Last Updated on December 4, 2023

Charming, elegant and enchanting. These are just a few words to describe Charleston, SC. The city drips with Southern hospitality and history and it’s so easy to fall in love with this beautiful Southern belle.

Charleston’s antebellum architecture is best experienced by horse-drawn carriage through the heart of the historic district. Rainbow Row, so-named for its 13 multi-hued 18th century row houses is a not-to-be-missed site. And every visitor should get to at least one of the era’s elegant plantations featured in the movies Gone With the Wind, The Patriot and the North and South mini-series.

I often say a trip to Charleston is worth it for the food alone. The city’s shrimp and grits and she-crab soup are two consistent award-winners. Innovative new restaurants popping up on the foodie scene are serving up unbelievably creative dishes.

But where to stay?

After living in Charleston for almost nine years, I highly recommend that if you’re not taking a beach vacation (yep, those beaches are amazing), you book a stay in the heart of downtown Charleston’s historic district in a vacation rental. Often more reasonably priced than a hotel room, you’ll also find more space to relax and enjoy Charleston’s sweet life.

The city is easily walkable and you’ll want to be close to the restaurants, historic attractions, antique stores and boutiques, churches and graveyards, and, of course, Charleston’s vibrant nightlife.

Here are some vacation rentals we recommend if you’re heading to The Holy City.

 Charming Old Brick Alley Home

Brick Alley Home Charleston interior.
Brick Alley Home Charleston interior. Photo courtesy of VRBO

Located at the end of a quiet cobblestone alley, this beautiful three-story home oozes Southern hospitality.

Ideal for a family or group of friends, the 2,000-square-foot abode can sleep six. The Charleston historic distric vacation rental offers three bedrooms, two-and-a-half baths, a stunningly gorgeous kitchen (for those who love to cook) and a picturesque courtyard.

Broad Street Beauty

Welcome to 19 Broad! A historic downtown vacation rental in an ideal location on the same block as the famous Rainbow Row.

The 1794 property has been fully renovated with original walls and 16-foot ceilings remaining. It features one-bedroom, one-bath, a balcony and magnificent Charleston views.

For those looking for more space, the entire property can be rented to accommodate up to eight guests. This truly is an appealing space.

Fauna House 1905 Residence

This historic property comprises the entire lower floor of a charming 1905 Charleston residence blending modern updates with preserved historical features such as original wood floors, ornamental fireplaces (non-functional), and authentic window panes.

Guests will experience the captivating ambiance of turn-of-the-century Charleston living, offering four generously sized bedrooms, two full bathrooms, and a living room with a convenient queen-sized sofa bed. The recently renovated kitchen comfortably seats eight guests and bedrooms can accommodate the same number of travelers.

Azalea’s With Private Porch

Azalea's with Private Porch vacation rental in Charleston historic district.
Azalea’s with Private Porch vacation rental in Charleston historic district. Photo courtesy of VRBO

This boho chic retreat with a private porch overlooks historic Spring Street and includes three master bedrooms, each with a king bed and ensuite bath to accommodate up to six guests.

You’ll find luxury mattresses, baths with rainfall showers, a fully stocked kitchen and a breakfast bar. Guests are only two blocks from King Street and some of Charleston’s best dining venues.

The Rainbow Cottage

This charming two-story cottage is ideal for groups of up to four guests with two bedrooms and 2.5 full baths.

You’ll find a spacious yard where you can enjoy the Southern ambiance under a grand magnolia tree. The interior of the home is luxurious and well-appointed with a laid-back “come and sit a spell” feel.

Everything about this place exudes the mood and feel of Charleston.

The Manor Guesthouse

An immaculately restored Victorian home in the heart of downtown Charleston, the Manor Guesthouse offers four bedrooms and 4.5 baths with an open living, dining and kitchen area that opens to a spacious front porch overlooking the piazza.

The magnificent home can accommodate up to 12 guests (perfect for a family reunion or friends’ getaway). To boot, it’s easily walkable to downtown eateries, historic venues, boutiques and coffee shops.

John Bulow House at St. Philip Square

Described as “pretty as a peach,” the John Bulow House was built in the late 1800s, undergoing a complete renovation in 1996.

Modern amenities blend perfectly with history and nostalgia in this three-bedroom, three-bath home that can sleep up to eight guests. And there’s that quintessential Charleston-style porch leading to a welcoming living room bathed in natural light.

Charming Studio on the Market

Studio vacation rental overlooking historic Charleston Market.
Studio vacation rental overlooking historic Charleston Market. Photo courtesy of VRBO

Love, love, love the location of this sweet one-bed, one-bath studio that’s directly across from the historic Charleston City Market.

The circa 200-year-old property was lovingly restored to honor the elegance of the yesteryear while adding necessary modern amenities. It’s ideal for a romantic weekend getaway, engagement stay, birthday surprise or anniversary celebration.

You’re not only close to the amazing market shopping, but some of Charleston’s best restaurants as well.

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