Holiday rentals in Drum Island

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

Pleasant Place New Build + Pool Great for Families

Bring your family & enjoy our brand new 2020 built home minutes to downtown Charleston, only 6 miles from the beach! Pleasant Place is in the BEST location to top restaurants & activities. This lovely 2700sqft 4 BR 3 BA pleasantly sleeps 10 guests and has all the familiar comforts of home with a fenced-in pool oasis, on a quiet street within walking distance to the Ravenel bridge connecting you to the heart of Charleston. Just a few minutes drive to the best beaches. Bring the family, book now!

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!

Bridgerton inspired fantasy 2 min from park circle

Live out your Bridgerton fantasy in this stunning historic space. The apartment features antique furnishings/art, a private entrance and patio with lounge and a hot tub (The hot tub is available Apr through Nov). Off street parking. A sumptuous bathroom with an oversized soaking tub and a kitchenette. There is also a 55 inch frame tv in the bedroom including WiFi. Available for photo shoots upon request rates may differ please contact host prior. Bridal pics by Olivia Allain Permit#2026-0414

Historical Southern Charmer with Gated Parking

Two blocks off King Street, Cayo Cañón is located in Charleston’s charming historic Cannonborough-Elliottborough (C-E) neighborhood. A traditional (1835) Charleston home, our listing features the home’s entire first floor (1100 sqft), one king bed, one sofa bed, a breakfast nook, deck, gated off street parking, and plenty of outdoor space. When staying at Cayo Cañón, you’ll find yourself steps away from the Holy City’s highest rated restaurants, bars, historical sites, parks, and shopping.

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.

Upscale EARL CRT 3-bdrm Old Village/Shem Creek

STR PERMIT #ST250176 BUSINESS LICENSE #20135982 3-bdrm Earl's Court neoclassical upscale home, nestled in the heart of the historic Old Village, offering the charm of low country living. Just a block from Shem Creek bars & restaurants, Old Village shops & eateries, Alhambra Hall, Pitt St Bridge, and a weekly all food Farmer's market, featuring low countries finest! The Arthur Ravenel Bridge, downtown Charleston, Sullivan's Island & IOP beaches are all bike riding distance.

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

Daniel Island Getaway

Welcome to your home away from home near Center Park on Daniel Island, located within 20 minutes from Downtown Charleston, Sullivan’s Island and Isle of Palms. This almost 600sqft above garage guest house has a separate bedroom and full bathroom in addition to a spacious living room with a Queen sofa bed and a kitchen area that will meet all of your basic needs. The kitchen includes a Keurig, microwave and griddle. There is even an outdoor shower for guests to use.

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!