Hilton Head, SC Vacations

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Featured Vacation Rentals

Just off the ocean, beachside pool & hot...

Have the quintessential island hideaway at this handsome 1-bedroom, 1.5 bath Barrington Park villa inside Hilton Head’s premier Palmetto Dunes Resort! This unit is a hop and a skip (3 min. walk) from the beach, and the complex features one of the...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 4
Large Three Bedroom Villa Steps from the...

This three bedroom, three bathroom villa will be ideal for next family or group outing! Steps from the pool and mere mins. from the beach, this enormous villa will provide ample space for your family to spread out and relax!The kitchen has been...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 8
3133 Villamare - Direct Oceanfront Views...

This charmingly refreshed 3 bedroom, first floor corner villa offers gorgeous ocean vistas from every room and was thoughtfully refreshed in 2026. Updates include new furnishings in the living and dining areas, updated floor throughout the main...

  • Hilton Head
  • 3 Bedrooms
  • 3 Bathrooms
  • Sleeps 9
Steps from the Sand: Beautiful Oceanfron...

Welcome to Island Time y'all! Ocean Dunes, your ideal family hideaway on Hilton Head Island! This appealing villa offers a gorgeous oceanfront view where you can savor your morning coffee on the balcony while watching the sunrise. Savor direct beach...

  • Hilton Head
  • 1 Bedrooms
  • 1 Bathrooms
  • Sleeps 6
Short walk to golf courses, pool and bea...

Feel the ideal blend of comfort and convenience in this impressive Hilton Head vacation rental. Whether you're cooking a delicious meal for your family or group, the completely equipped kitchen has everything you need. It features a Keurig coffee...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 8
Amazing pools, hot tub, and oceanfront v...

Villamare 3425Our calendar is refreshed in real-time & our nightly prices are accurately displayed. Simply enter your desired dates and click 'Book Now!'Appreciate your breakfast and coffee from your shaded balcony while taking in the vibrant...

  • Hilton Head
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6

Hilton Head Tours & Activities

Baby Gear Rental Package • One Week

Lowsea Bike, Beach and Baby Rental

Book online
$245.00 - $305.00

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...

Single Kayak Rental

Wateree Marina

Book online
$25.00 - $50.00

description: Single Kayak Rentals What to Bring - Valid Driver's License - Major Credit Card

Dolphin Eco Tour

Captain Moto Adventures

Book online
$325.00

description: Duration 2 Hours About Not just your everyday dolphin tour. This is a private tour for the family. Learn about the local ego system and see dolphins. What to bring - BYOB - Sunglass - Sunscreen *No spray lotion* ...

One Day Beach Wagon Rental

Hilton Head Outfitters - Bike Rental

Book online
$21.99

description: **This item is NOT available for delivery and MUST be picked up/returned to 80 Queens Folly.** Carry everything you need to the beach. Extra large wheels make it easy to pull in the sand. Convenient cup holders and pouch inside to hold...

Pontoon Boat Rental

Lowcountry Watersports

Book online
$270.00 - $625.00

duration: 2 Hour, 3 Hour, 4 Hour or 6 Hour 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 group_size: **Maximum of 10...

Two Hour Dolphin Nature Cruise

Hilton Head Island Tours

Book online
$250.00

description: *Enjoy your 2 Hour Dolphin Nature Cruise!* ___________________________________ Rates **Private Charter** - $250.00 ***All ages welcome! | Maximum of 1200 lbs*** ___________________________________ About your Fishing Trip: ...

SC Pimento Cheese Festival- Vendor
Book online
$30.00 - $125.00

duration: 8 hours meeting_point: 6071 St Andrews Rd, Columbia, SC 29212 description: With over 2,500 in attendance in our 1st SC Pimento Cheese Fest last year, we believe this year will be bigger and better! Promote your business in front of the...

Four Hour Inshore/Nearshore Fishing Trip

Hilton Head Island Tours

Book online
$605.00 - $655.00

description: *Four Hour Inshore Fishing Trip* ___________________________________ Rates **Up to Four Guests** - $545.00 **Five Guests** - $575.00 **Six Guests** - $595.00 ***All ages welcome! | Maximum of 1200...

Equestrian Lessons - Palmetto Bluff Members

duration: 1 hour meeting_point: Activity Barn Longfield Stables 24 Healey Rd, Bluffton 29910 SC min_age: 6 group_size: Private or semi private description: Whether you're a first-time rider or looking to refine your skills, our equestrian lessons...

Private Inshore Charter Fishing aboard Hobo
Book online
$440.00 - $540.00

duration: 3 Hours cancellation_summary: 48 hours meeting_point: Drifter Excursions, 86 Helmsman Way, Palmetto Bay Marina group_size: Licensed for up to 16 passengers; rate includes 6 passengers pricing: - **Two-Hour Charter** - *$440* - Includes 6...

Luxury Pontoon Rental with Fireworks Experience

description: Fireworks Pontoon Party Boat Rental and private VIP box for Harbourfest Fireworks Show! Captain your own adventure as you head out on a 2-hour self-guided cruise on a luxurious Bentley pontoon boat. Return to Shelter Cove Marina no...

Cocktails & Camellias

Coastal Discovery Museum Hilton Head

Book online
$200.00

duration: 3 hours meeting_point: 70 Honey Horn Dr, Hilton Head Island, SC min_age: 21 accessibility: Wheelchair accessible description: Immerse yourself in the beauty of the Lowcountry at *Cocktails & Camellias*, an elegant evening set against the...

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