Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Intimate, Yet Spacious Villa with Shared...

Summary:Evian 275The Space:Treat yourself to a calming beach vacation with this two-bedroom Evian townhouse villa, which features access to a shared pool, tennis courts, and a calming patio with a striking view of the property’s private...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
4 Bedroom Oceanfront Villa in Windsor Pl...

This impressive 4 bedroom oceanfront condo has everything that your family needs for an extraordinary hideaway. The kitchen has been gorgeously refreshed with high-end appliances and granite countertops. The Primary bedroom has a King bed and an...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 8
Updated Condo with Fast WiFi, Shared Poo...

Summary:Sea Side Villas II 149The Space:Get a taste of island bliss in this classy condo in the heart of all the action here on Hilton Head Island! Whether you have come to lounge by the shining shared pool, sip a coffee on the private balcony, play...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Oceanside 1st floor villa in Palmetto Du...

This is your happy place! Charming ocean side villa a short walk to the beach!HILTON HEAD ISLAND. Wendover Dunes is a pretty ocean-side villa complex that is just a short walk to the beach. Located next to the Barrington Enclave in Palmetto Dunes...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Double Master Suite Luxury 4 BR Sea Pine...

Wonderful luxury Sea Pines four bedroom home with private pool and spectacular vistas of the live oaks wrapping around the golf vistas. Handsome high ceilings with giant kitchen and tons of living space outdoors. Oversize kitchen and dining area...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 11
Gorgeous and sunny home with pool, beach...

Summary:Kingston Dunes 68The Space:Roomy, and private, the ideal Hilton Head Island hideaway exists, and it's here! This secluded home is against the backdrop of gorgeous Spanish moss trees with a private pool, sun deck, and is only a short drive...

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

Hilton Head Tours & Activities

Full Day Kayak or Canoe Rental

Hilton Head Outfitters - Bike Rental

Book online
$99.99 - $125.99

description: Single Kayak Full Day Rental: $99.99 ________________________________ Double Kayaks Full Day Rental: $125.99 _____ Duration 8 Hours (Boats must be back by 4pm each day)

Bunny Eggspress      (28 March & 4 April)

The South Carolina Railroad Museum

Book online
$25.00 - $250.00

duration: 1.5 Hours meeting_point: 110 Industrial Park Road • Winnsboro, SC 29180 description: This event is held the two Saturdays before Easter each year. Riders will board the train for a 3-mile trip to the event area. We will stop the train...

21 Day Rental

Island Life Rentals and Tours

Book online
$75.00 - $555.00

duration: 21 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...

Sunset Sport Crabbing Adventure

description: Join us for a Sport Crabbing Adventure with a sunset! Duration 2 hours About Our summer night Sport Crabbing Adventure aboard the Captain Kidd just might be the most exciting, exhilarating, and entertaining thing you do on...

Wine & Mead Tastings

Honey & Thistle

Book online
$25.00

duration: 1 Hour min_age: 21 description: Slow down, sip deeply, and savor the flavors of the land at our Wine & Mead Tasting Experience. Nestled in the heart of Harbour Town, Honey & Thistle invites you to explore small-batch wines and...

Friday Feeding Frenzy!

Coastal Discovery Museum Hilton Head

Book online
$15.00 - $20.00

description: Duration 1 Hour About TGIF ... even for our animals! Our reptiles, amphibians, fishes, and marine invertebrates all know that Friday means FRIDAY FEEDING FRENZY! Join our animal care staff and learn the ins and outs on how we care...

Sunrise Cruise

Flip Flop Charters

Book online
$895.00

description: Limited Availability! Duration 2 hours About There are few things as beautiful as a Hilton Head sunrise. Every morning we’re greeted with the most brilliant colors as the sun makes its way over the horizon. Join us for a ...

Sunrise Beach Photography

Island Life HH Photography

Book online
$225.00 - $775.00

duration: Up to 60 minutes cancellation_summary: Full refund if we cancel due to weather; no refund or discount for late arrival meeting_point: 55 Starfish Dr, Hilton Head Island, SC 29928 description: Get your photo taken on the beautiful Hilton...

Beach Gear Rental • Four Days

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

description: Everything you need for a fun and comfortable day at the beach! Duration 4 Days About - Free delivery and pickup - Beach gear is delivered the morning after check-in and will be picked up the night before check-out no later than...

Dolphins, Sharks & Shells!

Dolphin Discoveries Hilton Head

Book online
$475.00 - $845.00

duration: 3 to 6 Hours cancellation_summary: Up to 48 hours Before w/ No Questions Asked. If rain or weather does not allow us to get out, we reschedule or refund(up to you). meeting_point: Broad Creek Marina - End of wooden pier, at sign, above...

Private Dolphin Tour

Cross Island Cruises

Book online
$279.00

duration: 90-105 minutes meeting_point: 68 Helmsman Way group_size: Maximum 6 people pricing: $269 total, for up to 6 passengers per boat. No hidden fees! description: On a private dolphin tour, guests can expect a personalized and up-close...

Outside DMC Partner Outing - Palmetto Bluff Departure

description: *MUSIC | FOOD | FUN | & MORE* Outside DMC invites our partners to showcase Outside's OHANA & PAGE ISLAND! Join us for music, food, games, and more, and learn about the ultimate destination experience for your clients! Check-in will...

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