Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Bright condo with a private patio, walk ...

Summary:Queens Grant 601The Space:Ideal for a family vacation to Hilton Head Island, Queens Grant 601 is located near the entrance to Palmetto Dunes. This colorful, open, and airy hideaway features a great room with vaulted ceilings, comfortable...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
35 Crabline, Pool, Seasonal Beach Shuttl...

35 Crabline Court is a 4-bedroom, 4.5-bath modern coastal home that offers a private pool and an upsized front balcony overlooking the esteemed community of The Village at Singleton Beach. This property is located next to Chaplin Park which offers...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Ocean view condo with 2 balconies, new p...

Summary:Villamare 3430The Space:Villamare 3430 is a attractively refreshed condo, scenically located on the fourth floor of Villamare in Palmetto Dunes. Here in Building 3 of this oceanfront complex, you'll have vistas out over the treetops and a...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Beachfront getaway with WiFi, pools, hot...

Summary:Island Club 5101The Space:Heed the call of the beach at this ground-floor, oceanfront condo in the peaceful, 27-acre Island Club of Hilton Head! Outside, your furnished patio is ideal for morning coffee – courtesy of the Keurig and...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Wonderful sun-filled retreat w generous ...

Summary:Harbour Master 201The Space:This lavish Hilton Head condo, close to beaches and nightlife, is ideal for any couple’s hideaway or your next family vacation at the shore. Featuring sun-soaked interiors and plenty of coastal appeal, you’ll...

  • Hilton Head
  • 3 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Sea Pines - Newly Renovated - Greenwood ...

Summary:Dewberry Lane 17The Space:Sea Pines - Freshly Renovated - Greenwood Forest - 3 bedroom home on Dewberry Lane-Community pool, tennis/pickleball court, basketball court, and playground-Lots of games, books, and beach towels-Less than a mile...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8

Hilton Head Tours & Activities

Table Reservations

Victoria Valley Vineyards at Table Rock

duration: 1.5 hour cancellation_summary: 24 hour notice group_size: 20 accessibility: Fully accessible description: Reservation for a table during service hours

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...

Three Day Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$159.00

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...

DI 4 Hour Ultimate Lowcountry Day

meeting_point: Daufuskie Island, SC description: *Customized adventures are the best way to see and do the Lowcountry!* Description Designed for the family or small group interested in experiencing an authentic day in coastal Carolina. We...

Discovery Night at the Museum

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $75.00

duration: Varies cancellation_summary: We will happily refund your payment (minus a $5 per person admin fee) if you cancel more at 72 hours prior to the event. No refunds within 72 hours. meeting_point: Coastal Discovery Museum description: ...

Nightly Rental.  Premium 4 Passenger Electric Golf Cart. Pick up and drop off at your rental address only

meeting_point: PICK UP AND DROP OFF AT RENTAL ADDRESS ONLY description: About 48 Volt Electric Golf Cart with 2026 Lithium Battery. Equipped with seat belts, extended top, LED headlights (high and low beam), turn signals, horn, and digital...

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...

10 Day Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$80.99 - $161.99

description: **We ONLY deliver to address between Port Royal and South end of Island. If your address is not within these limits, please call 843-686-9113 before ordering to check if delivery is available to your address.** **This item is available...

Marsh Critters

Coastal Discovery Museum Hilton Head

Book online
$10.00

description: *Learn about the creatures of the salt marsh ! Great for families with younger children.* ___________________________________ Rates - **$10 per person aged 3 and up, under 3 Free** ___________________________________ ...

Hidden Treasures Tour

Hidden Treasures Bluffton

Book online
$20.00 - $500.00

description: Come and discover the Hidden, but not Forgotten Treasures of Historic Bluffton. Duration 45 Minutes About We will discover long lost Hidden Treasures in and around Beautiful Old Town Bluffton. More info There is a 4 person...

Lunar Paddle at The Landing

Saluda Lake Landing

Book online
$8.00 - $60.00

duration: 2 hrs cancellation_summary: Cancellations made 48 hours or more before the event are eligible for a full refund. Cancellations made within 48 hours of the event are nonrefundable, but your ticket can be transferred to a future paddle...

Sunset Cruise

Reel Native Fishing Charters

Book online
$175.00

description: Enjoy the Sunset on the Water! 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

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