Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Ocean View , Top Floor, 6502 with roof, ...

Feel the tranquility of oceanside living in this meticulously appointed two-bedroom villa, boasting an awe-inspiring ocean panorama. Whether from the master bedroom, cavernous living area with new furnishings, or the broad top-floor balcony complete...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Oceanfront, 3rd-floor condo with corner ...

Sea Cloisters 311Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Immerse yourself in the soft blues of the ocean both inside and out at this oceanfront condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Large Three Bedroom Villa Directly on Ge...

This handsomely maintained three bedroom villa offers the ideal getaway for families looking for comfort and convenience. Located on the spectacular George Fazio Golf Course, there’s plenty of space for everybody to relax and relax.Step inside to...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Fully Updated Kitchen and Bathrooms with...

As you enter this villa you are greeted by the open concept Kitchen, Dining and Living Areas. The Kitchen has been refreshed with tiled countertops, stainless steel appliances and bespoke cabinetry. The Dining Area has seating for six. The Living...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
Oceanfront villa with WiFi, full kitchen...

Island Club 1203Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This splendid Island Club villa features modren renovations for ultimate comfort, plus access...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Luxurious oceanfront villa with panorami...

HILTON HEAD. This extravagant oceanfront complex offers the ultimate in resort vacation accommodations. You have a wide selection of 2 or 3 bedroom villas with vistas ranging from landscape to oceanfront, cavernous floor plans, designer decorated...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Gift Cards

Shelter Cove Marina Boat Rentals

Three Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$480.00

Duration 3 Hours ___________________________________ About Catch sharks, other species, might catch some nice fish and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you will catch....

Sail Sumo

H2O Sports

Book online
$325.00 - $425.00

duration: 1.5-2 hours 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: 1-6 people description...

Seven Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$55.00 - $131.00

Enjoy miles and miles of scenic bike paths Duration 7 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 available ...

Boomerang 2 Private Charter Fishing
Book online
$540.00 - $630.00

Rate **Three Hour** - $540 **Four Hour** - $630 About The Boomerang 2 is a comfortable 28 foot Parker center console that is powered by two brand new Suzuki outboards. We specialize in fun, family fishing excursions where you don’t need...

Two Hour Ocean Kayakor Stand Up Paddleboard Rental

Hilton Head Outfitters - Bike Rental

Book online
$40.99 - $56.99

Single Kayak 2 Hour Rental: $40.99 ________________________________ Double Kayaks or SUP 2 Hour Rental: $56.99

Marriott Vacation Club Daufuskie Tour

Tucked between Hilton Head and Savannah, and only accessible by boat, Daufuskie is a must-see in the Lowcountry!

Inshore Fishing

May River Excursions

Book online
$375.00 - $775.00

*Private trip along the backwaters of Hilton Head Island, Daufuskie Island, and Bluffton* ___________________________________ Rates are per private charter **2 Hours** - $375*-Only Recommended for Small Children* **3 Hours** - $475 **4 Hours*...

Paint the Pony - Montage Guests
Book online
$168.00

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Unleash your creativity with our Paint the Pony activity! This hands-on...

Luxury Pontoon Rental

Shelter Cove Marina Boat Rentals

Book online
$315.00 - $1,000.00

Duration 2 to 8 Hours About Rent a Luxury Pontoon, our most popular rental with all the advanced features you could want in a boat! Pontoon Boat Rental includes: ● 150 horsepower Yamaha engine ● Easy-to-operate vessel ● Roomy, comfortable...

Gift Cards

Carolina Hydrofly

Purchase the perfect gift: a gift card with a value of your choosing!

Bee City Zoo's Festival of Lights and Winter Wonderland Wagon Ride ENTRY STARTS AT 5PM Festival starts 6pm MAKE SURE TO ARRIVE AN HOUR PRIOR TO SELECTED WAGON TIME!!!

Choose your Wagon Ride time! Check out the Zoo before your reserved Winter Wonderland Wagon ride, entry begins at 5:00pm Festival kicks off at 6:00pm Come make magical memories with us and enjoy the zoo at night with lights! This ticket will...

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