Holiday rentals with outdoor seating in Charleston

Charming 2 Bdrm/3 bath Cottage by Marion Square

Wake up refreshed in the carved four-poster and curl up on the tan leather couch under the skylights in this charming brick house built in 1802. Gather for a leisurely breakfast in the morning, or cocktails in the afternoon in the illuminated, landscaped courtyard. #BL005522012017 Not recommended for children. This entire home was renovated in 2017. This charming cottage has sleeping for six. The first floor has a queen sleeper sofa in the living room plus a full bath off of the living room. The second floor has two bedrooms - one king bed with private bath and one queen bed with private bath. The bedrooms and the living room have new flat screen TVs. Hardwood flooring and tile throughout. New stainless steel appliances and granite counter tops in the kitchen. Linens are Eqyptian cotton and the towels are plush! The guest cottage is very comfortable and clean! There is a private lighted, landscaped courtyard with a table and chairs and a Charleston bench. Guests have access to the entire house and a private, landscaped and lighted courtyard with table and chairs. There is on-site parking for 2 cars. I do not live on the property, but am available if needed. The property is around 300 feet from King Street, the major shopping and dining center in the heart of downtown Charleston. The property is located near the intersection of King and Calhoun Streets. Marion Square, Gaillard Center, and other activities are within easy reach. This location is in the center of the downtown activity with great access to shops and restaurants on foot. DASH is a free shuttle service for the Historic Peninsula area of the City of Charleston. One of the trolley stops is 1/2 block away.

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

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, have a cocktail on the balcony, or just sit and watch the sun set from the roof top deck. 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.

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 4 bikes included. Come and enjoy this beautiful property!

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

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.

The Most Charming Old Brick Alley, Charleston

This gorgeous house at the end of a quiet cobblestone alley is just one block away from upper King Street, the epicenter of the city's renowned restaurant and nightlife district. This home comes with ONE off-street parking space. Enjoy some of Charleston's best local dining all within one block of this home! Come experience Charleston's southern hospitality while staying in a traditional Charleston home. Please note this unit is handicap inaccessible.

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

Fire Tower Downtown Gem 1BR with Balcony & Views!

Stay in style at Fire Tower, a 2023-built condo just off King Street. This 1BR/1BA retreat features a plush king bed with en-suite, full kitchen, Smart TV, and private balcony. Enjoy modern amenities including WiFi, and off-street parking. Relax on the shared rooftop with skyline views or unwind in the courtyard and terrace. Perfectly located to explore Charleston’s dining, shops, and history.