History of Hilton Head Island


Situated only 45 minutes from historic Savannah, Hilton Head is the largest of the South Carolina islands stretching 12 miles along the Atlantic Coastline. Hilton Head Island offers the ultimate in Lowcountry island living – miles of unspoiled beaches, nature preserves and biking trails, world-class golf and tennis, upscale shopping and dining, and luxury Lowcountry coastal retreats. 

Hilton Head Island also offers visitors a glimpse into the fascinating history of South Carolina’s Lowcountry, a destination that has survived three wars, multiple hurricanes, and eras of feast, famine – and fame. In 2021, Travel+Leisure ranked Hilton Head #1 in World’s Best Islands but what lies behind the fame of America’s favorite island. Journey with us as we explore the fascinating history behind Hilton Head Island.


2000 BC to 1500 AD

Evidence of life over 4,000 years ago remains on Hilton Head Island today. The well-preserved Native American Indian Shell Ring is located in Sea Pines Preserve and is the oldest known archaeological site on Hilton Head Island, and one of only 50 shell rings known to still exist today. This iconic remnant of Hilton Head Island’s history measures 150 feet in diameter and is one of the most pristine examples of a shell ring remaining in the USA. 

Later, in 1335 A.D, the Native American tribes built a fortified village covering two acres along the banks of Skull Creek. This shell ring is also open to the public on a short and easy trail at the Green’s Shell Enclosure Heritage Preserve. Both these historic shell rings are today listed in the National Register of Historic Places.


1500 to 1700: EARLY EUROPEAN EXPLORERS

Historical records show the first Spanish explorers making contact with local Native Americans in 1521, nearly two hundred years later. In 1566, the Spanish explorers built Santa Elena, a permanent settlement and Fort across the Port Royal Sound on Parris Island. They abandoned Santa Elena in 1587 to colonize further south in St Augustine, Florida. By 1663, the island was largely uninhabited except for a small population of Native Americans living off the land. 

In August 1663, English Captain William Hilton set sail from Barbados to explore land granted to the Lords Proprietors, eight Englishmen to whom King Charles II had granted power of Carolina. His original landing site was the Port Royal Sound and, on gaining first sight of the headlands, he claimed the land for Britain. 

In the spring of 1670, Captain Robert Sandford together with over 150 colonists, servants and slaves sailed into what is today Charleston Harbor claiming the land and naming it Charles Town, in honor of King Charles II. By 1672, the expanding settlement had relocated on a peninsula between the Cooper and Ashley River and …. the rest is history! Today, Charleston ranks as the #1 City in the USA

On 16 August 1698, the Lords Proprietors granted John Bayley of Ireland a barony which included most of Hilton Head Island, excluding Port Royal Sound and Skull Creek. John Bayley never once visited Hilton Head Island, instead appointed Alexander Trench as an agent to sell the property. The bulk of the barony remained in the Bayley family until after the Revolutionary War.


1700 to 1860: HILTON HEAD PLANTATION HISTORY

In 1717, Colonel John Barnwell was granted 1,000 acres of land on the NW corner of the island (now Hilton Head Plantation) and became the first white settler on Hilton Head. There was still hostility between the Spanish and British and, in 1733, the City of Savannah was founded as a barrier between Spanish Florida and British Carolina. 

By the 1750s, most of the plantations on the island were successfully growing indigo, which was being sold to the English – until the Revolutionary War. During the Revolutionary War (1775 to 1783), the British successfully took the city of Savannah (after failing to take Charleston!) and frequently raided the island, burning plantations and capturing slaves. Aside from rice, indigo was South Carolina’s most second valuable export, however trading with England had now ceased. 

It wasn’t until 1790 when William Elliott planted the first crop of Sea Island long-staple cotton that the island once again began to gain recognition. William Elliott teamed up with neighbor Will Seabrook to pioneer a new fertilizer for the cotton crops and the Lowcountry sea islands began to boom. 

The War of 1812 brought more devastation by British forces to the island, but the economy quickly resumed and, by 1860, the cotton industry on the island was lucrative with nearly two dozen working plantations.


1860 to 1940: SLAVERY & THE CIVIL WAR

South Carolina was the first US state to withdraw from the Union in December 1860, and, in April 1861, the Civil War began. After the Battle of Port Royal Sound in November 1861, more than 12,000 soldiers captured Fort Walker and Hilton Head Island fell into the hands of the Federal troops. Hilton Head Island became the headquarters for the blockade of the South Atlantic coast with an estimated forty thousand soldiers, prisoners of war, and former slaves settling on the island. The prospering rice, indigo and cotton plantations were abandoned, yet this victory meant freedom for the African Americans that remained. 

In 1862, Union General Ormsby Mitchel built the town of Mitchelville, the first self-governing town of formerly enslaved African Americans with nearly 1,500 Gullah residents. Land was confiscated, northern missionaries opened one room schools, and homes were built for the former slaves, known locally as “contrabands of war”. 

In 1864, as the troops began to move out of the area, Fort Howell was built to protect the town of Mitchelville. In 1865, the 13th Amendment to abolish slavery was signed and the Gullah community of Mitchelville were legally freed. Many moved on, others stayed on the island farming in the summer, oyster harvesting in the winter, and remaining true to the rich legacy of the Gullah culture. 

Hilton Head Island returned to nature and from the 1900s to 1950s was primarily used as a destination for wealthy private hunting groups. Today, visitors to Hilton Head can walk the quiet trails leading through historic Mitchelville Freedom Park with the original site of Battle of Port Royal, historical remnants of the town and Fort Howell, and access to an off the beaten path beach overlooking the passage taken by Captain William Hilton in 1663. 

The Baynard Plantation, built by Revolutionary War hero Captain Jack Stoney in 1793, was used as the HQ for the Union troops and was later burned to the ground. Visitors to the island today can still tour the ruins of the grand antebellum home and slave quarters on a short hike through Sea Pines Preserve.


1950 to 2000: MODERN AGE OF HILTON HEAD ISLAND

By early 1950, Georgia timberman Fred Hack had discovered the acres of loblolly pine and live oak trees on Hilton Head and, along with JB Fraser and other investors, set up the Hilton Head Company and began to buy up acres of land to harvest lumber. Lumber mills were built and, after harvesting millions of feet of lumber, Hilton Head Company began selling off lots along the beach for vacation cottages.

The modern age of Hilton Head Island began with Charles Fraser, son of J. B Fraser. Charles had a vision to preserve the plantation history and natural beauty of the island and build an eco-friendly, resort community on his family land dominating the southern tip of the island. The first car ferry arrived in 1953, a grocery store opened at Coligny Circle in Forest Beach, and the James F. Byrnes swinging bridge was built in 1956, finally connecting Hilton Head Island to the mainland. 

Fraser’s vision for a world-class resort became a reality and a model for future resort communities across the US. Sea Pines Plantation was a stunning natural oasis with classic Lowcountry architecture and beach homes, untouched forest preserves, 5-miles of sandy beaches, championship golf courses, and the signature candy-cane Harbour Town Lighthouse. Shipyard was the second plantation to be developed on Hilton Head, followed by Port Royal and Palmetto Dunes


EXPERIENCE HILTON HEAD ISLAND’S HISTORY

Harbour Town Lighthouse

Hilton Head Island is home to two lighthouses: The historic Leamington Lighthouse built by Union Troops in 1879 which overlooks the Arthur Hills Golf Course in Palmetto Dunes and the iconic Harbour Town Lighthouse in Sea Pines Plantation, built by Charles Fraser as a fun and memorable landmark and museum dedicated to the history of Hilton Head Island. The 90-ft lighthouse features ten levels of fascinating photos and artifacts, a Coast Guard Exhibit, a one-of-a-kind gift shop and views all the way to Tybee Island!

Coastal Discovery Museum

The Coastal Discovery Museum is situated on the historic Honey Horn plantation, dating back to before the Civil War. The museum is home to nine historical buildings, the Santa Elena Center highlighting the history of 16th century Hilton Head, and 68 acres of beautiful grounds with nature trails, butterfly gardens, and an ancient 500-year old Southern Red Cedar. The Coastal Discovery Museum offers guided history tours of Hilton Head Island, the Forts of Port Royal and the habitats and history of Pinckney Island.

Venture beyond Hilton Head Island to learn more about the history of the Gullah culture on a boat tour of Daufuskie Island or take a cruise of Savannah’s historic port and riverfront.

Local Tip: For traditional Gullah-Geechee cuisine, soulful blues, and warm southern hospitality, stop by Ruby Lee’s situated just across William Hilton Parkway!

Port Royal Golf Club

Tee off for a round of golf at the Robber’s Row Course set atop former civil war grounds with interpretive markers on several holes describing the historic events that took place at Port Royal.

Gullah Heritage Tours

Travel through the communities of Hilton Head Island on a two-hour narrated bus tour with native Gullah residents. The tour is fun, interactive and covers the top historic Gullah attractions on the island including the Gullah Museum, a tiny museum dedicated to preserving the Gullah-Geechee heritage and culture. 


Locally serving Hilton Head since 1993, Sunset Rentals are one of the most experienced vacation rental companies on Hilton Head Island. Our portfolio of 220+ vacation homes and villas are situated in the top resort areas of Hilton Head Island with luxury vacation amenities and a 24/7 guest concierge from our local team. 

Take a tour of the resort areas of Hilton Head Island, browse our collection of luxury rentals (many including bike & beach gear credit valued up to $350!), and book your vacation with confidence and ease with Sunset Rentals.


Shop at Lowcountry Farmers Markets


Support local businesses here in the Lowcountry by visiting a Farmers Market to stock up on fresh groceries and new products. Whether you’re looking to pick up some dinner items for a home cooked meal in your vacation rental or wanting to bring home some knowledge and practice, a Farmers Market is the perfect place to visit on your next vacation to Hilton Head Island!

Hilton Head Farmers Market

The Hilton Head Farmers Market is held every Tuesday from 9:00 AM to 1:00 PM at the Coastal Discovery Museum’s Honey Horn campus. Stop by to purchase local produce, seafood, meats and more while you enjoy unique vendors, food trucks, and live entertainment.

The Farmers & Makers Market

Every Tuesday starting March 15th through November 22nd, from 10:00 AM to 2:00 PM at The Shops at Sea Pines Center. You can find seasonal fruits and vegetables, freshly caught seafood, baked goods, barbecue, and artisan crafts!

Bluffton Farmers Market

Open every Thursday from 12:00 PM to 4:00 PM. Hours and days vary, please check the Bluffton website for updated details. Enjoy fresh produce, prepared foods, plants, family-friendly activities, and live entertainment.

Lowcountry Made Popup Artisan Markets

The Made Market takes place every first and third Sunday starting in March through December, from 9:00 AM to 1:00 PM. The Night Bazaar takes place every first Thursday from March through July and October through December, from 5:00 PM to 8:00 PM. These popup markets feature local artisans, small businesses, live entertainment, food, and drinks.

The Root and Bloom Market

A year round market every Saturday from 9:00 AM to 12:00 PM. Enjoy local organic produce and learn about the impact your health can have on your physical and emotional wellbeing.

Port Royal Farmers Market

Every Saturday year round from 9:00 AM to 12:00 PM rain or shine. Experience fresh local produce, meats, seafood, prepared food vendors, plants, and more.

Whichever Farmers Market you find yourself at, home is just a short drive away when you stay with Sunset Rentals. With a portfolio of 220+ Hilton Head Island rentals and first class service from our on-island team, you can book your Hilton Head Island vacation home with confidence and ease at Sunset Rentals


The Perfect Place to Spend the Holidays in South Carolina

Call Hilton Head Home for the Holidays

There’s no better place to visit during the holidays in South Carolina than Hilton Head Island. To say Hilton Head Island has holiday cheer and spirit is an understatement. This charming South Carolina island has tons of great holiday events and activities for tourists and locals to enjoy. 

At Sunset Rentals, we want you to get the most out of your holiday getaway to Hilton Head Island. To help you plan your trip, we’ve compiled a guide on the best holiday events Hilton Head Island has to offer.


Holiday Events on Hilton Head Island

Hilton Head Island is chock-full of holiday-related events! Whether you’re looking to give back to the community, learn some holiday recipes, or enjoy a holiday light show, Hilton Head Island has an event for everyone.

  • Riverside Holiday Bizarre: Browse goods from local vendors and get entered to win a prize in a raffle at this annual holiday bizarre. Each family gets one entry, and you can score additional entries by donating toys to Toys for Tots.
  • Holiday Market: Head to the Coastal Discovery Museum for three days of the holiday market. You’ll enjoy food sampling, a chance to meet a variety of authors, and purchase handmade ornaments.
  • Visit Santa: Take the kids to meet Mr. and Mrs. Claus at the Shelter Cove Towne Centre starting the day after Thanksgiving. Don’t forget to bring your camera!
  • Tree Lighting Ceremony & Santa’s Workshop: Head to Martin Family Park in Bluffton for the annual tree lighting ceremony. Afterward, head to DuBois Park to meet Santa.
  • Harbour Town Lights: Perhaps the most well-known holiday tradition of all in Hilton Head Island is the Harbour Town Lights. Stroll through iconic Harbour Town, taking in the beautiful holiday lights and massive Christmas tree. The lighting ceremony takes place the day after Thanksgiving and features plenty of live entertainment and activities. If you can’t make it to the lighting ceremony, the Harbour Town Lights will remain lit the rest of the holiday season.

Enjoy the Holidays in Hilton Head Island, South Carolina

Hilton Head Island is the best place in South Carolina to spend the holidays! On top of all of the great holiday events you can enjoy, you can also enjoy the holidays at the beach, playing at some of the nation’s best golf courses, or dining at some of the island’s best restaurants.

Sunset Rentals has plenty of excellent vacation home rentals perfect for your holiday getaway to Hilton Head Island. We’ve compiled a list of featured vacation homes for the holidays. To book your stay with us, please check availability online or give us a call at 843-785-6767.

Hilton Head Ranked #1 in World’s Best Islands

This year’s World’s Best Awards was published on September 8, 2021 by Travel + Leisure. A repeat favorite, Hilton Head Island was ranked #1 on the list – read the full article here.

“With 12 miles of pristine beaches, 33 golf courses, 60 miles of walking trails, as well as outstanding restaurants, museums and galleries, this South Carolina island has been popular with voters for years. For longer stays, many visitors choose to rent houses […] “We can be as busy as we like or just relax and take in all the beautiful beaches and sea life,” said one voter.” – Travel + Leisure

Stay with Sunset Rentals and see what Hilton Head Island has to offer for your next coastal vacation! You’ll understand why readers continue to vote for it as the best island in the United States.


Featured Vacation Rentals

Explore available vacation homes and villas offered by Sunset Rentals:

TURTLE LANE 19 – Spacious, updated 4 bedroom Turtle Lane townhome with community pool access!
KINGSTON 36 – Stunning private, dog-friendly home in Shipyard Plantation with private pool!
OCEAN ONE 121 – Picturesque 3 bedroom oceanfront villa, close to Coligny with pool access!

The Best Sea Pines Vacation Rentals in Hilton Head Island

This beloved South Carolina destination has been a popular vacation choice for generations. There’s so much to do here! A Sea Pines getaway is as relaxed, or as active, as you make it. The team at Sunset Rentals is on-hand to help you find an idyllic vacation rental in Hilton Head’s Sea Pines community that suits your aesthetic tastes and budget. And we’ve also pulled together a list of some of the best things to do on Hilton Head during your stay.

Tee Off

Hilton Head Island is a golf lover’s paradise—it’s a PGA Tour event destination and home to more than 24 championship courses! Sea Pines has three premier courses, including Harbour Town Golf Links, which was named one of the top 20 courses in the country. If you’re a keen golfer, what better way to start the day than with views over the Atlantic Dunes Golf Course from our two-bedroom, two-bathroom Plantation Club Villa 533.

Wine and Dine

Head into picturesque Harbour Town to sample a range of culinary offerings. Why not treat yourself to some of the best local produce at CQs, which is housed in Harbour Town’s first-ever building. Our three-bedroom, three-bathroom Ketch Court Villa is conveniently located close to town, so you won’t have far to travel at the end of the night. 

Family Fun

Hilton Head Island is the ideal location for a family beach vacation. South Beach is a great place for collecting shells—and spotting dolphins! Why not book one of our newly-renovated two-bedroom Beachside Tennis Villas down at South Beach, where there’s a good chance you’ll spot some of those gorgeous marine mammals over breakfast!


The Best Collection of Sea Pines Vacation Rentals

At Sunset Rentals, our Sea Pines properties range from two-bedroom villas to seven-bedroom homes. For peace of mind, all our properties feature high-security keyless entry, and our premium Sea Pines rentals include luxury linen and towels. Let us help to plan your next Sea Pines stay!


Rent a Boat on Beautiful Hilton Head Island

Hilton Head Island is blessed with 12 miles of coastline along South Carolina’s Atlantic coastline, making it perfect for fishing, boating, and tons of water sport activities. There are various opportunities to boat on several types of vehicles, like kayaks, sailboats, party boats, and even yachts. With six marinas and harbors, you will be kept busy!

Let’s explore some of the best Hilton Head boat rentals:

Island Head
Run by tourists turned locals, Michael and Taylor, Island Head boasts some of the finest Hilton Head boat rentals. Both of them have immense experience in the water sports industry, which reflects in the way they run their company. They are friendly, knowledgeable, and provide the perfect balance of fun and safety.

Anchors Away Sailing Charters
Anchors Away Sailing Charters offers private expeditions for up to six people. You can hop aboard the stunning morning sail, the breezy dolphin watch afternoon sail, or relax while viewing the sunset evening sail. All three sails have different agendas and turn out to be completely different experiences.

Vagabond Cruise
Vagabond Cruise, since 1968, is Hilton Head Island’s original sightseeing and cruise operator. Needless to say, they have tons of experience in this arena and offer some unforgettable cruises on the islands. You can take your pick from holiday cruises, crabbing expeditions, and Savannah Day cruises—amongst the many cruises they offer.

Yacht Club of Hilton Head
Founded in 1971 by a group of sailors, the Yacht Club of Hilton Head is the oldest yacht club on the island. They are a boating and social club, which means that boating enthusiasts on Hilton Island are a part of this club. They provide a variety of boating activities plus a dynamic social calendar.


HHI Vacation Rentals

If you are planning to book a Hilton Head boat rental and stay on the island, then look no further than Sunset Rentals. We provide various types of rentals to suit every family, like pet-friendly rentals, oceanfront rentals, or rentals with private pools.


Plan a Hilton Head-Style Spa Day

Hilton Head’s Best Spas

Relaxation beckons you against the backdrop of blissful harmony, nestled near the warm sunny South Carolinian beaches— all found at the finest spas of Hilton Head. After a day spent on the sandy beaches in the hot Lowcountry sun, what better way to wind down than a spa visit— Hilton Head-style. Locals and tourists alike rave about the spectacular soothing powers of the spa services provided at these staple Hilton Head spas.

Ahh Green Spa: “Relaxing by Nature” 
Mother Nature welcomes you to Ahh Green Spa, Hilton Head Island’s first-ever “green” spa, known for its signature hot stone massages. This ahh-mazing—spa comes with private rooms for all to enjoy their organic, vegan-based facials and body treatments. After a long day at the nearby world-class golf courses, treat yourself to their “19th Green” massage—for the athlete in you. 

Foundation Spa
Time spent at the Fountain Spa “is time spent in paradise.” Your 80-minute massage will feel like an eternity of head-to-toe bliss. Spa owner Vicki Economou promises that you will “love your spa treatment” or she will make it right. Their team of dedicated estheticians and massage therapists will work directly with you to build the perfect treatment experience. Join the growing list of clients who proudly boast about the amazing scents, service, and specials at Fountain Spa! 

Indigo Spa
Journey down your personal path to wellness in the Shipyard Plantation’s hidden gem, Indigo Spa—full of high-end sophistication designed by Hilton Head Health. You will never feel rushed at Indigo Spa, as they welcome you to destress in their lagoon-facing relaxation room, before and after your individualized spa treatment. Visit their sleek website now and receive 10 percent off services as a Sunset Rentals guest.


The Best Places to Stay in Hilton Head Island

At Sunset Rentals, our vacation rentals are all based in Hilton Head, South Carolina. We have some fantastic properties fit for groups of all sizes. After a day of relaxation at our island’s best spas, your blissful harmony will continue at one of our nearby properties!