Kid-friendly holiday rentals in Squirrel Hill

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!

We enjoyed staying at Andi‘s place very much. Andi was very responsive and very proactive. If we had a question an issue whatever she took care of it right away. I would stay at Andy‘s place again if need be. Andi was great and went above and beyond

This place is exactly how it’s pictured. Very beautiful and spacious interior with everything you need to be comfortable. The open shower was refreshing. The open concept gave plenty of space and was very well designed. Loved this place and will definitely book again!

Great location and our son loved seeing air hockey for the first time! Nicole patiently helped me figure out how to turn it on. kitchen cabinets are well labeled and shower had nice hot water. We walked to blue slide playground. Make sure you are comfortable carrying your luggage up stairs to stay here, not a problem for us.

Yuliya’s place was nice and clean and had everything we needed for our stay in Pittsburgh. She was very easy to communicate with and answered any questions we had quickly.

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.

Maggie’s place is a great find. We spent three days here and we absolutely loved the house. The overall feel but also all the nice details and charming touches. The place looks just as great as in the photos. The neighborhood has lots to do and see but it’s also surprisingly quiet and peaceful. We also really enjoyed the elevated terrace out back. Maggie is a great host. She gave us all the information we needed at all times and she’s super friendly. Everything was perfect, this is a great find.

The place was great! My daughter and I came to Pittsburgh for a concert at the Steelers Stadium. It was less than 25 minutes from the stadium. The only thing that kind of got me was nothing Shadina could control. That is the 1st morning my car smelled like weed. But other than that we really enjoyed our stay there. Thank you Shadina!

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!

The apartment was very comfortable for two people. We were close to Southside Works and there were many restaurants and coffee shops within walking distance. We took a lovely 3-mile walk along the trail that runs along the river. We were in town for a concert at PPG Arena, and it was easy to Uber back and forth.

My spouse and I stayed at Mariam’s place from May 15-23 and it was exactly what we needed… cozy, cute, and tucked into a quiet residential area. The homey feeling we got just from seeing it on Airbnb remained throughout stay. That vibe, along with her great reviews, is why we chose it. The bathroom was thoughtfully stocked with facial pads, cotton balls, Q-tips, bath bombs, and shower steamers on top of the expected bath linens. The tub was a major draw for us, and it was clear guests are encouraged to enjoy it. The kitchen had a Keurig and pods, basic seasonings, and all the essentials for eating in. A few minor things: the nonstick cookware was a bit worn, there was some pet hair on the couch, and there weren’t any oven mitts. But those details were small in comparison to everything we loved. We were apartment hunting and needed a solid interim home. This was it. Mariam’s attentiveness and care stood out! I’d absolutely stay in one of her places again and definitely recommend it.

Great place to stay, will definitely be back if I need a place to stay in the area.

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.