Kid-friendly holiday rentals in Shadyside, Pittsburgh

Highly recommend this place! It’s in a great spot to get to all the cool place in shadyside. This is a very charming home. Elizabeth was such a sweet person to chat with during check in. She was very clear with what to expect and my stay felt more like staying with family.

Meredith’s house was an absolutely perfect spot for our family in our long weekend in Pittsburgh. Perfect location in an amazing location with all the amenities you could possibly imagine. Our 3 year old daughter loved the extra toys and books as needed. We come to Pittsburgh yearly, and we WILL be back.

The apartment was beautiful with an amazing view and we had a great time!

When I reached out for some coffee pods at 9:00 PM — they were at the front door within a half hour! I couldn’t believe how responsive Prafful was. The only suggestion I would have is for a small AC unit for the 3rd floor. The kids loved watching TV up there but it got warm. There were some fans available but in the heat of the summer they may not be enough for a good night’s rest. Other than that we found this house very accommodating and we had a memorable time. I loved the area too. Checkout was a breeze which was much appreciated.

Cortney’s place is a fantastic spot. The host is incredibly responsive, welcoming, and thoughtful. The house is spotless, cozy, and well-equipped with everything you might need to feel right at home. It’s conveniently located near bus routes, and it’s also walkable to great restaurants and shops in the Shadyside and Oakland area. I’ll definitely stay there again next time I’m in Pittsburgh!

Stayed here for over a month, it’s a cozy place for long time stay. Sesan is a great host, easy to communicate and really responsive.

Quiet peaceful neighborhood. Nice kitchen and set up. Sleeping 8 is a push, unless everybody is sharing a bed. Very clean, with lots of street parking.

I had a great two-night stay in Pittsburgh. The place was comfortable, easy to access, as described, and it was nice to be able to park in back. The bed was very comfy. The neighborhood was cute and quiet, but not far from downtown and things to do. I was not in Pittsburgh for long but would definitely stay here again if I return.

We loved staying at Edie's place again. The off-street parking is a plus and everything is so walk-able from the apartment. It was clean and so quiet.

Our family stayed at John's place during this Memorial Day weekend, and it truly exceeded all expectations. The apartment is super clean, bright, spacious, and very comfortable. Its location is ideal— just a short walk to the Carnegie museums and a large nice park, and within a short drive to downtown. The neighborhood is very safe, peaceful, quiet, and charming, with easy access to local shops and many nice dining options. John is a great host, he provided clear instructions and thoughtful touches that made us feel right at home. We highly recommend this apartment to anyone visiting Pittsburgh.

Mandy’s apartment was beautiful! And comfortable! High quality furniture and kitchen. Easy parking, very quiet, lots of space, and it’s super clean. It’s within walking distance to everything you could need, or it’s easy to use your car if needed. Mandy is very nice. We had no issues, but she checked on us during our stay. I will definitely stay in her home again if I return to Pittsburgh! Highly recommend a stay with her!

Kelly hosted my brother for two months while he was apartment hunting. She was gracious and accommodating. The space is absolutely charming! It’s the top floor of a grand old Victorian house in a safe and very walkable, convenient neighborhood. The room is spacious; the bed is huge and comfortable. The cozy armchair is perfect for reading or watching TV. There is a dining area, kitchenette (no sink) with coffee maker, kettle, toaster oven and hot plate. The bathroom is clean and bright. There’s a large, furnished front porch for relaxing and enjoying the local families walking their dogs! If you’re looking for a homey and unique space, Kelly’s place is for you!

Really lovely AirBnB in an old victorian house. Comfortable beds, great shower, and a friendly host. Well equipped and no issues at all. The neighborhood is great- very walkable/bikeable, playgrounds for kids, lots of good restaurants and fun shops. We’d happily stay here again if we come back to Pittsburgh. Thanks!

Great place, super location with very convenient parking. The location was easy to find and very convenient for the activities for which we visited Pittsburg. The area seems safe and is very quiet. The apartment if compact but has everything needed for a short stay. Great wi-fi and secure access. This listing fitted our needs perfectly and Janine is a great host, responding to any messages from us very quickly and fully. Thoroughly recommend it.

Pleasant stay- very responsive host. The place is suitable for 1 person or a couple to stay. Walkable to Walnut Street and safe neighborhood. Would definitely recommend!

Very clean space. Neighborhood was quiet and we felt very safe at any time of day or night. Bed was very comfortable and towels and linens were very clean and soft.

Susan is an excellent host—very professional, responsive & friendly. Apartment was in great shape & the location was ideal for us being near family in Highland Park. Would definitely return.

My wife and I were in town for the PJ shows. The location was great as were the views. We had no issues with anything. Parking was easily accessible and reasonably priced. It was an easy walk to the Arena. The Speckled Egg was delicious as were many other spots near by. Pittsburgh was a wonderful experience - food, entertainment, walkability, friendliness, and the Lavaugh's spot was a great spot to rest your head at the end of a long day!

This is the third or fourth time we have stayed at Kelly Jane’s in Wilkinsburg, Pittsburgh It is near our daughter, granddaughter and son-in-law’s which is why we chose it to begin with. But we also loved the apartment—2 bedrooms and it is very clean, pretty quiet, and extremely well furnished. It is probably the best equipped rental I have ever seen. Everything you would need is provided. She has thought of everything. She is always responsive in communications and her instructions are clear. My sister stayed with us here for the first time and she thought it was great too. We really enjoyed our stay.

I needed a place last minute for work and this place worked out great!

Felt Instantly at Home Such a great spot! Pre-arrival and day of check-in details were clear and super-helpful. The unit is thoughtfully decorated with all the conveniences one could want and special touches that make it unique. Helpful guides and QR codes are located throughout. The location included a Starbucks downstairs (and a coffee shop across the street called Brother Andre’s that has 5.0 rating) and a well-equipped gym.

We stayed at Kristi's place for two weeks and couldn't have been happier. It was clean and comfortable and had many of the extras that make for an excellent stay: the closets were huge, the kitchen had everything we needed, off-street parking, a water filter, and a nice shower. Kristi was very responsive.

This was my first time in Pittsburgh and wanted to see the city. I couldn't have had a better view than the one I saw from the balcony at Milo's Air B&B and it was a convenient location to the events that I had planned. Checking in and out was simple and Milo was a fantastic host. I would totally recommend this place.

The place is exactly as described. We traveled with our dogs and the space was spacious for all of us. We loved that there is parking in the unit. A little green area is available in the same spot which was convenient for our dogs. We had a question about locking the door and the host was super quick to respond and helpful. I just noticed that the windows were a little bit dirty but other than that, everything was clean!