Holiday rentals with outdoor seating in Charleston

Adorable Guesthouse - Bikes + Parking!

Live like a local while in Charleston in this unique home! You will be amazed at what all is found within this cottage next to the main house built in 1895. Quaint & perfect for your stay. Relax after a full day of sightseeing in your private Charleston patio. ♥ 1 bedroom | 1 bathroom | 1 Queen bed + Roll up mattress ♥ Charleston Style Patio ♥ Easy Walk to King Street (Walk Score of 99) ★ Bedroom + Living Area w/ Smart TVs ★ Outdoor Courtyard w/ Seating + Bistro Set ★ Off-street Parking ★ Bik

The Backpacker

Our "Backpacker" is a cute and cozy 96 sq.ft. of tiny house nirvana. Situated on a small tidal slough, it provides a beautiful natural setting for reflection and appreciation of that which is good in life. For those looking for luxury, the Backpacker is not for you (you may encounter bugs and it's really hot in summer). However, the Backpacker has a pretty cool vibe, and is extremely convenient to historic Charleston and Funky Folly Beach. The Backpacker is for backpackers and nature lovers.

Historic Vintage Charm | Private Modern Luxe

Turn back time in this refined historic Charleston residence (OP2025-06356). Soaring 12-ft ceilings, polished wood floors, and grand sash windows set the tone for an elegant retreat. A master bedroom and curtained sunroom each offer king beds for flexible sleeping. Located in a quiet, walkable historic downtown neighborhood. Perfect for couples or a sophisticated girls’ weekend. Private entrance, thoughtfully designed 1,000 sq. ft. interior. Exclusive off-street parking with EV charger.

Wagener Terrace Courtyard Apartment

Welcome to our renovated, well appointed 1 bedroom apartment located in the Wagener Terrace neighborhood. You will have a king bed and the full kitchen has basic cooking supplies. Dedicated driveway in front leads to a private courtyard entrance. Our apartment is walkable to Lowndes Grove and Hampton Park. We are 1.5 miles from the start of "downtown". Generally, parking is not a problem, but lots of people choose to Uber or Lyft or ride Lime bikes. Owners live in the connected main house.

Coastal Charm: Village Hideaway

Charming two- bedroom, one bathroom cottage tucked away in a quiet neighborhood located close to both nature and local attractions. Our cottage was a thoughtfully designed space with attention to detail in every corner. We offer a fully equipped kitchen with modern appliances and a breakfast bar. PLEASE note, as a reminder to house rules: no smoking, vaping, e-cigarettes, or pets allowed in or outside of property. Owner has severe allergies. Thank you. STR Permit #: 250271 BL#: 20127320

Cannon St. Suite D

Location Location Location this upstairs one bedroom apartment renovated to the studs in 2015 right in the heart of down town Charleston. Located at Cannon apartment D is walking distance to some of Charleston's best shopping, renown restaurants, bars, historic district and MUSC. This apartment boasts beautiful new hardwood floors, new cabinets, stainless steel appliances, stackable washer-dryer, new furniture outfitting the entire apartment, front balcony and two onsite parking spots.

Cozy Townhouse 5 mins from Magnolia Plantation

This recently renovated townhouse is located in the heart of West Ashley amidst a nice quiet neighborhood. As you enter you will find a living room with a gorgeous fireplace, smart TV, and a cozy couch. A full kitchen, washer/dryer, backyard, and parking for 2 are there for your convenience. You are conveniently located to Downtown, Tanger Outlets, Airport, Historic Plantation District, and Folly Beach. Regardless of your choice of activity, you will be comfortable and have fun!

Endless Summer Downtown CHS

This historic property was built in 1838 with original porches to this grand Charleston home. Full renovation in January 2023 to create the beachy, coastal, surf chic spot it is today. Updates include new kitchen, two new bathrooms & fresh paint. Relax surrounded by a fun vibe and great local art. Downtown dining and bars are a short stroll away but we are still tucked in the quiet neighborhood close to MUSC Hospital. Walkable to Upper King Street nightlife and dining.

Large Guesthouse with Private Dock & Marsh Views

This newly built carriage house is separate from the main house. The cottage is about 1,200 sqft so it very open and spacious and great views of marsh and our tidal creek. We have a separate work area with desk and a massive dinning table if you need more room to work or to gather with friends. Full kitchen, washer and dryer, massive shower, the list goes on. You may not want to leave! Feel free to go sit and have coffee or cocktails on the dock. PERMIT# OP2025-06925

Downtown Charleston abode w/ bikes, 4 Beds

Welcome to our chic 2 bedroom + 2 bath second floor unit just steps away from Charleston's historic Hampton Park. Enjoy sunset bike rides, 5 minute walks to downtown's hottest restaurants, and views of the Citadel from your front porch. This stylish home comes equip with a fully stocked kitchen, beach towels, games, baby equipment, workspace, washer/dryer, WiFi, off-street parking, bikes, and much more! Live like a local in Charleston's most coveted neighborhood.

The Parlor | 1BD w/ Huge Porch, King Bed + Parking

Unwind and enjoy generous space in this historic retreat. A large private piazza overlooking the backyard offers the feeling of having your very own Charleston dream home. Built circa 1850 and converted to apartments over a century ago, this farmhouse features expansive rooms with original moldings, mantels, and hardwood floors. A thoughtful restoration blends modern conveniences, like an updated kitchen and bath, with the timeless charm that defines Charleston.

Silverlight Cottage in Park Circle

A spacious retreat (780 sq ft.) in Park Circle: Elegant, gracious + charming. Brand new custom built guest house designed with a nod to classic Charleston architectural influence: open concept indoor - outdoor space to large shady screened porch where a perpetual breeze from the not-too-distant coastline blows gently all year round. Visitors will return from their travel deeply restored and revived - having experienced well-appointed accommodation.