Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Stunning home lagoon views and close to ...

Summary:Serene SpartinaThe Space:Located in the heart of the esteemed Sea Pines Resort in Hilton Head, SC, this roomy home offers a sought-after location with a shared neighborhood pool and tennis courts a short drive away. With an open floor plan...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Coastal chic condo- Pools, Tennis Court,...

Summary:Hilton Head Resort 2301The Space:NOTICE: The hot water tub is down until further notice. Thank you for understanding.Feel coastal living at its best in this striking third-floor condo in Hilton Head, SC. Ideal for remote working, the bedroom...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Beachside Condo with Shared Pool & Priva...

Summary:Breakers 128The Space:Unwind on your private deck and savor the coastal breeze at this inviting beachside getaway. Take in ocean vistas from the balcony as you plan your day, whether it’s filled with adventure or laid-back relaxation. The...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Oceanfront condo w/free WiFi, balcony, s...

Sea Cloisters 305Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sea Cloisters 305 is a impressive, two-bedroom, two-bathroom, oceanfront condo in the complex...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
309 Ocean Dunes - Amazing Ocean Front Be...

Savor unbelievable ocean vistas and sunrises during the day and ultra-clear starlit nights, right from the deck of this attractively maintained beach condo. This is full direct and up close 180-degree 3rd floor view of the entire beach and ocean...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Expansive Private Oceanfront Home with V...

Fall in appreciate with this broad oceanfront home located on the Atlantic Ocean in pretty Palmetto Dunes Oceanfront Resort! As you enter you are welcomed by a grandiose staircase and wood floors leading to the kitchen, dining and living areas. ...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Two Month Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$160.00 - $800.00

description: Rent with us! Duration 60 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and...

Bar Crawl

Flip Flop Charters

Book online
$625.00 - $750.00

description: Beautiful Scenery Duration - 3 hours - 4 hours About If you’re looking for some adult fun, there is no shortage of waterfront bars in our area. We’d love to take you to some of our favorites or let you pick the itinerary....

Three Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$660.00

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...

3 Hour Private Spring Jocassee Boat Tour

description: Private 3hr Spring Tour on Beautiful Lake Jocassee! Rates - Private Charter (includes up to 6 people): $350 ***$50 for each additional person (up to 10 total passengers)*** About Boat Tour includes all major waterfalls...

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...

New Exhibition: Opening Reception

Coastal Discovery Museum Hilton Head

duration: 5:00PM - 7:00PM description: The Coastal Discovery Museum, a Smithsonian Affiliate, opens a retrospective exhibition, “It's Thursday! Artists of the Round Table,” on November 12, celebrating 15 prominent local artists who gathered...

July 4th Fireworks Cruise
Book online
$65.00 - $95.00

description: *Get the best seat in the house for the Independence Day fireworks!* --- > Prices >- **Adults:** $145 >- ** All Children:** $95 (12 and under) --- Description Book this cruise early, it is extremely popular! Incorporates a 2...

PVT Shark Tooth 6p

description: Discover Shark Tooth Island! ___ Description Enjoy a boat cruise from Hilton Head Island through the back waterways to Shark Tooth Island (near Savannah, Georgia) where you can hunt for shells, shark teeth and other ocean...

Private Morning Sail and Dolphin watch on Knot The Office
Book online
$315.00 - $395.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 passengers accessibility: Limited Handicap accessibility, Please call us to ensure we...

Wine Blending Class

Kennington Family Winery

Book online
$75.00

duration: 2 Hours min_age: 21 group_size: Maximum 8 Guests description: Blending class- test out different blends of 3 of our Italian wines to determine your favorite ratio. Led by our wine maker or owner, this class will take you behind the scenes...

Round Trip To Downtown CHS

Daniel Island Ferry

Book online
$10.00 - $50.00

duration: 30 Minutes cancellation_summary: 48 Hours before departure - refund or credit available. 24-28 hours before departure - credit for a future trip. Inside of 24 hours - no refund or credit. meeting_point: 1 river landing drive, Daniel...

4 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$24.00 - $175.00

duration: 4 Days cancellation_summary: 24 Hours in advance description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours...

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