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Browse Select South Side Cottages

Enjoy al fresco dining with a grill and comfortable seating.

"The cottage is very whimsical and cozy. The view was amazing night and day. We enjoyed the fireplace and the French pastry shoppe La Gourmandine. We would rent this place again. "

Relax on the covered porch with a view of the surrounding neighborhood.

"Great location. Very clean. Worked perfectly for our group of 5 and dog. will definitely be returning,"

Stroll through a charming neighborhood with well-manicured lawns and a variety of homes, including a two-story house with a front porch and garage.

Staircase leads to a charming building with a naturalistic setting, surrounded by plants and rocks.

Rows of two-story homes with gabled roofs line the street.

"I wasn’t thrilled the rental was on a second floor when I had my dogs. Pets, unfortunately, tend to move freely and I thought the guests on the first floor below us may have been annoyed with that. I also didn’t like having to haul our luggage up many stairs, including heavy video equipment I brought with me for this scheduled trip to attend an event. I also received many emails and text messages reminding me about the trip; and overlooked that the instructions said our entrance was in the...

Relax on the covered porch with a view of the street, featuring a wicker chair and large windows.

Stroll up to this charming two-story home with a welcoming front door and cozy porch area.

Two-story house with a white picket fence and a well-maintained lawn.

"We had a really good time staying here- we enjoyed the game room and the firepit and the rooms were quite comfortable "

Stylish building with a flat roof and balconies, set amidst a beautifully maintained front yard with a gravel pathway and lush shrubs.

"Nice, well kept and easy to communicate with host/ owners. Would recommend! "

Relax in a well-read environment with a comfortable sofa, wooden coffee table, and a patterned rug.

Enter a cozy home with a small front porch and steps leading up to the entrance.

"Motion detector lights were very bright and non sense Hard mattress House older and dated"

Stylish two-story home with a front porch, outdoor seating area, and garage.

Stylish single-story home with a gabled roof and covered porch.

"The place was perfect for friend and I who were visiting Pittsburgh to watch the NCAA basketball tournament at PPG arena. Walking distance to restaurants but it is hilly. 8min uber to PPG arena. I really is like a cottage in the city… was pleasantly surprised to see a few Deer in the back yard every morning."