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Charleston Vacation Rentals

Locally Owned and Managed Vacation Homes You Can Trust

The welcoming community spirit, history, and incredible food scene in Charleston, SC are among the many factors that make this endearing, iconic southern port rank regularly among the world’s top travel destinations.

As part of Roofstock, Matt McChesney and the Charleston Casago team bring national resources and expertise while keeping everything rooted in the Lowcountry community. Their local expertise underscores a deep appreciation for the history, charm, and hospitality that make Charleston unique.

This appreciation extends to ensuring that guests experience the best of Charleston, while the team prides itself on supporting its owners with trusted, hands-on care. The benefit of Roofstock’s scale, blended with a true local presence, makes for memorable stays and long-lasting partnerships.

Welcome to Charleston!

The cobblestone streets, horse-drawn carriages, and sun-kissed beaches of Charleston make it one of the South’s most iconic destinations. From its picturesque seawall and walkway along Rainbow Row at the Battery, to King’s Street shops on a pleasant afternoon, Charleston is where utmost beauty blends with Southern hospitality.

Starting in 2013, and for over a decade, Charleston was named the top travel destination in the U.S. There’s no question the city continues to charm visitors from across the globe, welcoming 7 million people yearly.

Families, couples, and history buffs are consistently drawn to this port as Charleston is a cultural hotspot on South Carolina’s east coast, and the state’s largest city. Located in Lowcountry, Charleston is known as The Holy City, given its historic tolerance for religions of all types. A steeple-clad skyline further reflects the city’s moniker.

Founded in 1670 by English colonists as Charles Towne, this quintessential southern belle has historically figured through the Revolutionary and Civil Wars. It is also home to a legacy of rice and cotton plantations, pirate lore, and inviting parks.

Charleston’s rich history, antebellum and modern architecture, along with exciting family-friendly attractions, means there’s something for everyone. Take time to enjoy Charleston’s world-class golf or explore its walkable neighborhoods and savory cuisine. You’ll quickly see why Charleston is known as one of the most beautiful cities in the world.

FAQs about Charleston

  • Spring and Fall in Charleston are attractive for their mild weather, blooming gardens, and festivals. These temps coincide with the High seasons, which are generally March – May as well as September – November. Summers in Charleston tend to be hot and humid, while winter is also a less crowded season – except for the holidays. Still, it’s always a good time to visit Charleston.

  • Charleston’s rich heritage can be seen in its architecture, surrounding plantations and gardens, and historic forts.

    • The Battery – Historic seawall along the southern tip of Charleston. It’s a fantastic spot for strolls to enjoy the city’s charm, and nearby Rainbow Row.
    • Fort Sumter & Fort Moultrie – Located in the middle of Charleston Harbor, Fort Sumter is accessible only by ferry. Built on a man-made island in the early 1800s, Fort Sumter played a pivotal role in the Civil War, including the first shots of the war. Today, this historic site welcomes visitors for talks and exhibits exploring the fort’s history and importance. Fort Moultrie, the predecessor to Fort Sumter, is located within the same National Park.
    • USS Yorktown at Patriot’s Point – This is a popular Lowcountry attraction for history aficionados of all ages. Located just across Charleston Harbor from downtown Charleston.
    • Magnolia Plantations & Garden – Respectfully showcasing the storied past and present of Charleston, this is considered to be one of the largest gardens in the country. It is one of six plantations to visit in the Charleston area. The poignant plantation also has preserved cabins on the property, where enslaved families lived from 1850 until the late 20th

    • The beaches at Sullivan’s Island – This family-friendly spot sits at the mouth of the Charleston Harbor and is only 10 miles east of downtown. You’ll find several beaches, plus a wide offering of restaurants and shopping along here.
    • Folly Beach – About 15 miles south of downtown Charleston, offering a 6-mile stretch of coast. Great for a day trip, plus offers several restaurants and bars.
    • Isle of Palms beach – Charleston’s other closest shoreline is located north of the city, also about 15 miles from downtown. There aren’t as many restaurants and bars as Folly Beach, though with 7-miles of beach it is a great spot for activities on the water, or just sunbathing for a relaxed beach day.

  • Charleston is alive with festivals and attractions year-round. Some of the most notable include:

    • Spoleto Festival USA (May/June) – The country’s premiere performing arts festival which takes place over a period of 17 days at the end of May into early June. Nearby festivities complement the major festival, including the Piccolo Spoleto Festival
    • Charleston Wine + Food Festival (March)
    • Southeastern Wildlife Exposition (SEWE) (February)
    • Lowcountry Oyster Festival (January)
    • Charleston Jazz Festival (mid April)
    • Holiday Festival of Lights (Nov – Dec)