Holiday rentals in Dewees Island

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

Clean Coastal Cottage 5mi to Isle of Palms Beach

Sunny Side Up is a freshly updated coastal beach house, featuring 4BR/2BA, perfectly located minutes from the areas best beaches, shopping, dining and nightlife. You'll be 3 miles from Isle of Palms, 10 minutes from Sullivan's Island, and only 20 minutes from downtown Charleston. Spend the day enjoying the shared pool or exploring the area and return home to your private screened-in porch overlooking a spacious backyard with hammock, fire pit and chicken coop. #ST260150 S.C. BL-24-026814

Marshfront Villa In The Trees - Near Beach & Bay

"The most unique and relaxing place to enjoy the tranquility and experience of Edisto. We did not want to leave" - Sambo Nestled atop 360-degree marsh views, you'll be immersed in the exotic natural beauty and wildlife of the Edisto sea island. Hear the waves crashing at the beach from the front porch and watch the marsh tides rise and fall from your choice of the many porches. "Nature with luxury.. our group loved floating from the house out to the inlet for private beach days" - JP

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!

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

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!

Mt Pleasant Cottage-Downtown, Shem Creek & Beaches

Make the most of your visit to Charleston by staying at this fully renovated cottage in the heart of Mount Pleasant! This property offers an open floor plan, deck area, and spacious backyard. Conveniently located just minutes away from Shem Creek, Downtown Charleston, Isle of Palms, Sullivans Island, and a variety of restaurants/shopping! -12 mins to Isle of Palms -13 mins to Sullivans Island -12 mins to Shem Creek -14 mins to Downtown

Ruby's Cottage/Brand New Close to Beach & Downtown

Be one of the first to enjoy this beautiful, newly built detached guest house with private entrance, keyless entry, and separate gated yard with private patio. Located in a quiet neighborhood just minutes from fine dining, shopping and only 10 miles from Isle of Palms and Sullivan’s Island beaches. Grocery stores, restaurants, historic sites, golf courses, hiking trails, downtown Charleston and more are just minutes away.