Family-friendly holiday rentals in Shadyside, Pittsburgh

Andi’s place worked out perfectly for our sisters weekend. For 5 people everyone could have their own bedroom and there was enough sitting space for us all. Plenty to do with restaurants, museums and parks within walking distance or a short drive, then once home the house was quiet. Recommend!

We had a good stay for grad weekend for my daughter. Enjoyed the place, the nice TV, the many snacks provided and the back garden.

Our stay was absolutely terrific! Rick was an incredibly attentive host, reaching out days before our arrival to make sure we were familiar with the entry system and had everything we needed for a smooth, stress-free start. We were welcomed with fresh flowers, a wonderful basket of snacks and a fantastic list of his favorite local spots, which we really appreciated. The home itself was spotless, beautifully maintained, and equipped with every modern amenity we could ask for. Rick checked in with us periodically to ensure we were comfortable and had everything we needed, without ever being intrusive. The location couldn’t have been better—nestled on a charming street in a lovely neighborhood, within easy walking distance to shops, restaurants, and essentials. It was a perfect home base for visiting the University of Pittsburgh and getting downtown quickly and easily. Highly recommend this stay—we would absolutely return!

Always a joy to stay here (which we try to do every time we come to town). The house is comfortable, well-furnished, and always spotlessly clean. And it’s a real home, not a soulless, cookie-cutter Airbnb rental. Plus, Laura is a delightful host, super friendly and very responsive. Don’t hesitate.

Good location. Walkable to some local spots but also easy to uber to other areas. Spacious for a group. It rained most of the weekend but there’s a great outdoor space! Beds were very comfy! Super cute decor, modern. Fantastic kitchen. Awesome large round table that is great for a group or game night. Lots of bathrooms. The only complaint is the lock to the front door is a little temperamental —takes awhile for it to lock and unlock. Either way—minimal inconvenience for a near perfect experience. Would definetly stay there again!!!!

Great stay for the weekend for my brothers bachelor party. For the start Johnathan and Brian were very helpful and understanding. They made it very easy to start the weekend off well. We needed a little bit later checkout and they were very accommodating with that among several other things. Would highly recommend staying with Jonathan and Brian!!

Carlos's place was great! There was plenty of room for myself and my family. We loved the decor and would recommend the house to anyone needing a place to stay in the area.

Having stayed in a number of Air BnBs over the years, Heidi’s home moves to the top of the list of favorites! We really appreciated the opportunity to stay in Heidi’s beautiful home, where we were treated with kind hospitality. The house is even better than in the photos, so lovingly maintained, with incredible original woodwork and stained glass. After a day of activities in the Pittsburgh area, it was fantastic to come back to this amazing house, which is super comfortable and homey. Not only was the house great, but Heidi provided us with food! It was so awesome to have fresh coffee and a nice breakfast in the morning. She also gave us helpful suggestions for area restaurants and brew pubs within walking distance. I especially loved the front porch for taking in the night air on the porch swing…We highly recommend this beautiful home!

Rebecca was very communicative. She was very flexible and understanding of several date changes that we had to make due to family emergencies that we had experienced. The location had great access to 376, the Homestead Waterfront, and Squirrel Hill shops and restaurants.

Great spot and beautiful view of the city! Beds were very comfortable and there was a lot of space. The place is a little dated but clean.

It was wonderful spot, a lot of restaurants and things to do in walking spots. Neighbors were really friendly and helpful! Michael was super understanding and communicative. We ran into a problem he helped.

We came into town for the US Open. Cabin was easy to find and a great location for us to get to the tournament. Diane was very responsive to any message. Loved the peacefulness of the cabin. We enjoyed sitting on the deck and watching nature. Thank you Diane.

We stayed at Avi's listing in July 2024 while attending a 10-day yoga teacher training in Squirrel Hill. From the original booking and all of the way through our final day, Avi was responsive and helpful in our communications. The listing looks exactly as it does in the photos and there is free street parking. Walkable to many restaurants and parks in the surrounding area and a 15-20 minute drive from downtown Pittsburgh. We experienced a few issues during our stay that couldn't be immediately addressed by Avi and he very quickly found someone to help remedy the situation. The issues were not his fault, yet he made the situation right and offered exemplary customer service. I will definitely keep Avi's listing in mind for my future visits to Pittsburgh!

Bloomfield is the Little Italy 🇮🇹 of Pittsburgh. The unit is a very large 1 BR. It is very private, yet within a block of several restaurants.

Gail was friendly & responsive and available to answer my questions. I came into town for a Steelers game and Gail’s place is about a 20 minute walk to the stadium. I’m glad I walked because I got to see all the tailgating along the way! There’s a great coffeeshop two minutes away; and my Ubers came quickly. There’s also an Aviary nearby that I wish I had more time to visit. Gail’s neighborhood is safe and the people in Pittsburgh are super friendly! 💛

Great place. This is the place we will get whenever we come back to the area.

Loved the proximity to the overlook. Quiet neighborhood. Downstairs bed was a little hard for me. Enjoyed the outside front porch deck. Bigham tavern was good and a short walk. Parking in the driveway is a little sketchy so we parked in street. I would stay here again.

Great location walkable to some good spots including the Arsenal area and some watering holes. Easy, quick rideshares to the Strip and downtown including the arenas and stadiums. Plenty of space inside. Just be careful heading down the stairs.

This AirBnB is a wonderful place to stay with family! The location is calm, walkable, safe and peaceful - seems to be a residential community with a lot of families. The place is as good as it looks in the pictures! It is very well maintained, super clean and well-equipped with everything you would ever need while traveling! It is also very well furnished with modern aesthetic interiors. Everything in this house, right from the beddings/mattress up until the soaps and hand wash are all of great quality! Extremely comfortable and overall an amazing place to stay! The host is also extremely helpful, friendly and accommodative. Had a very memorable stay overall, would 10/10 recommend!

We had a wonderful stay. The house was as advertised. 15 min from pretty much anywhere. There were 5 adults and 2 children. We had plenty of space. We loved reading the binder, explaining the homes history. Made the home that much more interesting to us! You will not be disappointed if you chose to stay at this home.