Hilton Head, SC Vacations

HiltonHead-SC.com logo

Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

Spacious Palmetto Dunes condo with priva...

St Andrews Common 1873Our 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 hideaway in Hilton Head, SC! This beautiful condo located in...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Spacious one-level vacation rental offer...

This roomy 2,041 sq. ft. one level vacation rental offers the best of both worlds! A short walk to the beach and superb vistas of the fairways on the Fazio Golf Course from your upsized deck. From the tiled entryway to the sizable living room with...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Hilton Head villa conveniently located j...

This delightfully decorated three-bedroom Hilton Head villa offers the ideal coastal getaway, just a short walk to the beach and only steps from the community pool.This refreshed villa features a entirely equipped kitchen, a 50-inch HDTV in the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 6
Sunny Ocean Club Condo | Pool & Private ...

Ocean Club 35Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located just steps from the waves in the beachfront Ocean Club complex, this 2BR/2BA two-story...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Harbourtown Gem

Summary:Cutter Court 923The Space:You will definitely appreciate your next vacation to Sea Pines when staying in the heart of world-famed Harbour Town in this handsome villa at 923 Cutter Court, this pristine roomy gem is a impressive third-floor...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Beach-view condo in oceanfront complex w...

Breakers 225Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'On-site beach access and a walkable location? Say less! This no-frills condo in Hilton Head Island...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4

Hilton Head Tours & Activities

Tubing and Dolphin - 6 max

meeting_point: Hilton Head Island, SC description: Family Fun With Nature, Tubing and Exploring! --- Join us for a boating and tubing tour through the Lowcountry waters! Watch for birds and dolphin through the salt marsh ecosystem and get behind...

PB Private Outback Excursion - 6 passenger

meeting_point: Palmetto Bluff, Bluffton 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...

PB Full Moon Kayak Nature Tour
Book online
$115.00 - $230.00

description: *Explore the Lowcountry waters by the light of the moon!* __________ About A beautiful and serene nature tour, in the moonlight, along the pristine May River. No kayak experience is necessary. _________ Duration 2 hours

Five Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$64.99 - $129.99

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...

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...

Coligny Food Tour

Food Tours Hilton Head

Book online
$64.95

description: Explore Coligny and its culinary offerings! Duration 2 hours and 30 minutes What's Included: - All tastings (amounts to a whole meal) - A fun and informative tour of the Coligny area About We will meet at our first location...

12 Day Rental

Island Life Rentals and Tours

Book online
$48.00 - $335.00

duration: 12 Days description: Delivery Procedures Upon delivery our driver will send an email or text message confirming your delivery is complete. In that communication they will include your lock combination. Please keep your bicycles locked at...

Glow With the Flow Fridays

Vintage View River Retreat

Book online
$20.00 - $45.00

duration: 3 Hours description: Light up your weekend! Glide down the river with glowing gear, good vibes, and nonstop Friday night fun. This 3 hour adventure lets you float while the sun goes down, laugh with friends, and soak in the magic of the...

Day with a Native - The Island Girl

Native Son Adventures

Book online
$365.00 - $1,260.00

duration: 3 to 8 hours description: Choose from a range of half‑day to full‑day coastal excursions tailored to your interests—fish, hunt for shark teeth and fossils, crab like a local, paddle with dolphins in uncrowded areas, birdwatch, or...

Horse Whispering (Montage Guests)

duration: 45min group_size: 4 description: Most people are taught to make horses respond to them. In this experience, you'll learn something fundamentally different: how to speak the horse's own language. Led by Longfield's Equestrian Director, a...

Hilton Head Full Moon Cruise

Island Head - Broad Creek

Book online
$59.99

description: Get on the water under a low country full moon! Duration 90 minutes About This is a one of a kind experience to see a full moon from the water. Enjoy a 90 minute slow cruise as you take in the beauty of the low country in a...

Inshore Fishing Charter

Gone Fishing HHI

Book online
$500.00 - $600.00

description: Fish like a local! Duration 3 Hours About Targeting Red Drum, Black Drum, Seatrout, Flounder, and Sheepshead in local tidal creeks and nearby waterways with light tackle. This trip is great for all experience levels! More...

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