Hilton Head, SC Vacations

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Featured Vacation Rentals

First Floor Condo near the sound with be...

Spa On Port Royal Sound 3134Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head, this striking condo is the ideal beach...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
2 Beach Villa Steps From the Sand!

This three bedroom Palmetto Dunes Beach Villa is located directly on the sand and will surely meet all of your expectations for the ideal island vacation. The living room was newly refreshed with high-end designer furnishings and accents and was...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Spacious Villa with Shared Pool, Hot tub...

Island Club 113Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Visit this cavernous Island Club villa to appreciate an adult calming pool and hot tub, shared...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Ocean-View Condo | Tennis, 3 Pools, Beac...

Hilton Head Resort 1403Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Boasting prime ocean and marsh vistas from the private top-floor balcony, a choice...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Third floor Penthouse with wonderful oce...

**METAL ROOF REPLACEMENT SCHEDULED BETWEEN SEPTEMBER 2025-APRIL 2026 AND IS SUBJECT TO CHANGE. SCAFFOLDING WILL BE UP AT TIMES THROUGHOUT THE PROJECT. Due to the nature and scope of the work there is a possibility that your accommodations may be...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Spacious Beach Getaway with a Private Po...
5.0
(11)

Striking second row 5 Bedroom home that has been completely refreshed and has a private pool. The floor plan is unique, and offers tremendous flexibility providing both privacy and great common areas that are ideal for two families. Private & gated...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Luxury Pontoon Rental

Shelter Cove Marina Boat Rentals

Book online
$315.00 - $1,000.00

meeting_point: Shelter Cove Marina description: 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...

PB Private Daufuskie Island Tour - 6 passenger

description: *Catch a glimpse into a fascinating chapter of Lowcountry history* --- Description Tucked between Hilton Head Island and Savannah, and accessible only by boat, Daufuskie Island is a real gem. This trip provides a glimpse into a...

Hibachi Dinner Cruise

Island Head - Broad Creek

Book online
$19.99 - $109.99

duration: 2 Hours 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: Hibachi Dinner Cruise Experience an...

Beach Gear Rental • Three Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $75.00

duration: 3 Days 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...

SCM PVT Dolphin Eco 12p

description: *Our Most Popular Boat Trip!* --- Description Explore the marsh and search for the infamous Atlantic Bottlenose Dolphin... Join us for a tour on Broad Creek watching for birds and dolphins in the salt marsh ecosystem. Explore...

13 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$95.99 - $191.99

description: 13 Day Rental Rates: - 16” Kids Beach Bike: $95.99 - 20” Kids Beach Bike $95.99 - 24” Youth Beach Bike: $95.99 - 26” Bike w/ Child Seat: $110.99 - 26” Mens Beach Bike: $95.99 - 26” Unisex Beach Bike: $95.99 - 12" Balance...

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...

Seven Day Golf Cart Rental

Wheelz of Hilton Head

Book online
$920.00 - $1,365.00

description: Golf Cart Rentals! Duration 7 days Please Note * Golf Cart Rentals CANNOT be delivered * Must be picked up at our location * Golf Carts need to stay within a 4 mile radius of our location. * Golf Carts cannot be booked online...

Flyboard 40 Minute

Carolina Hydrofly

Book online
$139.00

description: 40 Minute Flyboard Pro Series Experience About Each guest will have 30 minutes of flight time and 10 minutes of instruction time. If you would like to book for more than one person, then please process one booking per person by...

One Week Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$41.99

description: Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold small items. Folds with one pull of the strap inside the wagon. Includes storage cover.

Four Hour Private Inshore/Nearshore Charter

group_size: Up to 6 guests description: Experience inshore to nearshore fishing around Hilton Head Island aboard the 29ft World Cat "Sweet Pea." Fish for seasonal species such as cobia, bull reds, king mackerel, tarpon, and sharks while an...

Butterfly Learning Station

Coastal Discovery Museum Hilton Head

meeting_point: Coastal Discovery Museum description: About Experiencing the enchantment of a native butterfly garden and observing all four stages of the butterfly life cycle is a unique opportunity available to people of all ages at the Coastal...

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