Charleston, SC 5+ Bedroom Vacation Rentals

Feel the timeless appeal of Charleston’s historic peninsula, the Holy City. Stay just mins. from MUSC, the College of Charleston, and the vibrant shopping, dining, and nightlife of King Street. From this ideally located downtown home, you’ll be...

This listing is combined of two traditional style Charleston row homes with great outdoor space. The two homes are directly beside each other and have their own separate entrances. Each home has plenty of space to all gather together may it be...

Summary:As part of the esteemed collection, The Heirloom, this striking 18-bedroom compound is located on Spring Street in the heart of Charleston. Ideal for huge groups, this completely refreshed property combines two handsome Victorian homes with...

As featured in Vogue.Named as Charleston’s most design-forward Airbnb.Suitably located in the heart of Downtown Charleston, it is our honor to introduce The Juliette. Prioritizing an opulent aesthetic with comfort in mind, it is here that you'll...

Permit Number: 06052The Space: Two full apartments. Six bedrooms. Four baths. One seamless stay.This entirely remodeled three-story Charleston home is ideal for enormous groups who want space to spread out without sacrificing style. Bright...

Summary:Welcome to The Charlee on Cannon, an elevated getaway in the heart of downtown Charleston. This handsomely designed five-bedroom residence features broad living spaces, a chef-inspired kitchen, and a private rooftop terrace ideal for...

Summary:Recently refreshed with two full kitchens and modren decor, this home comfortably accommodates your entire event. Located in the heart of the city, the Heirloom on Spring extravagant getaway blends historic character with modern comfort...

Welcome to the Mint Julep Residence, the grandest home in the Smalls Alley collection of standalone luxury homes in downtown Charleston. Unlike its sister residences in the alley, this famed historic home sits at its own address, 129 Cannon Street...

Summary:Welcome to Cannon Collective, a roomy 5 bedroom home in downtown Charleston full of character, elegance and prime access. Ideal for sizable groups, families or gatherings looking for comfort, appeal and space. You will find yourself walking...

Summary:Welcome to The Palms of Charleston!☀️ Cavernous Private Courtyard + Hot Tub???? 1 Block to King St! Walk to Charleston’s Finest Dining, Shopping & Nightlife???? Ideal for Substantial Groups – Families, Weddings, & Work Retreats???...

Completed in February 2025, The Soiree is a fresh take on the Charleston experience, revitalizing Charleston’s appeal with modern elegance. While we deeply savor the historic structures that define the city, The Soiree offers a new kind of luxury...

East 42 A & B is the combined listing for the two homes below. These two handsome homes can be connected via the fire door in the hallway creating a alluring five bedroom, five bathroom, with a queen murphy bed for flex linens, and two private...

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

Summary:Welcome to your Charleston escape, a generously sized 6-bedroom home constructed for big groups who want to be in the heart of the action yet savor broad living spaces. Ideal for family get-togethers or friend get-togethers, this home offers...

82 A & B is a cavernous two-story home, charmingly located within walking distance of Charleston's best eateries, bars, and attractions. Ideal for huge groups, the home features two completely equipped kitchens, two living areas, and multiple...

Summary:Welcome to The Grandiose Estate, a private getaway in the heart of downtown Charleston, SC. Located within a meticulously restored historic home, this exclusive property features four entirely furnished residences, creating the ideal setting...

3,000 Sq Ft | Family-Friendly Conveniences | 3 Mi to Folly Beach | 10 Mi to DtwnMake 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...

Permit Number: OP2026-07350The Space: Welcome to The Poseidon — a cavernous downtown getaway just off Spring Street. With 5 bedrooms, 3.5 baths, and an open layout constructed for gathering, it’s an ideal setup for families and bigger...