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.

Daniel was responsive and kind! The house was clean and looked just like the pictures!

Alexander’s place was great! We went to a concert at PNC park and was able to walk home. It was perfect!

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!

Jake was an amazing host! It was a great spot for our family of four. He really went above and beyond. We didn’t get in until after midnight on our check in date and they were kind enough to toss a few groceries I had ordered in the refrigerator for us. Very responsive! We used to live in Shadyside so are familiar with the area and it’s such a great spot. Easily walkable to everything but just far enough away to be peaceful and quiet. Great spot for our family to visit.

Great location, easy to walk to things and close to several bus stops. The place itself was accurate to the description, clean, and had everything I needed for a two week stay.

Before even arriving, Julie was very responsive when I had specific questions. We arrived late and she had set up the pack and play, which was much appreciated, as we needed to get our baby down. The place was perfect for a family of four and the beds were very comfortable. We met Julie and her family and they were nothing but welcoming and gracious. We highly recommend!!

This is a must stay. Julie was great. The place is beautiful. If you come to Pittsburgh you’ve to stay here. Everything you need this place has. We will for sure be back. Thank you for everything.

The apartment was just as expected from the pictures. It's nicely decorated, yet clutter free, which we appreciated. Carly was very responsive and helped us get settled in. We had everything we needed for our 4 night stay. We appreciated the extra towels and blankets - they make your stay comfortable. We also used the kitchen while we were there and found everything we needed for simple meals for 2. It was a safe neighborhood, quiet and the space felt private. We paid the $20 and had a parking space at the back of the building for the entire stay. Very convenient! We already booked the space again for our next trip to Pittsburgh.

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.

A nice cozy place, very good neighborhood. Walkable to supermarkets, a short bus from university and parks and restaurants. Bus stand right in front of the apartment. House in a very nice building - lots of good amenities! It's a bit small if you're more than two people. But for two people or two and a kid, it's a great place for the price. Recommend to people wanting to spend a few days in 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!

Justine & Tristan have succeeded in creating a welcoming and comfortable space. Cleverly designed & aesthetically pleasing, well made furniture, a very comfortable mattress, real, well cared for plants, high quality linens & house wares — they have put a lot of thought into this & as a result it feels like home. The location is excellent (parks, great food & coffee, lots of cycling paths). The sound transfer from the street is completely expected for an urban setting, and not disturbing at night. They are extremely responsive, and provided flexibility with both check-in and check-out. We will definitely be back!

Julie’s place was well located, easy to navigate, and beautifully kept. It made seeing Shadyside and Pittsburgh easy

Michelle and her dad, Mike, were great hosts! Their apartment is roomy and well equipped. It was a good fit for a family of three, but I wouldn't recommend it for two couples as there's only one bathroom (with a great shower). It's got plenty of workspace, including a full desk, and the underground parking was easy to access. I'd recommend this apartment highly and would be happy to stay there again. Thanks for a great stay in the 'burgh!

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.

The parking requires a passcard which you have to pickup in a lobby lockbox, and practically speaking you need to do that before you go to your condo. It's a few steps getting in, but they have made it as simple as possible and it is very well documented, so be sure to read all the directions to, and entry steps in, carefully. Once you are in you are going to like how nice and clean it is and how they have thought of everything. Enjoy Pittsburgh! Its a great city with awesome food and great people.

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!

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.