Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Dog-friendly home with shared pool, tenn...

Summary:SpartinaThe Space:This private, dog-friendly home is ideal for families looking for a peaceful vacation hideaway. Skylights allow you to bask in the sun's natural glow. Slide a huge patio door to savor the view from an enclosed porch. Get a...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
Newly renovated beachfront condo with po...

Summary:HH Beach & Tennis 415ARThe Space:**Need to Know Notes**Admiral's Row Sprinkler ProjectAnticipated Start date: 1/15/2026Potential Construction Traffic and NoiseThere will be additional dumpsters and debris on property at this time.Timeline...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Welcoming Condo with Lagoon Views, Deck,...

Summary:Beachwalk 142The Space:Beachwalk 142 is a amazing choice for active travelers, offering painless access to basketball, tennis, and golf right within the community. Guests can also savor a roomy on-site swimming pool, and the beach as well as...

  • Hilton Head
  • 1 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
16 Singleton Shores, OceanViews, Pool, E...

16 Singleton Shores Manor, Hilton Head Island. Savor marsh and ocean vistas from every level of this home. Step into the open and bright living area, complete with a wet bar, pool table, and access to your private pool deck. Upstairs, an refreshed...

  • Hilton Head
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
4 BR Home, Private Pool, and Spa on Tran...

Appreciate striking lagoon vistas from your own private pool and spa or walk to the ocean in less than ten mins.. Located among live oak trees draped with Spanish moss, and overlooking a lush landscape, this private getaway is the ideal place for...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Ideal Island Villa with Shared Pool, Bea...

Summary:Beachwood Place 1HThe Space:When it comes to Hilton Head Island, there are few places as ideally located as Beachwood Place 1H. Boasting uninterrupted pool and ocean vistas, a private furnished balcony, and beach access mere steps away, you...

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

Hilton Head Tours & Activities

Lighthouse Admission

Harbour Town Lighthouse

Book online
$8.00

description: Climb Through Time & Explore The History of the Island! Duration All Day Admission Open everyday 10 a.m. to sundown. About Climb 114 steps as you travel through Hilton Head Island history. Explore the Island’s rich history...

11 Day Rental

Island Life Rentals and Tours

Book online
$45.00 - $315.00

duration: 11 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...

Pony Rides - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 3 group_size: Groups over 4 kids require a second pony description: Let your little ones experience the joy of horseback riding with our...

2 Day Rental

Island Life Rentals and Tours

Book online
$18.00 - $100.00

duration: 2 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...

Lessons

Daufuskie Marsh Tacky Society

Book online
$45.00 - $75.00

meeting_point: 281 Old Haig Point Rd description: Duration 1 hour About We offer a handful of lesson options to meet the needs of a wide variety of individuals looking to grow their skills around horses on the ground and in the saddle...

Hilton Head Yacht Fireworks - BYOB and FOOD
Book online
$4,100.00 - $7,200.00

duration: 4 Hours meeting_point: 1 Shelter Cove Ln, Hilton Head Island, SC 29928 group_size: Maximum 12 people description: ???? Tuesday Night Fireworks Are Back at Shelter Cove! Salt Shaker Charter at Night — Cruise Under the Stars in...

Palmetto Dunes Lagoon Charter

Palmetto Lagoon Charters

Book online
$410.00 - $625.00

description: Try some of the best fishing on Hilton Head Island - all while in the flat, calm waters of the Palmetto Dunes Resort lagoon system. A nursery to a variety of saltwater fish species, this lagoon system holds giant redfish, trout...

PB Intro to Stand Up Paddleboarding

description: *This introductory program will familiarize you with equipment, safety and paddle strokes. You'll be cruising down the creek in no time!* _____________ *(includes all equipment and Instructor/Guide)* Meeting Location - This...

3/4 Day Flats Fishing (6 Hrs)

Green Heron Adventures

Book online
$650.00

meeting_point: Beaufort and Hilton Head/Bluffton, SC description: Duration 6 Hours About Flats fishing trips are perfect for anglers looking to sight fish with both fly rods and/or light tackle. Year round, the majority of these trips target...

Sunset and Fireworks Kayak Tour
Book online
$55.00 - $125.00

description: *Few experiences are more memorable than watching fireworks from the seat of a kayak.* --- > Rates >- **Adults Single Kayak:** $55 >- **Adult & Child Double Kayak:** $90 >- **Two Adult Double Kayak:** $110 --- ...

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...

SCM WAHHI Daufuskie Island History Tour

description: *Catch a glimpse into Lowcountry history!* --- Description This 4-hour Daufuskie Island trip provides a glimpse into a fascinating chapter of Lowcountry history on the undeveloped side of the island. Visit several one-of-a-kind...

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