Holiday rentals with outdoor seating 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

Charleston Harbor view, garage apt

Spacious apartment with high ceilings. The back porch has a fantastic view of Charleston harbor. The house is located in a quiet neighborhood, very close to downtown and also to beaches. Private dock, kayaks, bicycles (not fancy) and the possibility, weather and tides permitting, of a motorboat ride around the harbor. It is incredibly peaceful here; like being in the country, but it's in the middle of the city. Mt Pleasant Short Term Rental License #STR240286, MP Business License # 20122588

★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*

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!

Petite Maison- guesthouse, Downtown Charleston

Take it easy at this unique and tranquil getaway located in the quiet and trendy downtown neighborhood of Wagener Terrace. Newly renovated, this stylish guest house is just 2 miles from the center of historic Charleston. Petite Maison is the perfect stay for couples or singles looking to live like a local in this popular downtown neighborhood. Enjoy a quiet walk or bike ride to Hampton Park and some of the best restaurants and bars in the city. Residental STR Permit # OP2023-04086

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

James Island "La Casita" Nestled btw Beach & City

Wake up to the 2 grand oaks just outside your window. Visit Folly Beach (14 minutes) or Historic Downtown Charleston (9 minutes). Craft your own meal in the complete kitchen or try one of the many renowned Charleston restaurants recognized by foodies worldwide. Visit James Island County Park & Waterpark (1 mile). Take a trip to the local Farmer's Market or the Municipal Golf Club. Then stroll down the (Woodland Shores) road for a spectacular view of the wetlands.

Marsh view retreat near Folly Beach and Downtown

**Please review additional notes below about potential construction noise** Welcome to Lighthouse Lookout, a private-entry guest suite, offering a truly unique Charleston experience. Conveniently located on James Island, between Folly Beach and Downtown Charleston. The private balcony provides stunning views of the salt marsh and historic Morris Island Lighthouse. It’s the perfect place to relax and enjoy the changing tides, abundant wildlife, and scenic sunrises.