Hilton Head, SC Vacations

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Featured Vacation Rentals

6 Terra Bella, Oceanfront, Elevator, Pri...

6 Terra Bella Trace, Hilton Head Island is located between the salt marsh and the Atlantic Ocean, 6 Terra Bella Trace is a beach lover's heaven. This magnificant property features 6 bedrooms and 8 bathrooms. The chef's kitchen features...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 20
Lovely house with gourmet kitchen, scree...

Summary:Black SkimmerThe Space:This property in the Sea Pines development sits among the natural beauty of Hilton Head Island's palmetto and oak trees. Walking paths and boardwalks give you fast and simple access to the community's beach area.After...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 13
New to the Rental Market!

5201 Hampton Place is a gorgeously decorated one bedroom and two bath villa. It is located on the 2nd floor with a striking ocean view looking over lush greenery.Upon entering the villa, you will immediately notice the unique white onyx floors and...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2
Freshly Updated Throughout!

Savor the best of Palmetto Dunes Oceanfront Resort on Hilton Head Island from this roomy 3-bedroom, 2.5-bath vacation rental overlooking the resort’s spectacular 11-mile lagoon system. Set in one of the island’s most sought-after communities...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Serene Oceanfront Villa with WiFi, Pool,...

Summary:Island Club 2201The Space:Charming ocean vistas along with a shining pool complex and multiple tennis courts are among the many perks of this remodeled, oceanfront Island Club condo.While the local vegetation surrounding the Island Club...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 7
Oceanfront Condo with Shared Pool, Hot T...

Summary:Island Club 1101The Space:Kick back and relax in the striking 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

Hilton Head Tours & Activities

DI 6 Hour Ultimate Lowcountry Day

meeting_point: Daufuskie Island, SC description: *Customized adventures are the best way to see and do the Lowcountry!* --- Description Designed for the family or small group interested in experiencing an authentic day in coastal South...

Nine Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$70.74 - $168.39

description: Enjoy miles and miles of scenic bike paths Duration 9 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

2 Week Rental

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks 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...

Sunrise Beach Photography

Island Life HH Photography

Book online
$225.00 - $775.00

duration: Up to 60 minutes cancellation_summary: Full refund if we cancel due to weather; no refund or discount for late arrival meeting_point: 55 Starfish Dr, Hilton Head Island, SC 29928 description: Get your photo taken on the beautiful Hilton...

One Month Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$875.00

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...

Little Swingers

Palmetto Dunes Golf Academy

Book online
$50.00

meeting_point: Robert Trent Jones golf course min_age: 3 max_age: 7 description: Duration & Rates - 50 minutes - $50 per student Little Swingers (offered seasonally) Sundays 10AM - 10:50AM Tuesdays 2:00PM - 2:50PM June1st-August 31st Learn...

Bike Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

duration: 7 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: Confirmation will include your lock combination in addition to delivery and pick up...

One Week 2 Chairs and 1 Umbrella Package

Hilton Head Outfitters - Bike Rental

Book online
$79.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Umbrellas include a sand spike for easy set up at the beach. The durable and comfortable reclining Hilton Head Outfitters beach chair...

Adrenaline Package

Hilton Head Helicopter Tours

Book online
$100.00

pricing: $100 + Taxes/Fees description: Crank up the thrill and elevate your helicopter tour to the ultimate adventure with our doorless experience! Soar through breathtaking landscapes with the wind in your hair and unobstructed views that will...

HH Seafood Festival: Ohana Fireworks Cruise

description: A special cruise on the luxury power catamaran, Ohana. This leisurely sunset dolphin cruise will end with the best seat in the house for the fireworks show! Departing Saturday, February 26th 5-7pm $115 per person (includes Kettle One...

Sunset & Fireworks Tour

duration: 2.5 hours cancellation_summary: All reservations are subject to our 48 hour cancellation policy! group_size: Up to 12 people description: Experience the Magic of Summer Nights! Every Tuesday, Harbour Fest lights up the sky -- and there's...

Seasonal Fireworks Cruise

Flip Flop Charters

Book online
$775.00

description: Watch fireworks at Shelter Cove! Duration 3 hours About From June to August we offer a weekly cruise to watch the fireworks at Shelter Cove. You’ll have a front row seat to see the magic aboard! This three hour cruise is only...

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