Family-friendly holiday rentals 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

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

Oceanfront Sea Cabin 226 B - Discover Charleston!

Positioned right in the heart of 🌴 Isle of Palms 🌴 this charming 2nd floor condo is just steps from a private pier and sandy shore, with shopping, dining and entertainment close by. Enjoy a panoramic view of the Atlantic Ocean from a private balcony overlooking a community pool and beautiful natural dunes. Unwind and relax with breathtaking sunrises that paint the sky. 👉 Located just off the IOP Connector, making a trip to nearby Mount Pleasant or Downtown Charleston is easy and stress free!

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

Location! Hip Downtown KING at Cannon, Park 2 cars

Incredible LOCATION! Fresh 2 bdrm apt - with brand new bathroom - located in historic downtown duplex 75 feet from KING St! Smartly appointed, the unit is business traveler ready with SUPER speedy WI-FI and FREE Off Street PARKING for 2 cars. Stay within 1 minute walk of Charleston's best bars, nightlife & restaurants HOT Upper King St area. Sound proofing window inserts for a cozy buffer to your downtown experience - if you are a light sleeper this location may not be for you. OP2018-00378.

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!

Four Oaks Cottage at Park Circle

Experience Charleston’s hippest neighborhood in a recently renovated midcentury cottage. Walk steps to Park Circle's award-winning restaurants, or hop a 15-minute ride to downtown Charleston. Relax on the yard's tree swing after your Sullivan's Island beach day, then star gaze under hundred-year-old Lowcountry oaks. Stroll to nearby bars, breweries, distilleries, and shops in this historic, convenient, friendly, and local Charleston community. Short-Term Rental Permit 2026-0129

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

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!

Old Village Guesthouse walkable, close to beach/DT

Location. Location. Location! It's trite, but it's true. You’ll be minutes from downtown Charleston and the beach at Sullivan’s Island when you stay with us in the historic Old Village of Mount Pleasant. Walk to some of the town’s best restaurants and waterfront bars or seize the moment to relax in our breezy, modern guest house in one of the oldest, most beautiful neighborhoods in the country. STR permit number: ST260274 Business license number: 24-026855

Historic Charleston Charm | Private Luxe Retreat

Experience timeless Charleston elegance in this historic residence. High ceilings, polished wood floors, and oversized sash windows create a graceful escape. Set in Charleston’s Historic District adjoining the French Quarter, near 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 free dedicated off-street parking. (OP2025-06356)

Hot Tub Hideaway • Parking • 1 Block to King St!

✨ Welcome to The Palms of Charleston – Suite C! 🌴 ☀️ Large Courtyard with Hot Tub 📍 1 Block to King St – Walk to Charleston’s Best Dining, Shopping & Nightlife 🌿 Balcony with Seating 🚙 Off-Site Parking for 1 Vehicle 🛏️ Comfortable Mattresses 📺 Smart TV – Streaming Included 🛜 High-Speed WiFi + Desk 🫧 Washer/Dryer 🍳 Fully Stocked Kitchen ☕️ Local Coffee + Supplies 🚿 Hair Tools Provided 🎶 Record Player + Game Console