Hilton Head, SC Vacations

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Featured Vacation Rentals

New to the rental market, 4th row home!

This lagoon front Hilton Head Island home is located directly across the street from the beach access point and sits on one of the biggest tons in Palmetto Dunes Oceanfront Resort. The back deck is the ideal spot to appreciate the coastal breeze and...

  • Hilton Head
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Updated oceanfront villa with amazing vi...

Ocean One 215Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Start your day with elegant sunrises over the Atlantic Ocean from the comfort of Ocean One 215...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Sunset Rentals | Beach Villa 3
3.9
(11)

Years from now you'll still be talking about the view from this Palmetto Dunes Resort beachfront villa on Hilton Head Island. Just steps from the sand, this 3 level, 3 bedroom and 4-bath Palmetto Dunes villa will surely meet all of your expectations...

  • Hilton Head
  • 3 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Brand new coastal renovated beach villa ...

Brand new coastal modernized beach villa just steps from beach and pool. With quartz counters, new white shaker cabinets, designer tile walk-in shower, striking ocean vistas. Everything has been refreshed! Ideal for a family up to 6 people.Pack...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
2516 Windsor Place II- Renovated for 202...

Welcome to this 5th floor Windsor condominium! The Kitchen has quartz countertops and is completely-equipped with everything you'll need to prepare for your family. There is Kitchen bar seating for two as well. The Kitchen looks out to the Dining...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Homey Condo with Lagoon View from Balcon...

Island Club 122Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'When you book this comfortable Island Club condo, you’ll be able to prepare healthy meals by...

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

Hilton Head Tours & Activities

Dolphin Cruise

Reel Native Fishing Charters

Book online
$65.00

See Dolphins Up Close! Duration 2 hours About We're committed to providing a stress-free experience to both new and returning clients. More info Minors must be accompanied by adults

After School Skate Club

Hilton Head Island Recreation Association

Book online
$100.00 - $600.00

duration: 4 Weeks • 1 Day Per Week • 2 Hours Each Day meeting_point: Island Recreation Center min_age: 7 max_age: 18 group_size: Up to 20 Campers description: Learn from one of the best and most experienced instructors on Hilton Head at the...

Ladies Only Clinic

Palmetto Dunes Golf Academy

Book online
$50.00

Learn something new every day! Duration 50 minutes About The Academy presents a daily golf clinic at the Arthur Hills Golf Course, featuring special instruction on the stroke of the day. With a student-instructor ratio of 5:1, you can be sure...

One Week Beach Cart Rental

Hilton Head Outfitters - Bike Rental

Book online
$32.99

WIDE ALL-TERRAIN BACK WHEELS provides easy roll over sand HOLDS ALL YOUR BEACH GEARS, carries cooler, beach towels, umbrellas and more! EASY OPEN AND CLOSING, opens in seconds and folds flat for travel and storage MULTI PURPOSE - can be used for...

Three Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$150.00 - $675.00

Electric Bike Rental Duration 21 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all without...

Solaris - Sandbar Sunbathing Charter (7 to 10 passengers)

duration: 3.5 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious charter aboard Solaris to the Sandbar only accessable by boat! Escape to paradise with our exclusive 3.5-hour charter aboard...

Alligator & Wildlife Tours
Book online
$22.00 - $350.00

duration: 1 hour cancellation_summary: All reservations are subject to our 24 hour cancellation policy meeting_point: Fish Island Sea Pines Forest Preserve group_size: Up to 12 passengers description: Join us on a 1-hour guided tour of the...

Baby Gear Rental • Five Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $150.00

Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 5 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and happy ...

Powerboat Dolphin and Monkey Adventure

Otter Sailing Adventures LLC

Book online
$300.00

duration: 2 hours meeting_point: Saint Helena Island SC (exact location will be emailed) description: Hop on our 17’ Boston Whaler powerboat for an amazing low country adventure where we explore the creeks and rivers of the Saint Helena Sound...

Three Hour Vanishing Island and Dolphin Nature Watch Tour
Book online
$375.00 - $395.00

*Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

Ten Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$78.60 - $187.10

Enjoy miles and miles of scenic bike paths Duration 10 Days About Free locks with all rentals. Baskets and helmets also available - please select during check-out! More info Free locks with all rentals - please select during...

Classic Splatter Party - Deluxe

Color Me Greenville

Book online
$40.00 - $600.00

duration: 1.5 Hours meeting_point: 50 Liberty Ln., Greenville, SC 29607 min_age: 5 group_size: 15 Max description: Imagine a splatter paint party, a wild, colorful experience where you become artists by flinging, dripping, and splashing paint...

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