Family-friendly holiday rentals in Charleston

Historic City Charm | Private Modern Luxe

Turn back time, in this historical home, downtown Charleston, waltzing across polished wood floors past huge sash windows in a period loft. Heritage colors, design, and a mix of new and traditional pieces like an old-fashioned writing bureau add to the grandeur of 12-foot ceilings and original fireplaces. Ideal for a Couple, on a romantic getaway or a girls weekend in the top city of Charleston. Private, spacious 1,000 sq. ft. Private, off-street Parking with EV charger. Permit: OP2024-05063

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

Fire Tower 1BR/1BA - Rooftop Views!

Welcome to Fire Tower! Built in 2023, this condo building offers modern accommodations in historic downtown Charleston. Each unit features 1 king bed, 1 bathroom, and a balcony. Conveniently located off King Street, guests can easily explore notable restaurants, local shops, and entertainment venues. Amenities include off-street parking and access to Fire Tower’s shared courtyard, terrace, and rooftop—perfect for unwinding while enjoying stunning views and everything Charleston has to offer!

Modern Stylish 2b/2b Downtown near Upper King

Built circa 1887 with a full renovation completed in December 2020, this historic building boasts large rooms, 11' ceilings, original moldings, plaster and stained glass. Historic charm with modern conveniences! This 2nd floor unit with a large front porch is a close walk to great neighborhood restaurants and the upscale shopping, restaurants and bars of Upper King St. district. On site parking makes this a great home base for your stay in Charleston. The historic Market 20 min

The Garden Folly Guest House

Our architect said, “this is NOT a garage, it’s a Garden Folly!” Our Guest House has a bird’s eye view of the rose covered pecan tree and a vista of the marsh and the Wappoo Creek. When we rebuilt our 1930's garage we saved all the beaded siding and pine floor. My husband enjoyed incorporating many design elements and creative ideas. It was quickly becoming the Taj Garage. We decided it was just the kind of property we enjoy when we travel, so, Voila! we decided to share it with you!

Four Oaks Cottage at Park Circle

Experience Charleston’s hippest neighborhood in a recently renovated midcentury cottage. Walk steps to Park Circle's award-winning restaurants, or hop a 15-minute ride to downtown Charleston. Relax on the yard's tree swing after your Sullivan's Island beach day, then star gaze under hundred-year-old Lowcountry oaks. Stroll to nearby bars, breweries, distilleries, and shops in this historic, convenient, friendly, and local Charleston community. Short-Term Rental Permit 2025-0183

Large Guesthouse with Private Dock & Marsh Views

This newly built carriage house is separate from the main house. The cottage is about 1,200 sqft so it very open and spacious and great views of marsh and our tidal creek. We have a separate work area with desk and a massive dinning table if you need more room to work or to gather with friends. Full kitchen, washer and dryer, massive shower, the list goes on. You may not want to leave! Feel free to go sit and have coffee or cocktails on the dock. PERMIT# OP2024-04998

Newly Renovated Guest Suite with Exterior Entrance

Stay in one of Charleston's few legally permitted AirBnB properties located just minutes from downtown Charleston, SC. You will find our spacious, newly renovated 1 bedroom guest suite with it's own exterior entrance perfect for your trip to Charleston. Enjoy amenities such as a Kuerig with complimentary coffee, microwave and fridge . Folly Beach is also a short drive from the old well established neighborhood you will be in. City of Charleston Permit 05732.

The Retreat. Quiet. Private Yard. Walk to King

A calm oasis in the city, set back from the street. Dine under backyard palms, a rare find downtown, or enjoy morning coffee on the porch. - 5-min walk to King St - Your own private back yard! - Private detached house - Perfect location praised in reviews - Renovated, modern & clean - Screened-in porch for your enjoyment - Stay longer: stocked kitchen, washer/dryer, TV - One dedicated parking spot Permit Number: 06043