color Me Greenville

Book online
$55.00

duration: 30 Mins Splatter Paint Session meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: $55 per person for Glow in the Dark Splatter Session. description: It’s your invite to light up the night...

Dolphins & Donuts (Small Group)

Lowcountry Watersports

Book online
$15.00 - $59.00

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 max_age: 99 group_size: 1- 6...

Jet Ski Rental

Timberlake Marina

Book online
$250.00 - $700.00

duration: 4.5 or 8.5 Hours min_age: 23 group_size: Maximum capacity is 2 people description: There’s nothing quite like a day on Lake Murray—wide open water, sunshine reflecting off the surface, and miles of shoreline waiting to be explored. At...

North Pole Express

The South Carolina Railroad Museum

Book online
$17.00 - $22.00

duration: 1.5 - 2 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: Come visit Santa on our annual holiday ride. Santa walks through the train and comes to you. No lines! The ride lasts about 90 - 120 minutes, or...

Phone Dry Bag

Lowcountry Watersports

Book online
$12.95

Cinco de Mayo…..The YoCo LoCo way!

description: About Hop aboard for a fiesta on wheels! We will kick this tour off at The Print Shop, Fort Mill. Enjoy great beer and beautiful outdoor seating. We will cruise over to Tony’s Cantina in Riverwalk to enjoy margaritas and delicious...

Three Day Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$15.00 - $60.00

duration: 3 day bike rentals cancellation_summary: NO REFUNDS OR RAINCHECKS meeting_point: your address description: Bike rentals for a three day period. (Example: you rent the bikes on monday, they are due back thursday morning) what_is_included...

Private Dolphin Encounter - Two Hour

Island Life Rentals and Tours

Book online
$45.00 - $540.00

duration: 2 Hours group_size: 12 - 14 Max description: Every trip is a unique experience. Dolphins abound in the Hilton Head waters, and you'll enjoy the thrill of seeing them up close aboard Island Life's safe, comfortable boats. Our experienced...

Sunset Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

description: Stunning Sunset Views About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Stunning sunset views over...

Six Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

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...

Bunch Bike - Family E-Bike Fun!

Pedego Electric Bikes Greenville

Book online
$109.00

duration: 6 to 8 Hours meeting_point: Pedego Electric Bikes Greenville. Located at Hampton Station - 1320 Hampton Ave Ext. STE 11A Greenville, SC 29601 description: Experience family fun like never before! ???? Experience the Thrill of...

Surfboard Rental

Forest Beach Surf & Cycle

Book online
$25.00 - $125.00

description: Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island surf rentals!

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