Holiday rentals in Round O

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Top-rated holiday rentals in Round O

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Top guest favourite
The living area features a mix of modern and whimsical design, highlighted by a vibrant blue wall and a neon Pegasus light. A plush velvet sofa and coordinating armchairs surround a central wooden coffee table, with a colorful area rug underfoot. Large windows allow natural light to fill the space.
Guest house in Summerville
5 out of 5 average rating, 83 reviews

2 King bed 2 Bath*Walkable* Downtown Summerville

Hidden away amidst lush azaleas and towering pines, you will find yourself at the heart of small-town Southern Living. This two-story Guest House provides you with the perfect combination of secluded garden landscapes and downtown accessibility. Modern amenities and a whimsical interior design will make your stay in our charming cottage a time to remember. You'll be within a short walk of local shops and restaurants and an easy drive to downtown Charleston and surrounding beaches and attractions

Top guest favourite
An airy loft space features a suspended wooden swing, inviting relaxation under the high, timbered ceilings. Natural light streams through large windows, illuminating cozy furnishings including a bed and a dining area with a wooden table. Unique decor elements enhance the overall character.
Guest house in Summerville
4.98 out of 5 average rating, 762 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*

Top guest favourite
The exterior of Riverbank Cottage is shown, featuring a red metal roof and a wooden deck. The cottage is surrounded by trees and greenery, with a gravel area in front and additional buildings positioned in the background.
Home in Ridgeville
4.96 out of 5 average rating, 51 reviews

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.

Top guest favourite
A cozy seating area features a soft armchair and a tufted ottoman, positioned near a stone fireplace. Built-in shelves display decorative items and books. Expansive glass doors provide natural light and a view of the outdoor space, enhancing the inviting ambiance.
Guest house in Summerville
4.98 out of 5 average rating, 60 reviews

Cottage 1 king bed, 1 set bunk beds, heated pool

Escape to a cozy, beautifully furnished cottage nestled in historic Summerville, just a stroll away from the heart of the town. Whether you're a couple seeking a romantic getaway or a small family looking for a peaceful home base, this cottage offers the perfect blend of comfort, character, and convenience. The patio is ideal for relaxing mornings or evening meals under the stars. With easy access and free parking, it's perfect for day trips to the beach, Charleston, or a walk into town.

Guest favourite
An aerial view captures a lush, green landscape surrounding a charming property nestled along the Edisto River. The expansive yard is framed by diverse trees, with a small boat dock visible at the water's edge, inviting exploration of the serene river environment.
Cabin in Ridgeville
4.94 out of 5 average rating, 86 reviews

River Front Cabin Estate on the Edisto River

Welcome to our beautifully fully furnished Edisto River Front retreat. Just 1 hour outside of downtown Charleston and 15 miles from downtown Summerville you can find our charming 4 acre gated river paradise with a private fishing lake and direct river access to the Edisto River. If you are looking for relaxation and river adventures, this is the spot. Fully furnished with new appliances, 150mbps fiber internet and cell phone reception. Direct private river access with canoes and kayaks.

Top guest favourite
The exterior of the villa is shown, featuring a light-colored stucco façade contrasted by large windows. Surrounding landscaped areas include planters with vibrant greenery and flowers. A gravel pathway leads to the entrance, framed by the natural beauty of trees in the background.
Home in Summerville
4.92 out of 5 average rating, 173 reviews

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.

Top guest favourite
A newly constructed barn is illuminated at night, showcasing a sleek white exterior with a metallic roof. The garage doors are highlighted by warm lights, and soft illumination surrounds the building, creating a serene atmosphere among the surrounding trees.
Barn in Ridgeville
5 out of 5 average rating, 82 reviews

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.

Top guest favourite
A spacious bedroom features a black metal bed frame adorned with white bedding. Two stylish chairs are positioned beside large windows offering views of the surrounding landscape. A wooden dresser and a woven area rug add elements of comfort and warmth to the room.
Guest house in West Ashley
4.98 out of 5 average rating, 246 reviews

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

Top guest favourite
A charming cottage is surrounded by vibrant azaleas and lush greenery. The inviting porch features comfortable seating with a view of the flower-filled garden, creating a peaceful outdoor atmosphere. Tall trees provide shade, emphasizing the serene country setting.
Cottage in Summerville
4.97 out of 5 average rating, 287 reviews

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!

Top guest favourite
A scenic view of the Edisto River is captured from the deck, featuring four high chairs along a wooden bar. Lush greenery lines the riverbanks, while the calm water reflects the surrounding landscape.
Home in Cottageville
5 out of 5 average rating, 35 reviews

Serendipity (erst Country Cove)

Serendipity awaits on the Edisto River. Lovingly updated with your comfort in mind. Experience all the river has to offer while staying at this serene 2 bedroom, 1 bath waterfront rental in Cottageville. This charming cabin is the perfect place to experience relaxation with loved ones. Spend your day fishing, kayaking , sipping coffee overlooking the water, roasting marshmallows at the fire pit or simply soaking up the sun . Memories are ready to be made.

Guest favourite
A spacious home is set against a backdrop of green grass and trees. The structure features a central entrance with wooden steps leading up to a front porch. Flanking sides showcase symmetrical windows and a neutral-colored exterior.
Home in Walterboro
5 out of 5 average rating, 11 reviews

Maple Ridge Retreat

Forget your worries in this spacious and serene southern sanctuary. Maple Ridge Retreat is a great place to relax with the whole family. The home has space to accommodate larger groups and is kid friendly with . This gorgeous place offers a comfortable front porch for eating or just relaxing and a huge fenced in backyard. Just 45 minutes from Edisto Island and Summerville, SC and an hour to Charleston, SC and Savannah, GA. Conveniently located near I-95.

Top guest favourite
An inviting guesthouse is surrounded by lush greenery and vibrant pink flowers, showcasing a wraparound porch with white railings. Tall trees and palm plants create a serene and natural setting, while soft sunlight illuminates the charming structure.
Cottage in Johns Island
4.97 out of 5 average rating, 430 reviews

Captain's Quarters

Nestled at the end of an avenue of Live Oaks, our lowcountry guesthouse offers a peaceful retreat with all of the modern conveniences. Our property is home to beautiful birds, turkey & deer. We are centrally located with easy access to downtown Charleston, Folly, or the airport in 20 minutes, 20 minutes to Kiawah, Seabrook and Wadmalaw Islands. Dinner nearby at Johns Island restaurants, Wild Olive/Royal Tern, or cook up your own fresh catch of the day!

Popular amenities for Round O holiday rentals