Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Well Updated with Beach Contemporary Dec...

This refreshed, gorgeous two bedroom, two bath villa is located directly beside the Robert Trent Jones Driving Range and Clubhouse and is also just steps to the pool! You will feel instantly on vacation as you enter this coastal villa! The warm and...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Free Tennis & Pickleball, 3 minute Walk ...

NEW to Rental Market, NEW renovationsPROPERTY IS AVAILABLE FOR SHORTER STAYS. 3 NIGHT STAYS IN THE FALL and WINTER. Any arrival and departure date!!HILTON HEAD ISLAND. This is an oceanside villa complex that's just a short walk to the beach. The...

  • Hilton Head
  • 2 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
2 Beach Villa Steps From the Sand!

This three bedroom Palmetto Dunes Beach Villa is located directly on the sand and will surely meet all of your expectations for the ideal island vacation. The living room was freshly refreshed with high-end designer furnishings and accents and was...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Waterfront condo with seasonal pools, ho...

Island Club 141Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set your clocks to island time at this waterfront condo in the peaceful, 27-acre Island Club of...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Adorable ocean side villa with large win...

Sealoft 2032Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get ready for adventure in this alluring little oceanside villa in what will be your next favorite...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Dog-friendly house with private pool & l...

BoardwalkOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sit back and bask in the sun and nature of your own getaway with this three-bedroom property...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Sunrise Cruise

Flip Flop Charters

Book online
$895.00

Limited Availability! Duration 2 hours About There are few things as beautiful as a Hilton Head sunrise. Every morning we’re greeted with the most brilliant colors as the sun makes its way over the horizon. Join us for a cruise to...

Guided Kayak Tour

H2O Sports

Book online
$45.00 - $90.00

duration: 2 hour tour 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: Up to 14...

Private Lesson

Palmetto Dunes Golf Academy

Book online
$90.00 - $140.00

Duration & Rates - 50 minutes - 50-Minute Lesson with Doug Weaver - Director of Instruction: **$140** - Lesson with Head Professional: **$130** - Lesson with Assistant Professional: **$120** - Lesson with PGA Associate: **$90** About The...

Hilton Head Seafood Festival: Lowcountry Boil Dinner Cruise

duration: 2 Hours meeting_point: 1 Shelter Cove Lane, Hilton Head pricing: Adults: $145 Children 10yr-2yr: $99 Under 2: $20 description: Lowcountry Boil Dinner Cruise aboard The Ohana Step aboard The Ohana, Outside Hilton Head’s stunning luxury...

Advanced Wedge Play

Palmetto Dunes Golf Academy

Book online
$50.00

Make short approach shots the strongest part of your game! Duration & rates - 2 hours - $50 per student About When: Seasonal, by appointment only & course availability Where: TBD *Reservations are required*

Dolphin Cruise

Reel Native Fishing Charters

Book online
$65.00

description: See Dolphins Up Close! Duration 2 hours About We're committed to providing a stress-free experience to both new and returning clients. More info Minors must be accompanied by adults

Sunset Sail

Cheers Sailing Charters

Book online
$600.00 - $1,500.00

Stunning Sunset Views About 2.5 hour private sailing up the Broad Creek and into the Calibouge Sound. Sailing past Harbour Town and Daufuskie Island on a 45 ft Morgan Nelson Merrick Racing sailboat. Stunning sunset views over the water and...

Kids Summer Splatter-Paint Camps

Color Me Greenville

Book online
$225.00

duration: 30 mins meeting_point: 50 Liberty Ln., Greenville, SC 29607 description: Kids Summer Splatter-Paint Camps

Private Lesson with Michael Decker

Palmetto Dunes Golf Academy

Book online
$90.00 - $450.00

About the Palmetto Dunes Golf Academy The Palmetto Dunes Golf Academy in Hilton Head, South Carolina, is one of the most respected golf schools in the world. Featuring lessons, clinics and one-on-one golf instruction from former PGA Tour...

Sunset Sport Crabbing Adventure

Join us for a Sport Crabbing Adventure with a sunset! Duration 2 hours About Our summer night Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on vacation! You will...

Six Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

description: Enjoy miles and miles of scenic bike paths Duration 6 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...

Two Week Electric Bike Rental
Book online
$475.00

duration: 14 Days meeting_point: 112 Arrow Rd Hilton Head Island, SC 29928 US description: Magnum Low Rider 2.0. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2 - 6'6. The Low Step-Thru makes it easier to get on...

Find your perfect Hilton Head

Fishing Charter

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