Hilton Head, SC Vacations

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Vacation Rental

Featured Vacation Rentals

Water-view townhome with pool & tennis a...

Summary:Townhouse Manor 6The Space:This fresh Shipyard townhouse offers a comfortable, refreshed home base just a short walk from all the best Hilton Head has to offer. Golfers in the group will appreciate the location, just off the greens of the...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Prime location w/ private pool, elevator...

Summary:Curlew 8The Space:Curlew 8 is a opulent second-row private home featuring ocean vistas and chic, coastal décor. This modren private home in North Forest Beach is roomy and inviting - it was freshly remodeled and everything has been brought...

  • Hilton Head
  • 7 Bedrooms
  • 6 Bathrooms
  • Sleeps 28
Oceanfront resort condo with WiFi, balco...

Summary:Sea Side Villas II 252The Space:Serenity by the sea awaits at this one-bedroom condo at Sea Side Villas! Centrally located steps from Coligny Beach Park and Plaza, this complex features an on-site pool, grille areas, a sun deck, and direct...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Seas the Day - all-suite getaway with po...

Summary:Fiddlers Cove 21HThe Space:Charmingly refreshed, Seas the Day offers a extravagant all-suite layout and a prime mid-island location just 300 yards from the beach. Leisurely days are spent appreciating the striking on-site amenities...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
Third Row Private Home with Large Privat...

Handsomely appointed, this appealing 3-bedroom Hilton Head Island home is in an superb third-row location, just a short walk (about 3 mins.) to the beach! The home is also only a leisurely walk or bicycle ride away from all that Palmetto Dunes has...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
Sunset Rentals | Tennismaster 904

If you’re looking for a handsome and convenient Hilton Head rental condo, you have no choice but to savor your stay at this astounding 3 bedroom, 3.5 bathroom end unit Tennismaster villa in the heart of Shipyard, Hilton Head Island.As you enter...

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

Hilton Head Tours & Activities

Three Hour Beach Combing and Dolphin Nature Watch Tour
Book online
$375.00 - $415.00

description: *Perfect for those who like to venture off the beaten path!* ___________________________________ Rates **Up to Four Guests** - $375.00 **Five Guests** - $385.00 **Six Guests** - $395.00 ***All ages welcome! | Maximum of 1200...

Gift Card

Wheelz of Hilton Head

description: Purchase the perfect gift: a gift card with a value of your choosing!

Bike Rental • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$20.00 - $100.00

duration: 7 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: Confirmation will include your lock combination in addition to delivery and pick up...

Baby Gear Rental • Six Days

Lowsea Bike, Beach and Baby Rental

Book online
$15.00 - $175.00

description: Don't pack it, Rent it! Baby Sleep, Feed, and Play necessities for your vacation! Duration 6 Days About All baby gear rentals include: - Free delivery, setup & pickup - Linens washed in baby detergent to keep your baby clean and...

Island Happy Hour Cruise

Daniel Island Ferry

Book online
$18.00 - $38.00

duration: 75 minutes meeting_point: description: Friday Happy Hour Cruise on the Wando River Every Friday | 4:00 PM – 5:15 PM Start your weekend on the water aboard Daniel Island Ferry's Friday Happy Hour Cruise. This relaxing 75-minute cruise...

Bike Rental • Two Weeks

Lowsea Bike, Beach and Baby Rental

Book online
$40.00 - $200.00

duration: 14 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

Fireworks Cruise Aboard Dolphin Seafari
Book online
$35.00 - $50.00

duration: Approx. 2 hours cancellation_summary: Full refund if canceled 24 hours or more before the tour; call 843-785-2345 for cancellations or changes. group_size: Maximum 20 passengers accessibility: Handicapped accessible; guests should call...

Private Dolphin Tour

Lowcountry Watersports

Book online
$329.00 - $479.00

duration: 1.5 hours cancellation_summary: Cancellations allowed up to 48 hours prior; no refunds within 48 hours. meeting_point: Palmetto Bay Marina – 86 Helmsman Way Suite 101, Hilton Head, SC 29928 min_age: 9 max_age: 99 group_size: Maximum 14...

Marriott Vacation Club Daufuskie Tour

meeting_point: Hilton Head Island, SC description: Tucked between Hilton Head and Savannah, and only accessible by boat, Daufuskie is a must-see in the Lowcountry!

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...

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...

10 Day Rental (Walk Up)

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 Days description: Same Day Reservation Pick Up Procedures Business hours are 9am to 4pm. Same day reservations may pick up **anytime** after you book. It does not need to be 4pm. After hours self pick up and drop off available...

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