Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

1665 St. Andrews Commons Great Family La...

Absolutely inviting one bedroom Hilton Head villa with a loft and a sleeper couch. You will feel instantly on vacation the min. you walk through the doors! Coastal colors and beach vibes throughout this fabulous villa. The entirely equipped kitchen...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Beachside Townhome | Parking. Pool + Ful...

The Village at Palmetto Dunes offers a casual Hilton Head stay just steps from the beach, with simple access to golf, tennis, pickleball, and spectacular bicycle paths. Located within Palmetto Dunes Resort, this property places you close to Shelter...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Freshly Updated Throughout!

Savor the best of Palmetto Dunes Oceanfront Resort on Hilton Head Island from this cavernous 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...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Pet friendly centrally located villa in ...

Feel the best of Hilton Head Island from this delightfully located 2-bedroom, 2-bath villa in the heart of Harbour Town within the world-acclaimed Sea Pines Resort.Leave the car behind and savor one of the most walkable locations on the island. Just...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Bright, comfortable villa near beach wit...

Summary:Links 12BThe Space:The Links 12B is a light, bright, and cavernous three-bedroom, three-bathroom villa located on Barony Golf Course in Port Royal. Recently refreshed with wood tile floor throughout the living area and primary bedroom, plus...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Amazing & newly updated Palmetto Dunes R...

Stunning 4-Bedroom Lagoon-Front Retreat in Palmetto Dunes — Steps from the BeachAppreciate one of the most spectacular vistas in all of Palmetto Dunes from this freshly refreshed 4-bedroom, 3-bath vacation home. Overlooking long, serene lagoon...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 13

Hilton Head Tours & Activities

Jet Ski Rental

Wateree Marina

Book online
$125.00 - $700.00

meeting_point: Wateree Marina description: Half or Full Day Jet Ski Rentals Know Before You Go - All jet skis may accommodate two passengers total. - All renter's/driver's must be 21 years or older. - All passengers must be 16 years or older. ...

Two Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$40.00 - $100.00

description: Enjoy miles and miles of scenic bike paths Duration 2 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

Hilton Head Outfitters - Bike Rental

Book online
$445.00

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...

Gift Cards

Shelter Cove Marina Boat Rentals

Baby Gear Rental Package • One Day

Lowsea Bike, Beach and Baby Rental

Book online
$190.00 - $235.00

duration: 1 Day cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Private Guided Dolphin Kayak Tour - Just you and your family!

description: Private Dolphin Kayak Tour Duration 2 hours About Explore the beautiful salt marshes of Hilton Head Island with your group only! Private Tours are for smaller groups of 2 to 12 people that want a private guide to be with your...

Dolphin Tour

Island Head - Broad Creek

Book online
$10.00 - $499.00

duration: 90 Minutes cancellation_summary: Customers will receive a full refund or credit with 72 hours notice of cancellation. meeting_point: Broad Creek Marina 18 Simmons Road Hilton Head Island, SC description: See Dolphins up Close! Join us...

PB Family Ski Day
Book online
$245.00 - $1,290.00

description: *Certified instructors will show you the ropes on this 2 1/2 hour program! Ski, tube, wakeboard and kneeboard.* _________ About Cruise from Palmetto Bluff back to our favorite ski grounds and learn how to water-ski, wakeboard...

Cocktails & Camellias

Coastal Discovery Museum Hilton Head

Book online
$200.00

duration: 3 hours meeting_point: 70 Honey Horn Dr, Hilton Head Island, SC min_age: 21 accessibility: Wheelchair accessible description: Immerse yourself in the beauty of the Lowcountry at *Cocktails & Camellias*, an elegant evening set against the...

PVT Shark Tooth 12p

description: Discover Shark Tooth Island! ___ Description Enjoy a boat cruise from Hilton Head Island through the back waterways to Shark Tooth Island (near Savannah, Georgia) where you can hunt for shells, shark teeth and other ocean...

Lake Wateree Private Charters

Captain Jake's Guide Service

Book online
$350.00 - $850.00

duration: 3-8 hours meeting_point: Lake Wylie Boat Ramp-890 Nivens Landing Dr Fort Mill, SC 29708 description: Whether you're looking for an action-packed day of tubing and island hopping or a laid-back cruise to soak in the views, we’ve got you...

Bunch Bike - Family E-Bike Fun!

Pedego Electric Bikes Greenville

Book online
$109.00

duration: 6 to 8 Hours meeting_point: Pedego Electric Bikes Greenville. Located at Hampton Station - 1320 Hampton Ave Ext. STE 11A Greenville, SC 29601 description: Experience family fun like never before! ???? Experience the Thrill of...

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