Hilton Head, SC Vacations

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Featured Vacation Rentals

Beautiful lagoon views, new living room ...

Welcome to your coastal getaway in the heart of Palmetto Dunes Oceanfront Resort on Hilton Head Island! This gorgeously appointed 4 bedroom, 4 bathroom townhome offers the ideal blend of indoor comfort and outdoor tranquility, appealingly located...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Oceanview Condo with WiFi, Hot Tub, Pool...

Summary:Island Club 6304The Space:If you want to swim in a exhilarating pool or hot tub, fish in a lagoon, or play five sets of tennis on a clay court, know that you can do all of these things and more when you stay at this Island Club condo! Rent a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
12 Whelk, Steps to the Beach, Private Po...

Welcome to 12 Whelk Street, Hilton Head Island's premier vacation destination, where beachside luxury meets unmatched convenience. Just 145 feet from the pristine sands of Bradley Beach, this freshly remodeled four-story property offers gorgeous...

  • Hilton Head
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Charming one bedroom villa in Hilton Hea...

This appealing ground-level, one-bedroom villa is sure to be your home away from home while visiting in Hilton Head! Coastal vibes flow throughout this inviting villa, and the convenient ground-level location makes coming and going a breeze.The...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
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
Snowbird Friendly villa with Golf View, ...

Summary:Racquet Club Villas 2361The Space:Welcome to Racquet Club Villas 2361, a second-floor, condo tucked away in the Harbour Town Area of Sea Pines. This cavernous vacation rental offers golf course vistas and recent updates, creating a bright...

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

Hilton Head Tours & Activities

Water Taxi: Daufuskie → Savannah

Low Country Drifters

Book online
$240.00

duration: 45 minutes – 1 hour meeting_point: Savannah, Georgia group_size: Accommodates up to 6 people description: Enjoy a scenic boat ride through the Low Country's stunning waterways, arriving at this secluded island known for its rich history...

Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $950.00

description: This trip is great for kids or anyone who wants a little taste of Lowcountry fishing! **If you don't see a time on the calendar that works for you, text us at 843-422-5438 to see if we can accommodate you!** Duration 2 to 6...

Juneteenth Children’s Drum Camp

Historic Mitchelville Freedom Park

duration: 2 hours min_age: 3 max_age: 15 description: Let the rhythm lead the way at this hands-on children’s drum camp. Participants will learn basic drumming techniques, explore rhythm and movement in a group setting, and take part in a parade...

Three Day Bike Rental

Wheelz of Hilton Head

Book online
$40.00 - $80.00

description: Three Day Bike Rental Rates Duration 3 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

Ladies Only Clinic

Palmetto Dunes Golf Academy

Book online
$50.00

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. With a student-instructor ratio of 5:1...

Hack, Snack and Roadie Ride

Daufuskie Marsh Tacky Society

Book online
$450.00

meeting_point: Varies description: Duration 3.5 Hours Please Note This is experience is designed for novice or better riders who are comfortable with longer hours in the saddle and are able to independently mount/dismount their horses easily...

Sunset Kayak Nature Tour
Book online
$50.00 - $130.00

duration: 2 hours meeting_point: Hilton Head Island, SC pricing: Single Kayak - starting at $50 Adult & Child Double Kayak - starting at $90 Two Adults Double Kayak - starting at $100 Adult & Two Children Double Kayak - starting at $130 description...

Pilates for Pink — A Breast Cancer Donation Class

duration: 1.5 Hours meeting_point: Broad Creek Marina group_size: Maximum 12 guests description: An exclusive one-day event hosted by HHI Pilates Club. Enjoy a 90-minute pilates session on the water aboard Bonjour. 100% of the proceeds will be...

Glow With the Flow Fridays

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Light up your weekend! Glide down the river with glowing gear, good vibes, and nonstop Friday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with friends, and soak in the magic of the...

Hilton Head Yacht Cruise

Salt Shaker Charter LLC

Book online
$3,750.00 - $6,600.00

duration: 4 - 8 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: Your Cruise, Completely Customized! At Salt Shaker Charter, every cruise is tailored to you. From intimate getaways to...

Private Dolphin Discovery Tour - One Hour

Island Life Rentals and Tours

Book online
$35.00 - $250.00

duration: 1 Hour group_size: 12 - 14 Max description: See dolphins up close! Now you can enjoy the thrill of a small boat expedition for nearly the same cost as the big boat "bus tour". Join Island Life for a great introductory cruise through the...

Four Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 4 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...

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