Hilton Head, SC Vacations

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Find your perfect Hilton Head

Vacation Rental

Featured Vacation Rentals

3rd Floor Condo with pools, tennis/pickl...

Spa On Port Royal Sound 1322Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your serene hideaway in Hilton Head Island! This freshly updated condo...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
2 Min Walk 2 Beach. Walk 2 Pickleball Go...

2 weeks in April and 1 week in July only open dates for next 6 months. One of the Finest-Located Homes on Hilton Head Island! Savor a true island hideaway at this gorgeously appointed third-row ocean home in Palmetto Dunes Plantation, just a...

  • Hilton Head
  • 5 Bedrooms
  • 3 Bathrooms
  • Sleeps 12
Ideal Hilton Head vacation rental for fa...

This Hilton Head Island home rental features an open floor plan that is ideal for family gatherings - and you'll adore the private pool! The dining room has seating for eight and a wall of windows flanking a French door that opens to the outside...

  • Hilton Head
  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 12
Well-equipped condo w/furnished balcony,...

Sea Side Villas I 308Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'This third-floor condo is ideal for a hideaway to the beach–it comes equipped with all...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
Lagoon views, shared pool and easy acces...

Anchorage 7444 - Blue OasisOur calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the heart of Hilton Head Island, this striking condo offers an abundance...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
Charming Hilton Head Island Vacation Ret...

Welcome to your ideal hideaway! This gorgeously appointed 1-bedroom, 1.5-bath Hilton Head Island vacation rental offers a serene escape with modern amenities and inviting outdoor spaces.Step into a bright and airy living area featuring chic...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 2

Hilton Head Tours & Activities

Valentines Nature Art for Kids

Hilton Head Island Recreation Association

Book online
$25.00

duration: 1.5hrs meeting_point: Island Recreation Center, 20 Wilborn Rd, Hilton Head Island, SC 29926 group_size: Maximum 20 people description: Come join Moore To Life and Island Rec Center for a holiday craft day. Give the gift of nature. Whether...

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...

Baby Gear Rental Package • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$220.00 - $280.00

duration: 7 Days cancellation_summary: Cancellations must be received a minimum of 72 hours in advance to be considered for a refund. meeting_point: A member of our staff will reach out with the contact information provided to confirm the rental...

10 Day Rental

Island Life Rentals and Tours

Book online
$42.00 - $295.00

duration: 10 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...

Private Morning Sail and Dolphin watch on Knot The Office
Book online
$315.00 - $395.00

duration: 2 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 6 passengers accessibility: Limited Handicap accessibility, Please call us to ensure we...

Sunset Glow Bike Tour

Glow Bikes Hilton Head

Book online
$38.25 - $45.00

description: Experience the breathtaking beauty of the Sunset Tour on our Glowing Bicycles! Duration 35 minutes About Join us for a mesmerizing 35-minute Sunset Tour while riding on glowing bicycles! Witness the enchanting beauty of Hilton...

Two Week Electric Bike Rental

Hilton Head Bicycle Company

Book online
$100.00 - $475.00

description: Electric Bike Rental Duration 14 Days About Priority E-Coast. These e-bikes are designed to go anywhere. They are designed to fit anyone from 5'2-6'6. The Standard Step-Thru makes it easier to get on and get going -- all...

Private Beach Sail On Hobie Catamarans

Hilton Head Island Recreation Association

Book online
$275.00

duration: 1.5 hours meeting_point: Sea Pines Beach Club, 87 N Sea Pines Dr, Hilton Head Island, SC 29928 group_size: Up to 4 people description: 1.5 hour, up to 4 participants. Take a ride on our 17’ Hobie Getaway with one of our US Sailing...

Daily Clinics

Palmetto Dunes Golf Academy

Book online
$50.00

Learn something new every day! Duration 50 minutes About The Academy presents a daily golf clinic at the Arthur Hills Golf Course, featuring special instruction on the stroke of the day. With a student-instructor ratio of 5:1, you can be sure...

Sound Explorer Kayak Camp

Port Royal Sound Foundation

Book online
$400.00

duration: 7 Hours cancellation_summary: Due to limited space and high demand for our Junior Pluff Mudder summer Camps, all payments are non-refundable. Please let us know as soon as possible if you have to cancel your reservation so we can fill your...

Three Week Bicycle Rentals

Forest Beach Surf & Cycle

Book online
$60.00 - $300.00

description: Rent with us! Duration 21 days About Forest beach surf & cycle is your source for Hilton Head Island bike rentals. We have bikes for kids and adults of all ages, sizes and skill levels, as well as specialty bikes and...

Private Sunset Sail and dolphin watch on Seas The Moment - newest vessel

duration: 2–2.5 hours cancellation_summary: 72 hour free cancellation meeting_point: 1 waterway lane, Hilton Head Island, SC 29926 max_age: 90 group_size: Maximum of 12 people accessibility: Limited Handicap accessibility, Please call us to ensure...

Find your perfect Hilton Head

Fishing Charter

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