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

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!

★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*

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.

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

Heart of Park Circle| Peaceful & Private | Firepit

Enjoy a stylish and peaceful stay at this centrally-located, Park Circle cottage. Set back from the street for added privacy, with a beautiful front porch and backyard. Just a 5 min walk to the lively restaurants of Park Circle and a short 20 min drive to Historic Downtown Charleston & nearby beaches. Filled with an abundance of natural light, featuring two bedrooms, one bath & a sunroom with a daybed. Fully equipped with all you need for a comfortable stay in the Park Circle neighborhood!

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!

Shem Creek Cottage!

Your own newly renovated cottage in a phenomenal location! Walk or ride bikes to Shem Creek and hundreds of restaurants and bars. 3 minute drive or 10 minute bike ride to downtown Charleston. Private neighborhood path through the marsh to Shem Creek and Shrimpboats. Cottage equipped with king bed, pullout king bed couch, full kitchen, bath, two large TV’s, washer & dryer, counter with barstools and private patio. 50 paces to neighborhood park! Permit #ST260119 - License #20121152

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

Private Pool Oasis • Walk to Folly Beach

Luxuriate in the lagoon pool or large hot tub and listen to the ocean on this private dune. You CAN have it all: an intimate, luxurious, artsy, home on a hill above the Folly nightlife... 3 master bedrms/2 baths!) AND... ONLY 2 BLOCKS to Folly's center AND the beach.Unforgettable PORCH times! It's MASSIVE! ********One of the king beds/baths is an attached guest house. ***** Enjoy the sounds of the pool fountain and the walks to the pubs/restaurants!

•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)