Hilton Head, SC Vacations

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Featured Vacation Rentals

Marriott Grande Ocean Hilton Head Tennis...

Ocean View luxury 5 Star Resort on the Ocean in Sea Pines Plantation Hilton Head. Two Bedroom and two bath unit that sleeps eight. King-size bed in the Master and two queen beds in the second bedroom. Queen sleeper couch in the living room. ...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beach-view condo in oceanfront complex w...

Breakers 223Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Dreaming of beach days just outside your door? Welcome to your ideal Hilton Head Island escape...

  • Hilton Head
  • 2 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beach Villa - Close to all the action! B...

New kitchen complete with granite countertops. Freshly painted and new floor throughout.Bedroom 1 - Queen Bed with complete bath, Bedroom 2 - twin over full bunk beds with complete bath. Villa has laundry facilities, outdoor patio with a grille and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
44 Bradley Beach, Close to Beach, Large ...

**New Bonus Room Off of the Pool and Updated Bathrooms!!**44 Bradley Beach is a 6 Bedroom, 4.5 Bathroom family vacation home that sleeps 15 and has a huge 16' x 32' pool, and features an outdoor fire pit ideal for a nighttime hosting around the pool...

  • Hilton Head
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 15
Oceanfront Luxury – Newly Renovated 2-...

Step into this captivating top-floor, completely transformed villa and be greeted by the mesmerizing ocean view. Be one of the first guests to experience the ultimate in coastal sophistication. This impressive property blends modern luxury with...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Second-floor condo with pool access, bal...

Sands Village A2EOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your ideal hideaway in Hilton Head, SC! This beautiful corner condo is just a...

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

Hilton Head Tours & Activities

Six Day Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

description: Electric Bike Rental Duration 6 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

Public Sunset Sail on Knot The Office

Anchors Away Sailing Charters

Book online
$110.00

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...

HH Seafood Festival: Private Fireworks Cruise: Up to 6 guests

description: Enjoy an evening on a private sunset dolphin cruise from Shelter Cove Marina and watch the firework display from the best seat in the house. Six, Twelve and Sixteen passenger boats available. Departing Saturday February 26th from ...

Two Day Schools

Palmetto Dunes Golf Academy

Book online
$750.00

Duration & Rates - 2 Days, 3 hours of instruction per day - $750 per student About The small group 4:1 student:teacher ratio promotes important quality attention. Skill levels can be mixed and the instructor is able to meet the unique needs of...

Private Family Or Group Fishing Trip Aboard The Drifter

duration: 3 Hours cancellation_summary: 72 Hours meeting_point: Palmetto Bay Marina, 86 Helmsman Way group_size: 32 people pricing: The Private Family or Group Fishing Trip Aboard the Drifter has a set price of $995 for a group size of 16 people or...

Jet Ski Rental

Wateree Marina

Book online
$125.00 - $800.00

meeting_point: Wateree Marina description: Half or Full Day Jet Ski Rentals Know Before You Go - All jet skis may accommodate two passengers total. - All renter's/driver's must be 21 years or older. - All passengers must be 16 years or older. ...

Daufuskie Trip

Flip Flop Charters

Book online
$725.00

Come explore the island! Duration 3 hours About Tucked between Hilton Head and Savannah is Daufuskie Island. With no bridges it is only accessible by boat. On the island are restaurants, golf courses, a distillery, and plenty of history.

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Bike Rental • Two Day

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $80.00

duration: 2 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Dolphin Cruise

Carolina Breeze Charters

Book online
$275.00 - $350.00

duration: 2 hours meeting_point: Broad Creek Marina, 18 Simmons Rd, Hilton Head Island SC 29926 group_size: Maximum 6 people description: Discover the best of beautiful Hilton Head Island, SC aboard the Carolina Breeze, a 31-foot yacht-class vessel...

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: Hibachi Dinner Cruise Experience an...

22' Pontoon Rental

H2O Sports

Book online
$325.00 - $750.00

duration: 2-6 hour rentals cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Meet at H20 Sports booth, conveniently located next to the lighthouse and departure dock! group_size: Boat holds 11...

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