Whether you’re looking to visit Charleston in style for the weekend or are a local in need of an unforgettable staycation, we’ve compiled a list featuring 17 of some extraordinary rentals in our city that are worthy of a trip for you, your partner, the bestie, or the whole squad this year.
Just a heads up: Prices may vary depending on dates selected, taxes, and booking and cleaning fees (sorry, Airbnb and Vrbo make the rules, we just follow them).
Outdoor oases
Serene Cottage
Light and air are in abundance at this charming house.
- ~$353 a night
- 1 BD | 2 BA
- Heated salt water pool, courtyard, washer and dryer
- Bonus: Check out this sister rental.
Charleston Home with Rooftop Deck
If you’re looking for time in the sun, this property’s rooftop deck has plenty of seating and surrounding greenery.
- ~$339 a night
- 1 BD | 2 BA
- Fully stocked kitchen, washer and dryer, courtyard
Cozy Cottage
This guesthouse has tropical plants, a walled patio, and a clean, light interior.
- ~$165 a night
- 1 BD | 1 BA
- Fast wifi, self check-in, fully equipped kitchen
Pink is a neutral
Historic B&B and Speakeasy Suite
Book a stay in a suite in this bright pink bed and breakfast.
- ~$134 a night
- 1 BD | 1 BA
- Free bikes, speakeasy-style lounge on site, grab-and-go breakfast
The Little Pink House on the Peninsula
Colorfully designed rooms and elegant outdoor spaces are waiting for you at The Little Pink House.
- ~$339 a night
- 1 BD | 2 BA
- Linens and towels provided, smart TV, washer and dryer
Pretty in Pink Downtown Charleston Flat
A guest suite with bohemian flair.
- ~$197 a night
- 2 BD | 2 BA
- Washer and dryer, parking, linens and towels provided
Luxury stays
Executive Penthouse
Stay in this top floor luxury penthouse apartment with sleek finishes and dramatic splashes of color.
- ~$340 a night
- 2 BD | 2 BA
- Fully stocked kitchen, dining seating for eight, private side piazza
Luxury Pied-à-terre
Step into chic design, French doors, and light and air in this townhome.
- ~$453 a night
- 2 BD | 2 BA
- Self check-in, linens and towels provided, parking
Charming Downtown Home
A spacious home decorated in a pastel palette with a spiral staircase.
- ~$289 a night
- 1 BD | 1 BA
- Linens and towels provided, wifi, King size bed
Charming mid 1700s Kitchen House
A house with brick detail, wooden beams, and a shared courtyard and fountain.
- ~$500 a night
- 2 BD | 2 BA
- Patio, indoor fireplace, fully stocked kitchen
Designers’ dream homes
Interior Designer’s Historic Guest Retreat
No luxury was spared in this 1810-built home owned by a professional interior designer.
- ~$395 a night
- 1 BD | 1 BA
- Fireplace, fully stocked bar, free-to-use bicycles
Glamorously renovated downtown home
A clean and comfortable yet eye-catching interior awaits inside this little green house.
- ~$448 a night
- 2 BD | 1 BA
- Linens and towels provided, grill, beach chairs and towels
Fully Renovated Bungalow
This 1905 Victorian duplex home was renovated with professional interior design in January 2022.
- ~$301 a night
- 2 BD | 1 BA
- Linens and towels provided, washer and dryer, parking pass
Downtown Charleston with Courtyard + Porch
This house is stylish both indoors and outdoors with a great location.
- ~$179 a night
- 4 BD | 2 BA
- Self check-in, porch, parking
Bungalows and boho
Gorgeous, Bright, Luxurious Apartment in Historic Downtown
What more could you need than this snug and brightly decorated Charleston home?
- ~$410 a night
- 2 BD | 2 BA
- Linens and towels provided, parking, veranda
Charleston Boho Bungalow
The secret to an ultra-cozy weekend: staying in a bugalow.
- ~$118 a night
- 1 BD | 1 BA
- Outdoor tub and shower, fire pit, grill
The Little Blue House
This house has everything you need with games, laundry, and outdoor space.
- ~$85 a night
- 2 BD | 1 BA
- HDTV with Fire TV, washer and dryer, grill
