Holiday rentals with outdoor seating in Charleston

The James: “Tiny” Home b/w Downtown & Folly

The James is a unique NEW 530 sq ft retro coastal tiny home located in a gorgeous neighborhood on James Island ◡̈ 10 mins to downtown Charleston 12 minutes to Folly Beach Walking distance to restaurants The James sleeps up to 6 people and 2 dogs (NO PET FEE) & boasts a private fenced yard & patio with an outdoor shower and Clawfoot tub! The James is ideal for solo travelers, couples, families, those traveling w/ their dog(s), those w/ limited mobility and groups of friends. #BNB-2023-02

Walk to restaurants! New, beautiful & clean home

Welcome to Curlew Corner! A new, private upstairs guesthouse in one of Charleston’s most desirable neighborhoods. With a king bed+sofa bed, this is an ideal spot for couples, friends, or small families looking for a getaway in a beautiful city! Location! The guesthouse is within walking distance to many eateries, bars, a music venue, cinema, farmer’s market, yoga studio, playground, boat landing, and beautiful water views. Close to downtown Charleston and Folly Beach, you can’t beat this spot!

The Little Pink House

Nestled under the grand live oaks of Bogard Street, The Little Pink House is a picturesque Charleston carriage house. This thoughtfully crafted guest house invites couples and individuals alike to experience the best of Charleston in a private, yet centrally located retreat. ♥ Elegantly styled & warmly decorated ♥ Traditional southern porches ♥ A short 4 blocks to King Street ♥ Neighborhood gems just steps away Beloved by many - newlyweds, honeymooners, couples - seeking a unique getaway!

3 Bdrm Home w Courtyard & parking- Heart of City

Welcome to our historic home Est. 1802! This charming home was renovated in 2017 & is located in the heart of downtown Charleston, near the intersection of King & Calhoun St. It is steps away from King St...the center of shopping, great restaurants, Marion Square & other downtown activities! Fully licensed & permitted by the City of Charleston BL005521012017 Offered separately is an adjacent property, the Guest House (2 Bdrm + Queen Sleeper + 3.5 bath) www.airbnb.com/rooms/17119598

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!

Endless Summer Downtown CHS

This historic property was built in 1838 with original porches to this grand Charleston home. Full renovation in January 2023 to create the beachy, coastal, surf chic spot it is today. Updates include new kitchen, two new bathrooms & fresh paint. Relax surrounded by a fun vibe and great local art. Downtown dining and bars are a short stroll away but we are still tucked in the quiet neighborhood close to MUSC Hospital. Walkable to Upper King Street nightlife and dining.

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# OP2025-06925

Historic District | Private Luxury Retreat

Experience timeless Charleston elegance in this historic residence. High ceilings, wood floors, and oversized sash windows create a graceful retreat. Set in Charleston’s Historic District near the French Quarter, King Street, Colonial Lake, and The Battery—peaceful at night yet walkable to top destinations. Private entrance, 1,000 sq. ft. of curated living space, plus dedicated private off-street parking directly at the home—a rare downtown luxury. (OP2025-06356)

The Parlor | 1BD w/ Huge Porch, King Bed + Parking

Unwind and enjoy generous space in this historic retreat. A large private piazza overlooking the backyard offers the feeling of having your very own Charleston dream home. Built circa 1850 and converted to apartments over a century ago, this farmhouse features expansive rooms with original moldings, mantels, and hardwood floors. A thoughtful restoration blends modern conveniences, like an updated kitchen and bath, with the timeless charm that defines Charleston.

Stunning Couples Cottage with Creek Dock!

You will fall in love with this stunning, newly-built guest cottage nestled under the canopy of a majestic 400-year-old live oak tree! Providing ultimate comfort, convenience and serenity, this is the perfect place to launch your Charleston adventure – 10 minutes to Shem Creek, & 15 minutes to Sullivan's Island or Downtown Charleston. PLUS, come enjoy our brand new dock on the creek! A picture-perfect spot to relax and enjoy the stunning Lowcountry scenery!

Silverlight Cottage in Park Circle

A spacious retreat (780 sq ft.) in Park Circle: Elegant, gracious + charming. Brand new custom built guest house designed with a nod to classic Charleston architectural influence: open concept indoor - outdoor space to large shady screened porch where a perpetual breeze from the not-too-distant coastline blows gently all year round. Visitors will return from their travel deeply restored and revived - having experienced well-appointed accommodation.

2500SF Downtown 1849 home w/ pool!

The perfect Oasis in the middle of the Peninsula... Come home to this 2,500 SF c.1849 historic property and take a dip in the pool after a long day walking around or relax and have a cocktail on the balcony. Walk out the door and explore Cannonborough-Elliotborough and some of the best restaurants the City has to offer. Off-street parking for 1-2 vehicles is provided, a rarity downtown. We are a legal City licensed short-term rental 2026 OP. 07096.