Holiday rentals in Dewees Island

★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*

The James: “Tiny” Home b/w Downtown & Folly

The James is a unique 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

Architecture* La Cabaña * Beach 8 min * 2 Bdrm

Nestled on an old dirt road sits La Cabaña, a uniquely designed haven of relaxation and a vibrant tropical scene. This exquisite property has 2 master suites, thoughtfully positioned at opposite ends of the house to offer privacy and tranquility for couples seeking a rejuvenating getaway. Wake up to the sounds of a bubbly lagoon and a hot cup of coffee in your private retreat. La Cabaña's location offers easy access to the IOP Beach & a short drive to CHS culinary scene. ZSTR-12-25-01315

Private Rifle Range Cottage -Near IOP & Charleston

Welcome to The Rifle Range Cottage! a spacious 2BR/1BA Mount Pleasant escape on a rare 1+ acre lot, just north of the IOP Connector. Minutes from Shem Creek, 5 minutes to Sullivan's Island & IOP beaches, and 7 minutes to historic downtown Charleston. Sleeping 4 guests with hardwood floors, stylish living spaces, smart TVs throughout, and a fenced in Side yard with outdoor shower and Grill. The perfect Low country base for families, weddings, and unforgettable Charleston getaways!

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.

Bungalow Under The Oaks

Small guest house in the heart of Mount Pleasant! Ideally located to both Isle of Palms and Sullivan's Island beaches (both 7 minutes) and only 15 minutes to the heart of historic downtown Charleston. Our private guest bungalow is a perfect launching spot for all your exploring. End the day relaxing under the shade of our mature live oak. The house has its own entrance and separate yard that is fully fenced in. LHR Permit: ZSTR-02-21-00318, License: LIC-3-21-252314.

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 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

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.

Casa Zoë | Historic Garden Carriage House CHS

OP2026-07206 A hidden gem in the heart of Charleston, Gibbon House is a beautifully restored brick carriage house with a story to tell. Once the office space for the Charleston Symphony Orchestra, it now offers elegant, design-forward hospitality just steps from King Street. Featured in Condé Nast Traveler, Gibbon House combines history, charm, and comfort with Casa Zoë’s signature warmth and character.

Pet Friendly&Fenced Yard Near Beaches & Downtown!

Imagine starting your vacation knowing that everything that you might need awaits you. After a day of sun and fun at Isle of Palms beach, or of exploring all of the activity that downtown Charleston has to offer, enjoy the peaceful serenity of your very own private backyard oasis. This is the experience that we strive to create for all of our guests - this, is purposeful travel.