Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Family-Friendly Condo with WiFi, Pool, H...

Summary:Island Club 4304The Space:Ideal temperatures and ocean breezes beckon you outdoors at this beachfront rental on Hilton Head Island. With access to multiple shared pools and hot tub, exercise center, and the close by beach, you'll have...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Roomy Two-Story Villa with Two Pools - M...

Summary:Fazio 11The Space:Treat yourself to an memorable hideaway when you stay at this enchanting villa on Hilton Head Island! From strolling on the beach to sampling local cuisine to calming by the shared pool, this striking rental is an ideal...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Breathtaking Ocean Views, Steps to Colig...

Welcome to Your Coastal Retreat at Oceanside Villa 360!This striking villa offers a serene escape with a separate bedroom featuring a comfortable queen-size bed. The completely equipped kitchen seamlessly connects to a combined living and dining...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Fun in the sun Beach access, pools, hot ...

Summary:Hilton Head Resort 3306The Space:NOTICE: Welcome to your ideal hideaway in Hilton Head, SC! This striking 3rd-floor condo offers a convenient 8-min. walk to the beach, making it an ideal getaway for families and beach lovers alike. Savor...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming third-floor condo- private balc...

Summary:Sands Village B 3BThe Space:Beachy, bright, and handsomely refreshed, this inviting two-bedroom condo is the ideal setting for your next Hilton Head Island hideaway. Thoughtfully designed with modern furnishings and an open layout, the space...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
3rd Floor Villa with Private Washer & Dr...

Summary:Fiddlers Cove 6JThe Space:Feel the ultimate beach hideaway at this beautiful condo in Hilton Head, SC. Located near the ocean, this family-friendly getaway offers a plethora of amenities to ensure a comfortable and enchanting stay. This...

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

Hilton Head Tours & Activities

Bike Rental • Five Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Rent Bikes and Gear Accessories for your vacation! Duration 5 Days About All bike rentals include: - Free Delivery & Pickup - Free Basket - Free Lock Bike Options: **Adult Cruiser 26"** ![Adult Cruiser...

Daily Clinics

Palmetto Dunes Golf Academy

Book online
$50.00

meeting_point: Arthur Hills golf course description: Learn something new every day! Duration 50 minutes About The Academy presents a daily golf clinic at the Arthur Hills Golf Course, featuring special instruction on the stroke of the day...

One Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$20.00 - $100.00

description: Rent with us! Duration 7 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 attachments

Archery Tag

Jeffery Archery

Book online
$225.00 - $375.00

duration: 1 or 2 Hour Parties description: Experience the thrill of dodgeball combined with archery in our action-packed Archery Tag events. Using lightweight bows, foam-tipped arrows, and inflatable bunkers, players compete in fast-paced team games...

A.C.E. Basin & Monkey Island Tour

Beaufort Dolphin Adventures

Book online
$372.64

duration: 2 Hours cancellation_summary: Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances...

Playing Lesson

Palmetto Dunes Golf Academy

description: Duration & Rates - 2 hours - Price varies. Please call to get pricing. About Play with the Pro & learn as you go. Videos, photos & instruction notes are included. - When: Seasonal - by appointment only & course availability ...

Lowcountry Mini Shoot

Island Life HH Photography

Book online
$199.95 - $249.95

duration: 10–15 minutes cancellation_summary: Full refund if weather forces cancellation and no mutually available reschedule; otherwise weather-dependent rescheduling. meeting_point: Jarvis Creek Park, 100 Jarvis Park Rd, Hilton Head Island...

Learn to Sail Adventure

Otter Sailing Adventures LLC

Book online
$600.00

duration: 3.5 hours or more group_size: maximum of 6 description: Duration 3.5 hours About Experience the thrill of learning to sail on our Catalina 275 Sport, the perfect boat for learning keel boat sailing for the first time or honing your...

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** ...

2 Week Rental (Walk Up)

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks cancellation_summary: 24 Hours in advance meeting_point: Hilton Head Island, SC description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book...

As Seen on TV: Greenville Culinary Highlights

duration: 3.5 Hours meeting_point: 170 Riverplace, Greenville, SC 29601 description: In recent years, Greenville's culinary scene has had increasing visibility and notoriety on the national stage. Multiple James Beard nominations in a year, Michelin...

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...

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