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60 rentals found
Guesthouse Charleston: WEST (62 & 64)

West 62 and 64 are two striking homes located next door to each other, sharing a roomy outdoor courtyard ideal for calming with drinks after a day of exploring Charleston. Each home offers generous living spaces, sizable bedrooms, and multiple...

  • Charleston
  • 8 Bedrooms
  • 9 Bathrooms
  • Sleeps 24
Thomas Waring House | Sleeps 23 | Multi-...

Summary:Welcome to the Thomas Waring House at The Preserve, a historic and award-winning residence that offers a unique blend of appeal and modern convenience. Comprising 4 separate units, this broad property features a total of 11 bedrooms and 11.5...

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  • 11 Bedrooms
  • 11 Bathrooms
  • Sleeps 23
Blue Magnolia | Perfect for Large Groups

Summary:Discover Blue Magnolia, your classy 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...

  • Charleston
  • 7 Bedrooms
  • 4 Bathrooms
  • Sleeps 17
3 Luxury Houses w/ Patios | 1 Block from...

Summary:Discover luxury set of three completely refreshed luxury homes ideal for a sizable 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
  • 12 Bedrooms
  • 10 Bathrooms
  • Sleeps 30
The Inns | Luxury Design w. Speakeasy Ba...

Summary:Surrounded by swaying Spanish moss in one of Charleston’s most beautiful neighborhoods, this striking 7-bedroom, 5-bath home captures the essence of Southern grace with a modern twist. Thoughtfully remodeled in September 2025, every detail...

  • Charleston
  • 7 Bedrooms
  • 5 Bathrooms
  • Sleeps 14
Guesthouse Charleston: SOUTH (82 A & B)

82 A & B is a roomy two-story home, appealingly 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
The Edisto River Complex- 4 Condo Comple...

The PERFECT vacation rental for Weddings, Enormous Groups and Families looking to travel in complete extravagant comfort and privacy! This 4 Condo- 8 Bedroom/ 8 Bathroom Complex is the ONLY property in Charleston that can host your entire event in...

  • Charleston
  • 8 Bedrooms
  • 8 Bathrooms
  • Sleeps 24
The Chapel | Premier 13BR Estate in Down...

Summary:Welcome to The Chapel, a majestic 13-bedroom estate in downtown Charleston where beauty, space and heritage combine to create an memorable stay. Ideal for sizable families, weddings, get-togethers or special gatherings, this property offers...

  • Charleston
  • 13 Bedrooms
  • 12 Bathrooms
  • Sleeps 16
The OakTree | Stylish Bohemian Downtown ...

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

  • Charleston
  • 7 Bedrooms
  • 7 Bathrooms
  • Sleeps 16
2 Luxury Homes w/ Patios | 1 Block from ...

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

  • Charleston
  • 8 Bedrooms
  • 7 Bathrooms
  • Sleeps 20
Guesthouse Charleston: SOUTH 105 ALL

This combined listing for South 105 A, B, & 105.5 is a great space for sizable groups. Each unit has 4 bedrooms, and 4.5 bathrooms totaling 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
Luxurious KING Suite With New HEATED POO...

Summary:The Inn at 257 is located in the handsome Elliotborough neighborhood. You will be FOUR short blocks from King Street. We recommend you leave your car parked in our lot and appreciate the city on foot, bicycle, or the ever convenient Uber...

  • Charleston
  • 9 Bedrooms
  • 9 Bathrooms
  • Sleeps 2
The Manor | 8BR Home in Downtown Charles...

Summary:Step into this gorgeously 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...

  • Charleston
  • 8 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Guesthouse Charleston: SOUTH 105 A & B

Located peacefully on coveted Spring Street, this beautiful standalone duplex features eight roomy bedrooms and eight full bathrooms, just steps away from Cannon Green and just three blocks to historic King Street. Ideal for sizable groups or...

  • Charleston
  • 8 Bedrooms
  • 9 Bathrooms
  • Sleeps 20
Guesthouse Charleston: WEST (242 B & C)

West 242 B and 242 C are two beautiful standalone homes located in the heart of Charleston's vibrant Cannonborough/Elliotborough neighborhood, just two blocks from historic King Street. This prime location offers painless access to Charleston's best...

  • Charleston
  • 8 Bedrooms
  • 6 Bathrooms
  • Sleeps 16
Ivy Manor | DT Oasis + Carriage House!

Summary:Welcome to your Charleston getaway where artistry meets comfort and privacy. This stay features a main home plus a private carriage home, offering space, style, and a sense of getaway. Ideal for families or groups wanting design-forward...

  • Charleston
  • 8 Bedrooms
  • 4 Bathrooms
  • Sleeps 16
Cocktail Club | 4 Redesigned Suites

Permit Number: 05591The Space: Appreciate gracious Southern living in our cavernous 8 BR home. The home is divided into four delightfully designed 2 BR units, making this property ideal for sizable groups. Each unit has been thoughtfully decorated...

  • Charleston
  • 8 Bedrooms
  • 4 Bathrooms
  • Sleeps 17
The Inns | Grand 9BR Home in Downtown | ...

Summary:Welcome to your Charleston getaway, a enormous 9-bedroom haven designed for groups who value space, style, and connection. Recently modernized with fresh paint, brand-new beds, and crisp linens, this luxury mansion offers two full kitchens...

  • Charleston
  • 9 Bedrooms
  • 6 Bathrooms
  • Sleeps 16