Vacation rentals in Dewees Island

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*

Stono River Retreat - Waterfront.

New cozy wood cabin tastefully decorated, situated among the live oak trees on the Stono River (ICW). Cabin is convenient to downtown Charleston, the white sand beaches of Kiawah Island and Folly Beach. Enjoy nearby sights and fabulous local food. End your day relaxing on the screened porch and deck overlooking the serene Stono River & the sunsets! Enjoy the water by launching your kayak or boat on the Stono River at the Limehouse boat landing, just 2 miles away. Abundant wildlife viewing!

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

Kate's Place: An ideal retreat on the coast

Welcome to Kate's Place, a cozy and extra clean vacation getaway in Mt. Pleasant. Many guests have described Kate's Place as an ideal retreat, given its close proximity to beaches (one mile away) and restaurants. Downtown Charleston is a ten-minute drive. This apartment has an exterior door with no shared indoor space. A private parking spot to boot! You'll love Kate's Place! Perfect for two! Do check out all the 5-STAR reviews! TOMP Permit Number - ST260355 TOMP BL# - 20132913

Mount Pleasant oasis near beach with private pool!

Beautifully updated Mount Pleasant home with a pool! The home's perfectly located just a few short miles from the IOP beaches and a stone's throw from great shopping nearby. This house is the perfect spot for a family vacation or just a weekend away with friends as it offers 3 bedrooms (2 with queen beds and 1 with a king bed). You can enjoy a day at the beach (5 mins away), just relax by the pool, or swim laps in the endless pool system with a push of a button. LIC# ST260331 Bus# 20139685

Entire Cottage! central to beach & downtown

ST250127 BL24011126 Enjoy your Charleston stay in this 2bd/2bath, stylish cottage set in a fabulous location! Enter your own private entrance overlooking a beautiful garden with shared backyard yet privately partitioned. Walking distance from a few restaurants, ice cream shop, pharmacy and grocery stores. Nestled in a quiet neighborhood between Sullivans Island beach and historic downtown. Head to the nearby Charleston Harbor and Shem Creek boardwalk for gorgeous views and amazing sunsets!

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!

Coziest Townhome in the heart of Mt. Pleasant

Pleasant Places is conveniently located to the beaches, Shem Creek’s popular restaurants and tourist attractions and is minutes from Historical downtown Charleston. Drive, walk or bike to many local attractions and restaurants. 20 min from Charleston Airport 10 min from Sullivan's Island and Isle of Palms 8 min to Downtown Charleston 5 min to Shem Creek Bars & Restaurants 5 min to grocery stores - Whole Foods and Trader Joes ST260067 MP BL-24-016987

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.

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.