Charleston, SC 5+ Bedroom Vacation Rentals

Welcome to The Penny Palace: Where History Meets Modern Comfort!This 3-story historic gem, is located in the heart of the Historical District in downtown Charleston and invites you to experience the timeless appeal of the 1800s with all the...

Summary:✨ Welcome to Azaleas on Spring! ???????? 2 Blocks to King St! Walk to Charleston’s Finest Dining, Shopping & Nightlife???? Ideal for Giant Groups – Families, Wedding Guests, Bachelor(ettes) & Work Retreats???? Multiple Outdoor Spaces...

3,000 Sq Ft | Family-Friendly Conveniences | 3 Mi to Folly BeachMake this 5-bedroom, 3-bathroom vacation rental your home base as you discover all Charleston has to offer. The 'James Island Folly Family Retreat' includes multiple living areas, ideal...

Welcome to life in the Lowcountry at The Lookout! The design of this home embodies the natural beauty of life on the water with comfort and style. Heated pool just installed! Great place to cool off year round- close to the outdoor TV...

Summary:OP2025-05861Point of View Cottage is a bright and airy Casa Zoë getaway made from two seamlessly connected spaces - ideal for families, friends, or groups who want to stay together but still appreciate a bit of breathing room. With five...

Encompass yourself in the history of Charleston by staying in this freshly refreshed 1890`s single home. This entire two story home offers guests all the aesthetic features of a Charleston Single House from its sizable double piazzas with blue...

Sleeps up to 16! This modern, newly remodeled home consists of 2 enormous apartments, rentable separately or together. You have a private backyard to relax/dine with a wide umbrella. Wood floors sit beneath exposed beams, w/ stainless steel...

Summary:Discover luxury pair of completely refreshed luxury homes ideal for a huge group, located next door to each other just moments from King St. Indulge in beautiful interiors awash with natural light from wrap-around windows. These Charleston...

Summary:Discover Blue Magnolia, your beautiful and cavernous Charleston getaway. This 7BR/4BA home combines classic Southern appeal with modern comfort, making it ideal for families or groups. Unwind on the inviting front porch, soak in the airy...

Summary:Draped in Spanish moss and located within a beautiful Charleston neighborhood, this newly modernized grandiose 10-bedroom, 7-bath getaway blends timeless Southern character with modern luxury. Freshly remodeled in September 2025, this...

Summary:Stay at The Dunes on Spring, our gorgeously modernized 1905 Charleston Victorian duplex home in the heart of Cannonborough. Just 2 blocks from King Street, this striking property features nearly 2600 square feet of ideally designed space...

Summary:Welcome to The OakTree, your boho-chic haven in the heart of downtown Charleston, where artistic flair meets generous space. Ideal for huge groups, families, or creative retreats, this 7-bedroom home offers character, comfort, and close...

Summary:Discover this massive 10-bedroom, 10-bathroom getaway in downtown Charleston, accommodating up to 22 guests. Luxuriate in open living spaces, a entirely equipped kitchen, and king-size beds throughout. With off-street parking, modern...

The property located at 93.5 unit A & B The Manor is a gorgeous two-story new construction home providing all the amenities of home combined with fresh furnishings and an extraordinary location.Unit A is the first-floor unit with an open concept...

Welcome to the Holy City, and the historic southern appeal of the Charleston peninsula. Our Vacation Rental By Owner is located in handsome downtown Charleston and just mins. away from MUSC, the College of Charleston, and King Street’s shopping...

Summary:Step into this handsomely preserved Charleston-style home where old-world appeal meets modern comfort. Ideal for couples, families, or modest groups, it offers a welcoming getaway filled with character in a prime location. Located in a...

Summary:Discover 'Palmetto on Spring | Rooftop Suite,' a impressive 5-bed, 5.5-bath Charleston getaway. This modernized home spans three floors, featuring a detached guesthouse and a private rooftop terrace with city vistas. Ideal for huge groups...

Summary:Welcome to Magnolia House, a grandiose 6 bedroom, 3 bathroom two-story Charleston style home that blends timeless character with comfortable, modern touches. Ideal for families or groups seeking space, beauty, and convenience in one place...