Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Quiet Waterfront Condo with WiFi - Pools...

Island Club 2502Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Soak up the beautiful vistas of the Atlantic Ocean from the balcony of this comfortable Hilton...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 7
Dog-Friendly Villa with Pool, Tennis, Pa...

Evian 120Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This first-floor Evian property offers comfort along with a peaceful and calming ambiance that will...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
434 Captains Walk, Oceanfront,1st Floor ...

434 Captains Walk Hilton Head Island is an oceanfront 3-bedroom corner villa that has freshly undergone a complete bespoke remodel, featuring brand new cabinets, quartz countertops, appliances, floors, doors, ceilings, paint, and bathrooms with new...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Mid-Island Marvel at Hilton Head Resort ...

Hilton Head Resort 4129Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the sought-after Hilton Head Resort, this delightful condo is a leisurely...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
NEW Palmetto Dunes Condo - Queen's Grant...

We can't wait to host you at one of the newest properties managed by Vacation Ready Services! Located in the Queen's Grant subdivision within the highly sought after Palmetto Dunes Resort, this 3 bed & 2.5 bath condo is conveniently located with a...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Bright and spacious home in Sea Pines,  ...

17 Sand Fiddler RdOur 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 family hideaway in Hilton Head, SC! This immaculate and bright home...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10

Hilton Head Tours & Activities

Lessons

Daufuskie Marsh Tacky Society

Book online
$45.00 - $75.00

Duration 1 hour About We offer a handful of lesson options to meet the needs of a wide variety of individuals looking to grow their skills around horses on the ground and in the saddle. Appropriate for ages 7+ through adult, who are total...

Solaris - Happy Hour Cruise (up to 6 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: Up to 6 people description: Book a luxurious charter aboard Solaris today! **Our private charters accommodate up to 6 passengers, ensuring an intimate and personalized experience for...

Beach Discovery Walk

Hilton Head Island Recreation Association

Book online
$5.00 - $24.00

duration: 1.5hrs meeting_point: Fish Haul Beach Park group_size: Up to 25ppl description: Explore the amazing beach front eco-system from the tides to the shoreline and all the creatures that call this home!  You’ll be amazed by what we...

Inshore Charter

Out Of The Blue Fishing Charters

Book online
$420.00 - $900.00

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...

One Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$50.00 - $250.00

description: Electric Bike Rental Duration 7 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...

Private Sunset & Fireworks Cruise - 12p

meeting_point: Hilton Head, SC description: This 3+ hour private excursions departs from Shelter Cove Marina where your captain will give you a tour and educate you of the salt marsh ecosystem. Bring your camera and take in the sights of a...

Body Board Rental

Forest Beach Surf & Cycle

Book online
$40.00

description: Rent with us! Duration 1 week About Forest beach surf & cycle is your source for Hilton Head Island body board rentals!

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...

Nature Writing: Kayak on the Chechessee and Write about It

duration: 3 meeting_point: 310 Okatie Highway description: We who live in the South Carolina Lowcountry are fortunate to be surrounded by its extraordinary nature – the marsh and its seasons, live oaks dripping with Spanish moss, 180 degrees of...

Open Climb

Hilton Head Island Recreation Association

Book online
$5.00 - $20.00

duration: 1-3 Hours cancellation_summary: Cancellation Policy: To be eligible for a full refund, all cancellations must be made up to 24 hours before the scheduled start time. We can also move you to another session time if spots are...

Hilton Head -> Daufuskie Island Daily Round Trip Ferry
Book online
$10.00 - $99.00

duration: 45 Minute Ferry Time Each Way cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: 18 Simmons Road Hilton Head Island, SC description: Hilton Head -> Daufuskie Island...

Short Game Clinic

Palmetto Dunes Golf Academy

Book online
$50.00

Duration & Rates - 50 minutes - $50 per student About Learn the sand fundamentals. This is the easiest shot in golf when executed correctly. Learn why the pros would rather be in the sand trap than in the rough. 5:1 ratio. Reservations...

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