Holiday rentals with outdoor seating in Charleston

Boho Bungalow | Private Oasis, Heart of Downtown

Escape to this enchanting brick cottage just moments from the harbor where historic charm meets modern comfort. Cozy up in the inviting living spaces with warm tones and exposed brick or relax in the private garden just outside. A charming bedroom awaits and you’ll adore the fully equipped kitchen perfect for intimate meals. Wander down to waterfront parks eateries and scenic views all within walking distance. *NEW* Opening mid/end of March 26', the Boho Bungalow will have a private dipping pool

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.

Only 3 Blocks from King | Backyard! | The Felix

Stay in this beautifully revamped first-floor Charleston Single, where classic Southern charm meets modern comfort. This bright 2 bedroom, 2 bathroom home offers an inviting place to relax while being perfectly positioned for exploring the city! Just three blocks from King Street, a 15 minute walk to the College of Charleston, and about 20 minutes from both Charleston International Airport and the local beaches, it’s an ideal home base for your Lowcountry getaway. Permit Number: 06252

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

Spacious Daniel Island Apartment

Fully furnished 1 bedroom (queen bed) apartment on Daniel Island. We are able to bring a single mattress out to the apartment for guests bringing a child, so the apartment can accommodate up to three (two adults and a child). Full kitchen with glass cook top, dish washer, full-sized refrigerator/freezer, toaster oven, etc. Includes linens, dishes and utensils. Washer/dryer en suite. Has Youtube TV, HBO Max, and wifi. 15 mins from airport, downtown Charleston, and beaches.

Serene Courtyard • Parking • 2 Blocks to King St!

✨ Welcome to Azaleas on Spring – Suite C! 🌺 Notable amenities include: 🌿 Secluded Private Patio 📍 2 Blocks to King St – Walk to Charleston’s Best Dining, Shopping & Nightlife 🛏️ 2 King Bedrooms + 2 Ensuite Bathrooms 🚙 On-Site Parking for 2 Vehicles 😴 Comfortable Mattresses 📺 Smart TVs – Streaming Included! 🛜 High-Speed WiFi + Desk 🫧 Washer/Dryer 🍳 Fully Stocked Kitchen ☕️ Local Coffee Provided 🚿 Hair Tools in Bathrooms 🎶 Record Player + Game Console

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.

Hawk’s Nest minutes to Charleston/Folly Huge Deck

This bungalow is located on 2nd floor hidden in a grove of oak trees. The unit has been completely renovated and bathroom and kitchen have granite countertops and stainless steel appliances. There is a king size bed in the main bedroom. Two large sofas can provide comfortable space also There is a huge deck with table and adirondack chairs . The large living area open with plenty of light plenty of light and large yard provides privacy from street.

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.

Homel Place, Charleston

If you want to experience local living in downtown Charleston, this is your place. This private guest suite in a 100-year old home is tucked away on a quiet alley, between lovely and historic Hampton Park and upper King Street. This lock-off suite includes a comfortable queen size bed, a sizable full bathroom, mini fridge, coffee station, dining area, and small outdoor patio. Park in the driveway steps away from your private entrance.