Holiday rentals in Round O

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.

★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*

Riverbank Cottage on the Edisto River

Riverbank Cottage is situated on the banks of the Edisto River. Our 630 square foot cottage is freshly remodeled and waiting for your weekend get a way or summer fishing trip. Fish off the bank or bring your canoe, kayaks or small fishing boat to enjoy the river. There is a boat landing in the neighborhood and just down from the cottage. This is a studio cottage that sleeps up to 4. Sit on the screen porch and enjoy the sunrise and river views. Full kitchen and bathroom. No bedrooms.

White Pickett District Loft

Welcome to our charming White Pickett District loft nestled in the heart of historic downtown Summerville! This cozy retreat offers a private one bedroom, one bath with kitchenette, perfect for couples or solo travelers looking to explore the beauty of South Carolina. WPD is just steps away from the town’s rich history and culture. Whether you’re here for a weekend getaway or an extended stay, WPD offers the perfect blend of comfort, convenience & charm for unforgettable experience!

Guest House/Villa

Enjoy your stay at this immaculately designed new build Villa. Located on a family property surrounded by 2 acres of trees, in a quiet rural neighborhood. Lots of privacy, peace and quiet, yet only 5 minutes from restaurants and stores. 15 minutes from Downtown Summerville, 40 minutes from Charleston and various coastal attractions. The villa is separate from main house and has no shared space other than the driveway. NO smoking, No pets. Laundry service available for long stays.

Low Country Loft in Ridgeville.

Enjoy a quiet and comfortable stay in Ridgeville. Sitting on 10 acres you can enjoy relaxing nights on the back porch or during the day enjoying the woods filled with birds. This quiet neighborhood is a 15 minute drive to Summerville, 50 minutes to historic Charleston, and 50 minutes Folley beach. The barn is well equipped for longer stays and boasts sleeping for up to 7. 1 King bed, 2 queens and a rollout bed. This is new construction in 2024 and is very comfortable.

The Cozy Casa

Whether looking for a place to rest during your travels.. or staying in the area for a while, the Cozy Casa is the perfect choice! Stylish, clean, affordable, premium linens, very well stocked, 1.5 acre fully fenced yard, and located just a 2 minute drive off of Exit 53 of I- 95 in Walterboro, SC. Just a few minutes drive to everything! The Cozy Casa is a stand out Short Term Rental that truly takes hospitality seriously. Come and enjoy this very well appointed home.

Cottage in the Oaks

Cottage in the Oaks is truly a dream cottage. Our goal was to make this cottage a restful, peaceful home away from home. We are nestled on 2.5 acres with multiple ancient Live Oaks. You will feel as though you are in a country setting but are only a 2 minute drive to the center of Historic Summerville, with multiple choices of restaurants, local shops and of course bars. Play pickleball? We know all the local courts and teams, we are happy to help you find a game!

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.

Cute Frog

This unique place has a style all its own. This is a furnished room over detached garage 🐸. Open floor plan with queen-size bed, private bath and sitting area. Amenities include small refrigerator, kuerig coffee maker and microwave. A quaint deck with cafe table and chairs. No smoking inside. 45 minutes to downtown Charleston, 30 minutes to historical plantations and 10 minutes to historical downtown Summerville.

Full Kitchen, 2 Bed, 2 Bath W/ Laundry & Fish Pond

Hosted by a Superhost with multiple listings in Summerville, this charming, two bedroom, two bathroom apartment features a full kitchen, a washer/dryer combo, and a picturesque 1 acre fishing pond. Resting on a small farm on the outskirts of Summerville, this one-of-a-kind shabby-chic suite will have you in a southern state of mind in no time. Just don't be surprised if you see a chicken or two running around...

Adorable Small, Clean Home

🚭 Zero tolerance policy for smoking/vaping on the property, even outside. We appreciate your respect by not booking/requesting/inquiring our place if you or any other guests are smokers. Also, due to allergies, we cannot accommodate animals of any size or kind. This listing is for the main house only, the detached guest house is a separate rental.