Holiday rentals in Charleston

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!

Downtown Cheerful, 3 BDRM + 3 Full Bath +GOLF CART

Truly the absolute BEST place to be if you love great food. ★ Walk Score 96 ★ 5 min walk to King Street ★ Safe & Lively neighborhood ★ Washer + Dryer in unit ★ Free secured parking for 2 vehicles ★ 6 person GOLF CART on property available for rent Elliotborough is not only a local favorite but it is a mecca for foodies. You will be surrounded by top restaurants; Vern's, Leons, Chubby Fish, Southbound, Kultura, Chez Nous, Melfi's, The Ordinary, Babas, Prohibition.....so MANY walk-able places!

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!

1BR cottage~Charleston Peninsula~20min to beach

Welcome to The D'alhana~a mix of cottage and studio. Our property is considered a "back house" having all the fixins. Newly updated and situated in a National Register district, this place is exactly what Charleston is all about. 📍Short drive to historic downtown CHS 🏖️ Beaches: 8.6 miles to Sullivan's, 11.2 to Folly, 14.1 to IOP 🛏️ Queen bed 🚿 Full bathroom w/ custom walk-in shower 📺 Smart TV in living room 🍽️ Fully functional kitchen 🧺 Washer/dryer 🚗1 dedicated parking spot

Historic Downtown Farmhouse

Visit Charleston in our Pre-Civil War Single House, an architecture unique to Charleston! Originally Nunan Strawberry Farm. Sip tea on our traditional side porch with haint blue ceilings while listening to the cicadas and watching Carolina Chickadees. Enjoy the historic houses in the neighborhood and stroll or Uber to the Charleston Battery or City Market. You're welcome to spend the holidays with us but please do not check-in on the day of. Thank you! CHS STR: OP2023-03634

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

Bridgerton inspired fantasy 2 min from park circle

Fully restored italian influenced cottage in Charleston. Live out your Bridgerton fantasy in this stunning suite. It’s a standalone apartment done to highest level. Apartment featuring a private entrance and patio with lounge and a hot tub that is available April through November. 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. N-Chas Permit#2024-0556

•The Nina House• 3 Miles to Downtown Charleston

Discover the Nina House, a chic bohemian retreat minutes from historic Charleston. Enjoy the best of both worlds: vibrant city life close by, yet tucked into a quiet neighborhood, free from noise and parking hassles. Relax in sunlight, eclectic interiors or unwind in the private outdoor clawfoot tub. With style, comfort, and convenience in equal measure, The Nina House is your peaceful escape with Charleston‘s charm at your doorstep. (OP2023-04138)

Oak House: Downtown Peninsular, Historic, Serene!

Experience the charming life of downtown Charleston and relax in this sunlit home from 1915. You will sleep in the most comfortable beds, enjoy luxurious bathrooms and a full kitchen. Bond over games like cone hole and more! Restaurants (Lillian’s!), bars, the Citadel, sports stadium and corner stores are in walking distance. Located in the middle of the downtown Charleston peninsular underneath the iconic live oak trees and next to Hampton Park.

Guesthouse Convenient to Charleston, Shem Creek, and Beaches

Relax in this separate guest home nestled in a well-established Lowcountry neighborhood. The ‘treehouse’ has an open-plan design with vaulted notched board ceilings, creating a feeling of light and space, with elegant furnishings throughout. The well-equipped kitchen and grill on the porch encourages intimate home cooking. We lived in this space before we moved into the main house, so we can attest to it being comfortable, and well maintained.