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Charleston, SC 5+ Bedroom Vacation Rentals

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163 rentals found
The Chapel | Grand 8BR Charmer - Walkabl...

Summary:Welcome to The Chapel, a handsomely restored 8-bedroom gem in Charleston where character, comfort and convenience come together. Ideal for huge families or groups, this home offers cavernous common areas, fashonable design details and a...

  • Charleston
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 16
100ft to King St. Outdoor Space, Modern ...

Summary:Welcome to your Charleston gathering spot, a roomy 6-bedroom home constructed for sizable groups seeking style, flexibility, and unbeatable walkability. Featuring two high end kitchens, generous living spaces, and just one block from King...

  • Charleston
  • 6 Bedrooms
  • 5 Bathrooms
  • Sleeps 16
Guesthouse Charleston: SOUTH (82 A & B)

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

  • Charleston
  • 8 Bedrooms
  • 9 Bathrooms
  • Sleeps 18
Grand 10BR Charleston Home with Speakeas...

Summary:Draped in Spanish moss and located within a striking Charleston neighborhood, Heirloom on Cannon is a huge 10-bedroom, 7-bath getaway blends timeless Southern character with modern luxury. Freshly refreshed in September 2025, this historic...

  • Charleston
  • 10 Bedrooms
  • 7 Bathrooms
  • Sleeps 26
Luxury 8BR/6.5BA Downtown w Outdoor Spac...

Summary:Bring everybody together in this cavernous 8BR/6.5BA Charleston home featuring two kitchens, dual living areas, and chic design throughout. Just 4 blocks from King Street, this getaway offers modern amenities with historic appeal, high-speed...

  • Charleston
  • 8 Bedrooms
  • 6 Bathrooms
  • Sleeps 18
Hot Tub • Rooftop • Parking • Walk...

Summary:Welcome to Camellias on Cannon!☀️ Private Rooftop + Courtyard & Hot Tub???? 3 Blocks to King St – Walk to Charleston’s Finest Dining, Shopping & Nightlife???? Ideal for Sizable Groups – Families, Weddings, & Work Retreats???...

  • Charleston
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
St. Philip Collection - Pair of newly re...

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...

  • Charleston
  • 5 Bedrooms
  • 6 Bathrooms
  • Sleeps 14
Cozy low country get away with water vie...

Roomy home with sizable front and back yard surrounded by naturalistic beauty of low country scenery. Appreciate water view from front deck or sunsets and wild roaming turkeys and deer on covered back deck. Charming star gazing at nighttime, boat...

  • Charleston
  • 5 Bedrooms
  • 2 Bathrooms
  • Sleeps 10
The Palmetto State Complex- 4 Condo Comp...

The PERFECT vacation rental for Weddings, Giant Groups and Families looking to travel in complete extravagant comfort and privacy! This 4-suite unit is the ONLY property in Charleston that can host your entire event in their own private suites just...

  • Charleston
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 24
Downtown Charleston Gem, Walk Everywhere...

Summary:Welcome to The Lavender & Sage Suites a attractively restored 6BR 6.5BA home that pairs modern luxury with timeless Southern appeal. Located in the heart of downtown Charleston, you're just steps from the city's best eateries, nightlife, and...

  • Charleston
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 12
The Grand Helène - Newly Renovated 11BD...

Summary:Freshly constructed 11BR/11.5BA home in the laid-back Cannonborough/Elliotborough neighborhood—ideal for enormous groups seeking space and privacy. The property features three separate units in one building, ideal for gathering together...

  • Charleston
  • 11 Bedrooms
  • 12 Bathrooms
  • Sleeps 22
The Madison Compound- Entire Charleston ...

Encompass yourself in the history of Charleston by staying in this freshly remodeled 1890`s single home. The Madison Compound offers guests all the aesthetic features of a Charleston Single House from it huge Piazzas, private roof top deck and...

  • Charleston
  • 6 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
8 Bedroom - Close to King Street - with ...

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...

  • Charleston
  • 8 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Gorgeous 6bd, 6ba Home, Made for Large G...

Summary:Welcome to your Charleston getaway, two standalone homes side-by-side, designed for groups who want space, comfort, and effortless appeal. Set in the heart of the city, you’ll be just steps from Charleston’s best dining, shopping, and...

  • Charleston
  • 6 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Rare French Quarter Escape, Sleeps 16 w....

Summary:Located in the heart of the French Quarter and draped in history, this private, secure 3,300 sq. ft. luxury getaway comfortably sleeps 16 guests with 5 roomy bedrooms, dual master suites, ensuite bathrooms, and upgraded luxury amenities...

  • Charleston
  • 5 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Guesthouse Charleston: SOUTH (105 ALL)

This combined listing for South 105 A, B, & 105.5 is a great space for huge groups. Each unit has 4 bedrooms, and 4.5 bathrooms totalling 12 bedrooms, 12 full bathrooms, 3 half bathrooms, 3 full kitchen/living areas. Located on the desired Spring...

  • Charleston
  • 12 Bedrooms
  • 13 Bathrooms
  • Sleeps 28
New Renovation - 5 Beds/5 Baths - 1 Bloc...

About this spaceALL NEW, completely refreshed home one block from King Street- 2 rooms w/ king beds, 3 rooms w/ queen beds, living room w/ king pullout couch- Flexible check-in / out times- Multiple private outdoor patios- 2 off-street parking...

  • Charleston
  • 5 Bedrooms
  • 5 Bathrooms
  • Sleeps 12
Downtown Duplex - Coming St - Sleeps 20

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...

  • Charleston
  • 6 Bedrooms
  • 4 Bathrooms
  • Sleeps 16