Hilton Head, SC Vacations

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Featured Vacation Rentals

Oceanfront luxury new to Island Getaway ...

**WINDOW AND DOOR REPLACEMENT PROJECT TENTATIVELY SCHEDULED September - April 2026 AND IS SUBJECT TO CHANGE. SCAFFOLDING WILL BE UP DURING THIS TIME. Due to the nature and scope of the work there is a possibility that your accommodations may be...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Quaint One Bedroom Condominium Steps fro...

You'll savor this cozy one bedroom condominium located in Barrington Court within Palmetto Dunes Oceanfront Resort! Updates have freshly been made to include all new stainless steel appliances, living room furnishings and linens in the primary...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2
18 Sand Dollar, Oceanfront, Pool, Free G...
4.8
(32)

18 Sand Dollar, Hilton Head Island. Your search for the ideal vacation rental ends here! With 7 bedrooms, 7 bathrooms, and an open-concept floor plan, this property is sure to impress. The upsized chef's kitchen is ideal for cooking up delicious...

  • Hilton Head
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
Lagoon and Golf Course Views!

This villa is conveniently located a short distance from the beach, general store, complex pools and much more! This condo features an open living room area with a Intelligent HDTV, comfortable seating and complimentary access to WIFI.The...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 5
arriott Harbour Point 2025 PGA Tour RBC ...

Discover this striking 2-bedroom gem in Hilton Head. This resort offers a fantastic living experience with a king bed, a twin bed, and a comfortable couch bed in the living room. Appreciate the convenience of amenities like WiFi, AC, and a exercise...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
46 Folly Field, Quick Walk to Beach, Lar...

46 Folly Field is freshly refreshed home in the sought-after Folly Field area is a ideal blend of comfort and convenience for a Hilton Head vacation. With 4 bedrooms and 3 full bathrooms, it offers ample space for families or groups. The proximity...

  • Hilton Head
  • 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 12

Hilton Head Tours & Activities

Ultimate Adventure

Hilton Head Helicopter Tours

Book online
$189.00

description: The Ultimate Adventure is an aerial flight that travels the full stretch of Hilton Head Island and the eastern shores of Daufuskie Island, offering expansive coastal views and memorable family moments. Passengers will fly over iconic...

Open Mic Registration

Mayfair Art Studios

duration: 2 Hours meeting_point: 1885 Hayne Street, Spartanburg, SC accessibility: Wheelchair Accessible pricing: $Free.99 description: Musicians from all genre backgrounds and walks of life are encouraged to sign up for our Open Mic. Our mission...

2 Hour Hilton Head Guided Boat Tour

Bluewater Adventure - Hilton Head

Book online
$115.00 - $149.00

description: Rates - Adults - $135 - Children - $115 - Fireworks Tour every Tuesday night - $135 ___________________________________ Duration 2 hours ___________________________________ Guided boat tours offered daily! Adventure awaits...

Sunset Jet Ski

Lowcountry Watersports

Book online
$159.00

duration: 1.5 Hours cancellation_summary: We allow cancellations up to 48 hours prior to scheduled activity. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 6 description: Experience the thrill of a...

One Week Electric Bike Rental

Hilton Head Outfitters - Bike Rental

Book online
$259.00

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...

Forts of Port Royal

Coastal Discovery Museum Hilton Head

Book online
$7.00 - $15.00

description: *Learn about the battle of Port Royal!* ___________________________________ Duration 1.5 Hours ___________________________________ About Join a knowledgeable museum docent for an in-depth walking tour of the defenses...

Ricochet Private Charter Fishing
Book online
$440.00 - $540.00

duration: 2 or 3 hours meeting_point: Palmetto Bay Marina, Hilton Head Island pricing: * $440 for a two hour charter * $540 for a three hour charter description: Board a Coast Guard inspected 25-foot boat "Ricochet" at Palmetto Bay Marina for a...

Day with The Native

Native Son Adventures 2

Book online
$350.00 - $1,180.00

duration: 2-8 hours cancellation_summary: Please let us know 48 hours in advance if anything causes you not to be able to go on your booked adventure. We will charge full price for not showing up for reservation without a 48 hour advanced notice...

Carolina HydroFly Parties

Carolina Hydrofly

Book online
$800.00 - $1,600.00

description: Private Party About Enjoy a 4 or 8 Hour Group Lesson. Can have up to 8 people (Half day) & 16 people (Full day) in your party. - Includes 10 minutes of instruction time, fuel, life jacket, and helmet **What's Included** ...

Private Day Sail

BC2 - Island Head

Book online
$900.00 - $2,500.00

duration: 2-6 Hours meeting_point: Broad Creek Marina, 18 Simmons Road group_size: Up to 6 People description: Sailing what_is_included: Sailing

Art Market: Fine Art and Craft Festival Tickets

Coastal Discovery Museum Hilton Head

Book online
$5.00

meeting_point: Coastal Discovery Museum at Honey Horn description: $5 per adult, FREE for ages 12 and under Original art for sale Food and drink available for purchase Advance tickets are not required, but only cash will be accepted for...

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