Family-friendly vacation rentals in Squirrel Hill

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Squirrel Hill family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Pittsburgh
4.9 out of 5 average rating, 100 reviews

ECO-Luxe Art & Wellness House Green

BradRating, 5 stars2 weeks ago
Andi was great. Very helpful if we had any questions. Place was in great shape and super clean, top to bottom.
Superhost
Guest suite in Pittsburgh
4.85 out of 5 average rating, 224 reviews

Entire private floor (giant Jacuzzi with shower!)

ReneeRating, 5 stars2 weeks ago
This was my very first time getting a Bnb looking forward to booking more hoping they are as great as a host as Devin was he made sure I comfortable and always checked in to see if we needed anything. I will be booking this place in the future if you’re interested in a comfortable space this is the one! Thank you again!
Top guest favorite
Home in Pittsburgh
5 out of 5 average rating, 19 reviews

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

MarlaRating, 5 stars3 months ago
Oh my goodness! Rick is so thoughtful! And super communicative! He provided incredibly detailed information about how to access the house and the parking. Additionally, he had so many thoughtful details in the house in the way of snacks and beautiful flowers. And while we didn’t take advantage of the extensive list of restaurants because of being in town for the holidays, it was really nice how much information he provided. It was a great location especially to our family in Squirrel Hill.
Top guest favorite
Home in Pittsburgh
5 out of 5 average rating, 22 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

BrittanyRating, 5 stars7 months ago
Rick was so incredible. He had the sweetest welcome, clear instructions, and just above and beyond. I can’t recommend this space enough! Cute off the main path place but a walkable distance to very cute bars and restaurants which made it perfect balance for my family. This place is immaculate! When I come back to Pittsburgh this is going to be my place!!
Top guest favorite
Bungalow in Oakmont
4.99 out of 5 average rating, 73 reviews

Oakmont Home with Hot Tub

KevinRating, 5 stars1 week ago
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.

Family- and pet-friendly home rentals

Superhost
Home in Pittsburgh
4.87 out of 5 average rating, 38 reviews

House 3bed Free Parking Walk to Bars & Shops

GailRating, 5 stars3 months ago
Ryan's place was fabulous. It was spacious and beautifully designed. We had everything we needed. I highly recommend you book his place.
Home in Pittsburgh
4.9 out of 5 average rating, 155 reviews

Shadyside 5th Avenue Bedroom, Pvt. Bath, Pkg.

CristyRating, 5 stars5 months ago
My husband loved stating at this place. It was perfect for us to travel from Kentucky to Pittsburgh to attend a Steelers game. We would 100% stay there again. This private room with private bathroom is on the first floor of a three story historic home. Elizabeth, who is the nicest person ever, lives with her husband on the upper two floors. The adorable space was super clean and I felt very at home. The mattress was extremely comfortable and the water was hot in the shower. Bring your own cooler and ice, and you are set. 10 out of 10. Thank you Elizabeth!
Top guest favorite
Apartment in Pittsburgh
4.95 out of 5 average rating, 275 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

RhondaRating, 5 stars2 months ago
What a nice little town, first time for us staying in this part of town and we enjoyed it. Walkable neighborhood, we never moved our car all weekend. Walked to the brewery which we highly recommend the owners were super welcoming. We ate dinner at the speak easy while listening to local music. And ubered over to the Roxian theater for a concert. We stayed in the Pittsburgh unit and had everything we needed, the apts was exactly as described. We would definitely stay at Tyler’s place again. Easy street parking, while it’s described as up and coming we feel it’s beyond that and found it to be safe and established.
Guest favorite
Apartment in Pittsburgh
4.87 out of 5 average rating, 303 reviews

Cozy + Modern apartment near the city!

TerriRating, 5 stars2 weeks ago
Jaclyn's place was a great find! It was an easy 30 minute walk to get downtown. It was clean and equipped with everything we needed, including a delicious selection of coffees and teas! Parking was always available in front of the house. We will definitely use Jaclyn's place the next time we're in Pittsburgh!
Top guest favorite
Apartment in Pittsburgh
5 out of 5 average rating, 60 reviews

Thoughtful, Furnished, Convenient in Squirrel Hill

GregRating, 5 stars3 weeks ago
The stay at Mark and Evan's was fantastic! Their place was everything they described it to be! They went above and beyond to provide all of the extras anybody could ever need... from tasty snacks to bathroom necessities to kitchen extras! I highly recommend staying at their place when visiting Pittsburgh! You will not regret it!
Guest favorite
Home in Pittsburgh
4.75 out of 5 average rating, 48 reviews

Squirrel Hill Elegant Bright House

RobynRating, 5 stars5 months ago
Great communication! Loved the house, clean, fun, everything you need! Highly recommend, will definitely stay again! Thank you!
Guest favorite
Home in Pittsburgh
4.93 out of 5 average rating, 43 reviews

5-BR Home Close to Oakmont/Downtown/Lawrenceville

MichaelRating, 5 stars6 months ago
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!
Superhost
Apartment in Pittsburgh
4.78 out of 5 average rating, 141 reviews

Beechwood BNB

RedaRating, 5 stars1 month ago
Rebecca’s place was a very comfortable and spacious living area. We were in and out a lot due to being there for a funeral and had no issues with parking or entering home. Kitchen was well stocked and linens were clean and abundant. We were able to walk to a restaurant and grocery store which was very convenient. It had a wonderful large front porch. Very satisfied overall with our stay!

Family-friendly home rentals with Wifi

Top guest favorite
Home in Pittsburgh
5 out of 5 average rating, 18 reviews

Lawrenceville modern 1 story

ChristopherRating, 5 stars3 months ago
Christopher’s home in Lawrenceville was thoughtfully designed/furnished, and in such an ideal location. It’s only 20-ish minutes to the airport, super close to the Strip District, and right near the main drag of attractions on Butler Street in Lawrenceville. I was a little concerned about street parking, but it honestly never took more than 5-10 minutes at most to find a nearby spot, usually found one right away. Christopher was also very responsive, and was even kind enough to allow me a bit of a later checkout, which was much appreciated. This was a fantastic and comfortable visit - would be thrilled to book again next time I’m in Pittsburgh. Thank you, again, Christopher!
Guest favorite
Condo in Pittsburgh
4.98 out of 5 average rating, 41 reviews

Bright & sunny apt in Shadyside with free parking

AngelaRating, 5 stars5 months ago
My daughter had to be in the Pittsburgh area for two weeks due to a school requirement. Michael met her there at check in, and made sure she had everything she needed. And, he graciously gave her a late check out since her flight didn’t leave until later in the evening. Everything went smoothly, and this mom was happy she was safe, and grateful for Michael and Michelle’s help.
Top guest favorite
Guesthouse in Pittsburgh
4.99 out of 5 average rating, 98 reviews

Urban Eclectic II, Private Room/Entrance/Bath

DiannRating, 5 stars3 months ago
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! 💛
Top guest favorite
Apartment in Pittsburgh
5 out of 5 average rating, 96 reviews

Shadyside 2 Bedroom Apartment.

MargueriteRating, 5 stars2 days ago
We have stayed with Ann and Mike a number of times and love coming back. They are kind, responsive and add wonderful touches - fruit, bagels, yogurt, juice, plants, and (a personal favorite) coffee to go cups - to name a few. They are wonderful hosts and we are glad to have a home away from home when we come to Pittsburgh.
Top guest favorite
Apartment in Pittsburgh
4.95 out of 5 average rating, 92 reviews

Cozy 1 bedroom in Regent Square

MichaelRating, 5 stars7 months ago
This was our third stay at Martha’s Airbnb. Please see our previous reviews for why we give it a five star rating. It will continue to be our destination of choice when we return to Pittsburgh to visit our son’s family living in the Regent Square area.
Home in Pittsburgh
4.86 out of 5 average rating, 215 reviews

The best place to stay in Pittsburgh by Downtown!

JenRating, 5 stars5 months ago
Great location to stay in Mount Washington. Super walkable to restaurants, bars, and the beautiful views of Mt. Washington. Older home but had everything we needed and comfortable beds. Great place to stay.
Townhouse in Pittsburgh
4.82 out of 5 average rating, 200 reviews

2BR home in very hip neighborhood

AllieRating, 5 stars1 week ago
Thank you for a lovely stay in a beautiful home.
Apartment in Pittsburgh
4.95 out of 5 average rating, 202 reviews

Spacious 2BR 1BA: King and Queen Beds

LorettaRating, 5 stars63 months ago
Thanks for a great stay! Matt was so ice and everything was great. It was fortunate that Victoria had 2 working flashlights readily available when power went out for a bit. That was very helpful!

Destinations to explore