Hilton Head, SC Vacations

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Featured Vacation Rentals

Colorfully Decorated 5th Floor Ocean Vie...

Barrington Oceanfront Complex | Just steps from the Beach **WINDOW/DOOR AND RECOATING PROJECT scheduled for Barrington Arms Building tentatively scheduled for October 2026 until April 2027.*2 Bedrooms | 2 Bathrooms*Sleeps 8*1 King, 2 Queens, Queen...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
2-bedroom beachside condo with balcony, ...

Summary:Hilton Head Resort 2417The Space:NOTICE:Escape to the island at this 2BR/2BA top-floor condo, located at the Hilton Head Resort and boasting direct walking access to the beach. Perks include a sleek kitchen, intelligent TVs, and a covered...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
New to the Rental Market!

5201 Hampton Place is a handsomely decorated one bedroom and two bath villa. It is located on the 2nd floor with a impressive ocean view looking over lush greenery.Upon entering the villa, you will immediately notice the unique white onyx floors and...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2
Sunny condo with central AC, pool, tenni...

Summary:Xanadu B10The Space:Located in the heart of Hilton Head Island's Forest Beach area, this serene condo is ready to host you and your guests for the ideal beach vacation! Savor on-site access to a shining, outdoor pool, two tennis courts...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Luxurious 4 Bedroom with many Updates!

This gorgeous Hilton Head Island vacation rental offers a ideal blend of luxury and comfort for your next hideaway. The cavernous living room provides plenty of room to relax and relax, with comfortable seating and a welcoming ambiance for gathering...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
5th floor Villa with Newly Renovated Bat...

Come savor this wonderfully decorated one-bedroom Windsor Place condominium with ocean vistas!Throughout the condominium, you’ll notice numerous updates made in 2026 that make this beach modern vacation rental especially appealing, including both...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 2

Hilton Head Tours & Activities

Rosie

Slow Rides LLC

Book online
$300.00 - $5,000.00

description: Cruise around Hilton Head Island in Style! Location Moke rentals are specifically for secondary streets (35 mph or less). Zones marked with an (*) please call 843-895-2063 to confirm utility trailer delivery before booking. ...

Explore Honey Horn

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about Honey Horn's past and natural history!* ___________________________________ Duration 1 Hour and 30 Minutes ___________________________________ About Begin your Honey Horn experience with this guided tour around the...

Three Hour Fishing Charter

Lowcountry Cowboy Fishing Charters

Book online
$480.00

description: Duration 3 Hours ___________________________________ About Catch sharks, other species, might catch some nice fish and see dolphins. (We have 27 different species of sharks in the Hilton Head waters so you never know what kind you...

Shelling, Shark Tooth, & Dolphin Excursion
Book online
$45.00 - $525.00

description: ___________________________________ Rates are based on 6ppl **2 Hours** - $300.00 **3 Hours** - $400.00 **4 Hours** - $475.00 *Can take a maximum of 12 people. Each additional person is $35* ___________________________________ ...

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...

Nine Day Bike Rental

Wheelz of Hilton Head

Book online
$60.00 - $120.00

description: Nine Day Bike Rental Rates Duration 9 days Rental Bikes Single Speed Cruisers - Low Entry Unisex Cruiser The ultimate old school cruiser, our Boardwalk is designed with a comfortable upright riding position perfect...

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...

2 Week Rental

Island Life Rentals and Tours

Book online
$54.00 - $370.00

duration: 2 Weeks 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...

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...

DI - Daufuskie Island History & Artisans Excursion

duration: 2.5 Hours meeting_point: County Landing near D’Fuskies pricing: $85 per person description: Description This 2.5-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of...

Private Morning Sail and Dolphin watch on Knot The Office
Book online
$315.00 - $395.00

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 passengers accessibility: Limited Handicap accessibility, Please call us to ensure we...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

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