Hilton Head, SC Vacations

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Featured Vacation Rentals

Newly-renovated ocean front condo on the...

Shorewood 511Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Shorewood 511, an spectacular oceanfront condo that has been completely remodeled...

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

HILTON HEAD ISLAND. With these accommodations you can appreciate 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...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Coastal-Chic Poolside Home w/ Large Balc...

Fiddlers Cove 27EOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Totally updated in December 2021, this top-floor two-bedroom/two-bath condo offers the...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
9 Sandy Beach, Close to Beach, Pool, Ele...

***NOW OFFERING COMPLIMENTARY SPA HEAT FOR MARCH - MAY 22*** UPON BOOKING, GUEST MUST LEAVE IN COMMENTS THAT THEY WANT SPA HEAT OR CALL OUR RESERVATIONS TEAM TO CONFIRM. THIS IS FOR NEW BOOKINGS MADE ON OR AFTER 1/30/26***9 Sandy Beach Trail, Hilton...

  • Hilton Head
  • 6 Bedrooms
  • 8 Bathrooms
  • Sleeps 21
Coastal condo with indoor and outdoor po...

Spa On Port Royal Sound 1314Our 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 beach hideaway in Hilton Head, SC! This beautiful condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Second row high-end luxury home is mere ...

Located in the charming South Forest Beach area, this freshly constructed (2025) second row high-end luxury home is mere steps from the beach and conveniently located between Coligny Plaza and Sea Pines. The home features six (6) bedrooms, two of...

  • Hilton Head
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 23

Hilton Head Tours & Activities

Solaris - Morning Sightseeing Cruise (7 to 10 passengers)

duration: 2 Hours meeting_point: Hilton Head Island group_size: For 7 to 10 passengers description: Book a luxurious morning charter aboard Harbour Town's Solaris now! **Our private charters accommodate seven to ten passengers, ensuring an...

13 Day Rental (Walk Up)

South Beach Bike Rentals

Book online
$102.18 - $243.23

description: Enjoy miles and miles of scenic bike paths Duration 13 Days About Make your reservation online. Come pick up your bike at the time of your choosing. More info Free locks with all rentals. Baskets and helmets also...

Parasailing

Island Head- Hilton Head Harbor

Book online
$49.00 - $999.00

meeting_point: Hilton Head Harbor description: *High Flying Family-Fun Parasail over Hilton Head.* ___________________________________ Rates **Flyer (Ages 6+):** $95 **Observer (All Ages):** $49 ___________________________________ ...

One Week - 4 Passenger Quad Stroller Wagon with Removable Canopy

description: PERFECT CARRIER FOR KIDS – Baby bags. Booster seats. Strollers. Sometimes, taking our little ones on the go with us is nearly impossible! Babies and toddlers alike love strolling around in the WONDERFOLD X4 Wagon, secured in a 5-point...

One Day Single Jogging Stroller

Hilton Head Outfitters - Bike Rental

Book online
$25.99

description: These Schwinn brand strollers are made of lightweight aluminum and are great at the beach at low tide or on our miles of bikes paths.

Baby Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $150.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 4 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

Four Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$189.00

meeting_point: 80 QUEENS FOLLY RD HILTON HEAD, SC 29928 description: Our e-bikes are a fun and easy way to get explore heavenly Hilton Head, South Carolina, providing a battery-powered "assist" that comes from pedaling. When you push its pedals, a...

Private Beach Sail On Hobie Catamarans

Hilton Head Island Recreation Association

Book online
$275.00

duration: 1.5 hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 group_size: Up to 4 people description: 1.5 hour, up to 4 participants. Take a ride on our 17’ Hobie Getaway with one of our US Sailing...

Public Sailboat Charter

Charleston Sailboat Charters

Book online
$125.00 - $1,599.00

Duration 2.5 Hours About After a brief safety speech, we will shove off the dock and head into the scenic Charleston Harbor. As we raise the sails and turn the engine off, you'll immediately feel the relaxation set in and discover why the...

Lowcountry Ruins Setting

Island Life HH Photography

Book online
$195.00 - $745.00

duration: Up to 60 minutes cancellation_summary: Full refund if unable to reschedule due to weather; otherwise subject to rescheduling. meeting_point: Stoney Baynard Ruins in Sea Pines description: Are you looking for the perfect Hilton Head family...

Summer Fireworks and Kayaking Dolphin Nature Tour

description: Kayaking Tour and Shelter Cove Fireworks Display! Duration 2.5 Hours *Please arrive 30 minutes prior to your scheduled tour time* On Tuesday evenings in the summer months our regular 2 hour evening sunset tour is followed by the...

Pilates for Pink — A Breast Cancer Donation Class

duration: 1.5 Hours meeting_point: Broad Creek Marina group_size: Maximum 12 guests description: An exclusive one-day event hosted by HHI Pilates Club. Enjoy a 90-minute pilates session on the water aboard Bonjour. 100% of the proceeds will be...

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