Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Oceanfront Condo with Shared Pool, Hot T...

Summary:Island Club 1101The Space:Kick back and relax in the appealing amenities of this two-bedroom condo with peekaboo vistas of the beach in Hilton Head. The condo is decorated to inspire comfort and relaxation, but when you are ready to venture...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Island condo with beach access and balco...

Summary:Villamare 2319The Space:Savor all the amenities of home at this Palmetto Heaven. The chic furnishings and tasteful decor create a pleasant ambiance for a group of friends or the entire family. with a full kitchen, mealtimes will be a breeze...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lagoon front, 3 story condo w balcony & ...

Summary:Seascape Villas 3207The Space:Feel the best of Hilton Head Island from this 3 story impressive condo just 0.7 miles from Coligny Beach Park. With a prime location near trendy attractions like The Boardroom and Harbour Town Golf Links...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
NEW Hilton Head Beach & Tennis Resort Bu...

Welcome to A STEP AWAY—your calming oceanside hideaway where every moment feels kissed by sunshine and sea breeze. Tucked away on the first floor of Ocean Villa B at Hilton Head Island Beach & Tennis Resort, this cozily designed one-bedroom condo...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Two King Bed Suites, Dog-friendly gem wi...

Summary:Eagle WatchThe Space:This four-bedroom, three-and-a-half bath golf home offers ideal comfort for your vacation. Eagle Watch makes calming painless thanks to its private pool, jetted tub, recreation room, outdoor grille, and accessibility to...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
Direct Ocean View Condo with balcony, po...

Summary:HH Beach & Tennis 302ARThe Space:**Need to Know Notes**Admiral's Row Sprinkler ProjectAnticipated Start date: 1/15/2026Potential Construction Traffic and NoiseThere will be additional dumpsters and debris on property at this time.Timeline...

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

Hilton Head Tours & Activities

Beach Cruiser

Hilton Head Helicopter Tours

Book online
$69.00

description: The Beach Cruiser is a helicopter sightseeing trip that flies over the sandy shores of Hilton Head, offering sweeping coastal views. Guests see landmarks and natural scenery from above, including beaches, creeks, and coastal sounds. The...

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...

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** ...

9 Day Rental

Island Life Rentals and Tours

Book online
$39.00 - $275.00

duration: 9 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Two Day Surfboard / Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$69.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Rate Two Day Rental: $69.99 *NOTICE: The minimum age allowed out on the lagoon is 5 years old!* _______________ Duration 2 Days

PB Palmetto Bluff Biking The Bluff

duration: 2 Hours meeting_point: Palmetto Bluff, Bluffton pricing: Starting at $70 per Guest description: *Palmetto Bluff is a bicyclists paradise!* Take a bike tour through Palmetto Bluff’s 20,000 acres, which include historic architecture...

Private Sunset Sail and Dolphin Watch on Knot The Office
Book online
$350.00 - $465.00

duration: 2–2.5 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 people accessibility: Limited Handicap accessibility, Please call us to ensure...

Daufuskie Island History & Artisans Excursion

meeting_point: Hilton Head Island, SC description: *Catch a glimpse into Lowcountry history!* --- Description This 4.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of...

Monkey Safari

Hilton Head Helicopter Tours

Book online
$369.00

description: Fly north from Hilton Head toward Morgan Island (Monkey Island) for scenic aerial views of the Lowcountry coastline and abundant wildlife. Keep an eye out from the helicopter for dolphins, sharks, and sea turtles as your experienced...

C - PB Nature Walk

meeting_point: Palmetto Bluff, Bluffton description: MAY RIVER WALK AT THE BLUFF Palmetto Bluff is a nature lovers paradise. This interpretive tour will take a loop route that will mix forested paths as well as paths along the May River all at...

10 Day Rental

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Six Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$800.00

description: Duration 6 Hours ___________________________________ About Redfish, Trout, Blackdrum, Sheepshead, Jack Crevalle, Tarpon, Spanish Mackerel, Cobia, Sharks! 6hrs gives us time to target a couple different species, more fishing time...

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