Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

2 Min Walk 2 Beach Pickleball Golf Tenni...

One of the very best located properties in Hilton Head. December and January great for beach activities: golf, tennis, pickleball. Savor our private heated pool and spa. A great last min. gift for Christmas is a vacation in Hilton Head.Book...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Comfortable Townhome with WiFi, Screened...

Tennismaster 1101Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Please note the Tennismaster pool is closed as of 9/25/2025. Renovations will begin...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Beach Blossom - PET FRIENDLY PRIVATE HOM...

Stunning 3 Bedroom 2 Bathroom home located off Folly Field Rd. Beach Blossom has just been completely refreshed and designer decorated. Upon entry you will be greeted by a completely furnished living room with vinyl floor throughout, and a mounted...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Large Three Bedroom Villa Overlooking th...

You are going to appreciate staying in this very well kept three bedroom Inverness villa. This villa has been generously decorated throughout with the beach in mind. The entirely equipped kitchen with bespoke cabinetry has everything you will need...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Second row to the ocean - 5 bedroom newl...

2nd Row Ocean! 5 Bedrooms, 4 Full baths, 2,500sq.ft. Next to Sea Pines Ocean gate.You will definitely fall in adore with this beautiful South Forest Beach home! The property is located right outside the Sea Pines ocean gate and is second row to the...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
SerenityByTheSea-Couples Retreat-King,Bi...

Treat yourself to the ultimate Hilton Head escape in this charmingly decorated villa with marvelous ocean vistas—just steps from the sand and walking distance to the island’s top eateries, stores, and bars.Unwind in the king bedroom, refresh in...

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

Hilton Head Tours & Activities

Saint Helena Sunset Sail

Otter Sailing Adventures LLC

Book online
$375.00

There's nothing like experiencing the magic of a sunset under sail in the beauty of the St Helena sound Duration 2 hours About Private Sailing Charter - Price Per Group (up to 6) There's nothing like experiencing the magic of a sunset...

4.5 Hour Deep Sea Fishing Aboard the Drifter
Book online
$65.00 - $1,000.00

*Fishing for the whole family on Hilton Head Island!* ___________________________________ Rates - **4.5 Hour Deep Sea Fishing:** - $75 ___________________________________ About - The Drifter is a 60-foot long party fishing boat that has...

Fireworks & Nature Boat Cruise

*Get the best seat in the house for the Shelter Cove Harbour Festival fireworks!* --- > Rates >- **Adults:** $65 >- **Children:** $45 (12 and under) >- **Small Children:** $40 (under 2) Description Book this cruise early, it is extremely...

Glow Splatter Painting AND Cake Decorating
Book online
$45.00 - $425.00

duration: 2.5 hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max pricing: Prices start at $600 description: You asked, we listened!! Now you can book a party for Cake Decorating and Splatter Painting!...

8 Hour Fishing Charter

Awesome Adventure Charters

Book online
$1,220.00

The Ultimate Trip for Hardcore Fishing enthusiasts. The More Time Spent on the Water, the Better Your Chances of Catching “Big Jesse”! Duration 8 Hours About Whether going for that trophy fish, pursuing world-class tarpon in the ocean, or...

Private Lesson with Edward Sires

Palmetto Dunes Golf Academy

Book online
$110.00 - $550.00

About Edward Sires A Charleston, S.C., native, Edward Sires caddied for Ryder Cup Captain Tom Lehman in 1982 and 1983. He earned a Class A certificate from the PGA in 1997 and has taught the James Island High School Golf Team from 2002 to 2006. He...

Stand Up Paddle Board Rental

Forest Beach Surf & Cycle

Book online
$60.00 - $200.00

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

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

*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** - $475 **4 Hours*...

Lake Keowee - Jet Ski Rental

Captain Cams Watersports

Book online
$275.00 - $350.00

duration: 4-7 Hours meeting_point: 757 Keowee Baptist Church Road Six Mile, SC 29682 min_age: 25 group_size: Up to 6 People description: We run Yamaha VX models. These are very comfortable jet skis that will go about 45 mph depending on the weight...

Private Party

Palmetto Axes

Get the joint all to Yourself! About *Ages 12+ • Up to 36 People* All the fun for you and as many people as the fire marshal will let in the place. Book 2 plus hours and save even more! - Bring in your own food - Maximum of 36 people per...

Solaris - Destination Charter (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Customize your luxurious destination charter aboard Solaris today! **Our private charters accommodate up to ten passengers, ensuring an intimate...

Private Sunrise Cruise

Island Head - Broad Creek

Book online
$325.00

duration: 1.5 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC group_size: Up to 14 Passengers pricing: *All Ages, Up to 14...

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