Hilton Head, SC Vacations

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Featured Vacation Rentals

Gorgeous fifth floor oceanfront unit

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, roomy floor plans, designer decorated...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Cozy 2 Bedroom King Beds/2 Bathroom Town...

HILTON HEAD ISLAND. With these accommodations you can savor complimentary on-site tennis. Select from broad 2 and 3-bedroom, single-story or townhouse floor plans. Located on the Fazio golf course in Palmetto Dunes, all villas have deck areas that...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Charming villa with pool, balcony, full ...

Summary:Surf Court Villas 5The Space:The famed white shores of Hilton Head Beach are just one block away from this coastal charmer. Walk directly to the beach via the walkway across the street and spend sun-soaked days calming on the shore. For...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
3rd floor Villa, pool, tennis pickleball...

Summary:HH Beach & Tennis 319BThe Space:Located directly on the impressive Folly Field Beach in Hilton Head, SC, this striking villa at the Hilton Head Island Beach and Tennis Resort offers the ideal beachfront hideaway. With a plethora of amenities...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Open condo with pool, tennis, wooded bal...

Summary:Ocean Breeze 23The Space:This two-bedroom condo provides you and your family or friends with comfortable Hilton Head accommodations and offers a shared pool, shared tennis, and simple beach access. Walk to close by bicycle units and discover...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
463 Captains Walk is a gorgeous villa wi...

HILTON HEAD. This handsome oceanfront villa offers gorgeous vistas and a serene ambiance for a really calming stay. Located on the second floor of Captains Walk in Palmetto Dunes Plantation, the villa features a entirely equipped kitchen with...

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

Hilton Head Tours & Activities

Lighthouse Admission

Harbour Town Lighthouse

Book online
$8.00

description: Climb Through Time & Explore The History of the Island! Duration All Day Admission Open everyday 10 a.m. to sundown. About Climb 114 steps as you travel through Hilton Head Island history. Explore the Island’s rich history...

Eight Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$70.99 - $141.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Five Day Electric Bike Rental
Book online
$250.00

duration: 5 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...

Twelve Day Electric Bike Rental

duration: 12 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...

Private Afternoon Sail and Dolphin watch on Knot The Office
Book online
$325.00 - $425.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 people accessibility: Limited Handicap accessibility, Please call us to ensure we can...

PB Electric Bike Rentals

meeting_point: Palmetto Bluff

Private Lesson with Clark Sinclair

Palmetto Dunes Golf Academy

Book online
$130.00 - $650.00

meeting_point: George Fazio Course description: About Clark Sinclair, Director of Golf Clark Sinclair has been a member of the Palmetto Dunes staff since 1983 and has been teaching since 1986. He is a graduate of Presbyterian College. Clark...

Surfboard Rental

Forest Beach Surf & Cycle

Book online
$25.00 - $125.00

description: Rent with us! Duration 1 day, 3 day, or 1 week About Forest beach surf & cycle is your source for Hilton Head Island surf rentals!

Private Sunset Cruise (Up to 34 Passengers)
Book online
$998.00 - $1,497.00

duration: 2 or 3 Hours 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 group_size: Up to 34 Passengers description: Enjoy the Sunset...

PB Private Outback Excursion - 12 passenger

description: The Perfect Combination of Adventure and Fun! ___ Description This trip combines two of our most popular trips, The Dolphin Eco Tour and The Guided Kayak Tour, in an over the top remote location. A favorite of locals and visitors...

Pilates on the Water x HHI Pilates Club

duration: 1 Hour meeting_point: Broad Creek Marina description: An exclusive one-day event hosted by HHI Pilates Club, led by @trainwithlexi. Enjoy a 60-minute pilates session on the water aboard Bonjour. what_is_included: Mats will be provided.

Lowcountry Reptiles

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *The Locals You Haven't Met, Get to Know Your Reptile Neighbors!* ___________________________________ Duration 1 Hour ___________________________________ About This indoor program introduces you to some Lowcountry locals you...

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