Holiday rentals with breakfast in Charleston Harbor

4.85 out of 5 average rating, 325 reviews

Trendy Downtown Upper King Area~Rutledge Retreat B

In the emerging area known as Cannonborough/Elliotborough. Built in the 1800's but all modern conveniences. In renting this newly renovated 2 bedroom apt you will find yourself within blocks of historic parks, sites, stores, restaurants, bars & all that the revitalized Upper King has to offer. NOTE: This is a 2 person/1 BDRM Booking Rate with full, private use of all common spaces with one BRM blocked. A $25 per person, per day for all persons over 2 includes use of both BRMS. Sleeps 1-4 people.

Guest house in Summerville

4.98 out of 5 average rating, 719 reviews

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

4.96 out of 5 average rating, 142 reviews

Cottage in Charleston

Southern Cottage between downtown and beaches

Newly renovated cozy cottage provides the Low Country experience you & your family are looking for. Enjoy Riverland Terrace, a quiet & hospitable neighborhood centrally located in Charleston. Only a short 10 min drive to downtown, 15 min to Folly Beach, & 20 min from the Charleston International Airport. Kitchen is fully stocked, the coffee bar includes coffee and Nespresso pods. Grocery stores within 2 miles. Comfortable King, Queen, Full & 2 twin beds. Free parking, fast wifi, pet friendly.

5 out of 5 average rating, 22 reviews

Downtown Home: Rooftop, Breakfast, Walker's Dream

*Welcome to Your Perfect Charleston Getaway with Rooftop overlooking Charleston!* BREAKFAST Foods INCLUDED, see details Eggs Bagels Fruit: Blueberries, Strawberries, Bananas (based on seasonal availability) Granola/Cereal Yogurt Organic Milk Creamer K Cups Orange Juice Tea Bags Bottled Water Off street parking -4 Bedrooms with 5 bathrooms and 2 Bonus Rooms -Sleeps 13 guests comfortably -Gourmet Kitchen - Contactless check-in and check-out -Washer/Dryer **We can’t wait to welcome you!**

Superhost

5 out of 5 average rating, 7 reviews

Stylish Coastal Home + Custom Pool

Welcome to our modern luxury home — thoughtfully designed for comfort. Featuring 2 king bedrooms, spa-like baths with soaking tub and dual showers, a chef’s kitchen with Dacor appliances, and a cozy fireplace in the master suite. Enjoy the (ready July 12) pool, hot tub, gas fire-pit, and basketball court. We created this home to be a true retreat, not a typical rental, and we love sharing it with guests who appreciate beautiful spaces and want to feel at home on their vacation. #LIC061288

Guest suite in Charleston

4.99 out of 5 average rating, 397 reviews

The Garden Folly Guest House

Our architect said, “this is NOT a garage, it’s a Garden Folly!” Our Guest House has a bird’s eye view of the rose covered pecan tree and a vista of the marsh and the Wappoo Creek. When we rebuilt our 1930's garage we saved all the beaded siding and pine floor. My husband enjoyed incorporating many design elements and creative ideas. It was quickly becoming the Taj Garage. We decided it was just the kind of property we enjoy when we travel, so, Voila! we decided to share it with you!

4.91 out of 5 average rating, 129 reviews

Home in North Charleston

Katie's House

Open concept, living room, dining, fully stocked kitchen 3 bedrooms 2 baths, screened backporch, washer/dryer, self-check in. Outdoor security cameras. Central heating/air. Fast Wi-Fi. The house is a smart home with smart TVs, radio/CD player. CVS next door, dog park behind CVS. Airport 12 min, Amtrak 3 min Tanger outlet/Walmart/Sam's Club 8 min, downtown Charleston 17 min Beaches 20-30 min. Restaurants, Old North Charleston 3 min. North Charleston Short-Term Rental Permit 2025-0583

4.98 out of 5 average rating, 127 reviews

Home in Summerville

Summerville Fun Family Home! 4 miles 2 main st.

We are 4 miles from Hutchinson Square in the Jedburg section of Summerville. 30 mls. to DT Charleston.Cozy and inviting 1600 square ft home on half acre in quiet neighborhood. Family centered property w/ high chair, crib, baby monitor and more. 2 Full Baths, Open floorpan living/main area. Board games, smart TV's for entertainment. Enjoy a soak in the tub, relax by the firepit, Swingset and playhouse for the kiddos, Game room. We look forward to hosting you! Min age to book :23

4.97 out of 5 average rating, 145 reviews

Cottage in Johns Island

Pet Stay Free, Near Charleston and Kiawah!

This is an all outdoors vacation experience! Nature entertains you like a moving picture of your daily life. Relax in a private corner of our farm. Fish, paddle board, canoe, hike trails, watch horses, & bird watch. Or have a quiet dinner in our cozy space with a full kitchen. Bring your bikes to ride our trails. Once you book with us, a Grocery service is just a click away so your kitchen will be stocked with all your requests before your arrival. 2 pets allowed. ZSTR012501107

Guest house in Charleston

4.9 out of 5 average rating, 639 reviews

Cozy Cottage w Games, Firepit, Grill, and More!

Centrally located cottage perfect for exploring the wonders of Charleston! - Amazing location; quick drive to downtown, minutes from Avondale, 12 miles to Folly Beach. - On a beautiful 9 mile bike & walking path - Backyard oasis with games, firepit, grill, and outdoor dining space - Beach chairs, cooler, and umbrella available - Updated interiors with king bed, games, streaming, and fast wifi Enjoy the perfect home base to explore the Lowcountry. We can't wait to host you!

Superhost

Tiny home in Charleston

4.83 out of 5 average rating, 429 reviews

The Cashmere Guest Suite - PERFECT LOCATION!

SANITIZED THOROUGHLY BETWEEN GUESTS! Luxury private suite behind an historic home, the Cashmere Cottage is located in beautiful, Live Oak-filled Riverland Terrace - less than 3 miles from downtown & 8 miles from Folly Beach. You'll feel like royalty in this condensed space with luxury linens, fully ADJUSTABLE BED (!!), plush towels & robes, coffee bar with mini-fridge, & huge bathroom with a gorgeous frameless shower & salon-quality products to pamper yourself.