Holiday rentals with outdoor seating in Charleston

Bikes + Parking for free! Guesthouse Downtown

New & clean w/modern amenities, our “Lil’ Blue 💙 Bungalow” is ready to greet you! Complete with Washer & Dryer, Kitchen, Free Parking, 2 Bikes… you can't beat what this location has to offer! 2 blocks to grocery & pharmacy on upper King St plus you’re right around the corner from hip, award-winning coffee shops, restaurants & trendy bars. Get ready to take on Charleston & then recharge at the end of your day at your private, central Downtown Retreat! Perfect for couples & traveling professionals

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

Historic Vintage Charm | Private Modern Luxe

Turn back time in this refined historic Charleston residence (OP2025-06356). Soaring 12-ft ceilings, polished wood floors, and grand sash windows set the tone for an elegant retreat. A master bedroom and curtained sunroom each offer king beds for flexible sleeping. Located in a quiet, walkable historic downtown neighborhood. Perfect for couples or a sophisticated girls’ weekend. Private entrance, thoughtfully designed 1,000 sq. ft. interior. Exclusive off-street parking with EV charger.

Waterfront home w/ Deepwater dock on Stono River!

3bd/2bath waterfront home with deep water dock on the Stono River on Johns Island! Beautiful lot in quiet neighborhood, with large majestic live oaks. Enjoy beautiful views of the Stono River from the sunroom or patio, ideal for catching pretty sunsets! Great fishing and crabbing right off dock as well as boating, kayaking, or swimming. Bring your own boat to keep at dock! Located across from public boat landing! 2 kayaks, crab pot and 2 bikes included. Come and enjoy this beautiful property!

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

Waterfront Treehouse

Marsh and creekside Luxury Treehouse nestled among historic Grand Oaks. Private Elevated TreeHouse that has closeup views of trees and wildlife from every oversized window. Sit back and relax on the large deck watching the ebb and flow of the tide as fish jump, birds hunt and fiddler crabs defend their bank. (This property has been granted an exemption and does not accept pets or Service animals due to allergies.)

Stylish Loft Historic Downtown Charleston Condo

This renovated condo is the place you want to stay on your next trip to Charleston. Weekend getaway, bridge run, Spoleto, Spring/Fall house tours or even a staycation! One bedroom loft style condo with spacious living, dining, kitchen and half bath located downstairs. Relax in this quiet corner unit! Step outside and the city is at your feet! Check out our sister property! https://www.airbnb.com/rooms/20436304

Wilden House | Luxury, Regal, Spacious

A stay fit for royalty. Built circa 1887, The Wilden House was meticulously restored in 2020, blending historic charm with modern comfort. Enjoy soaring 11’ ceilings, original chandeliers, crown molding, and stained glass. This 1,300+ sq. ft. first-floor unit features a large front porch, on-site parking, and a prime location steps from cafés, restaurants, and the vibrant shops of Charleston’s Upper King Street.

Private waterfront apt in the oaks

Romantic get away for nature lovers. Private 2nd floor studio apartment over garage (guest parking), nestled among large live oaks overlooking tidal creek & dock on wooded property. Less than 30 minutes from downtown Charleston, Folly Beach, Kiawah. Shrimp, fish, crab or just enjoy the hammock on the dock. Or go for a paddle in one of the kayaks provided for a small fee.