Family-friendly holiday rentals in Wilkinsburg

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wilkinsburg family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Squirrel Hill North
4.87 out of 5 average rating, 104 reviews

Hot Tub Infrared Sauna Peloton treadmills

AmyRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Shadyside
5 out of 5 average rating, 21 reviews

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

MaraRating, 5 stars1 month ago
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.
Top guest favourite
Home in Shadyside
5 out of 5 average rating, 23 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

GillianRating, 5 stars1 month ago
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!
Top guest favourite
Bungalow in Oakmont
4.99 out of 5 average rating, 74 reviews

Oakmont Home with Hot Tub

KevinRating, 5 stars2 months 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 South Side Flats
4.87 out of 5 average rating, 45 reviews

House 3bed Free Parking Walk to Bars & Shops

BrandyRating, 5 stars3 weeks ago
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!!!!
Top guest favourite
Flat in Pittsburgh
4.95 out of 5 average rating, 279 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

JenniferRating, 5 stars2 weeks ago
This was the second time we stayed at Tyler's place and it was just as nice as the first time. The apartment is close to my daughters house which makes it convenient, very clean and the pictures and description on Airbnb are accurate. Close to public transportation for Pittsburgh's sites.
Guest favourite
Home in Squirrel Hill South
4.76 out of 5 average rating, 50 reviews

Squirrel Hill Elegant Bright House

AaronRating, 5 stars1 week ago
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.
Guest favourite
Home in Cranberry Township
4.77 out of 5 average rating, 133 reviews

Wonderful home in quiet neighbourhood

ScottRating, 5 stars3 weeks ago
Karen's house was a great place for our short family visit to the Pittsburgh area. The house was very clean, the kitchen is set up nicely and has plenty of cooking utensils, pans and plates/silverware. The backyard is large and is fenced in which was great for our dogs. The deck is also large with a table and chairs - if the weather was nice, it would have been a great place to sit and relax. Overall, we enjoyed our stay here and would stay here again.
Top guest favourite
Home in South Side Flats
4.97 out of 5 average rating, 342 reviews

Spacious Modern Home • Rooftop Deck

SeanRating, 5 stars3 weeks ago
Great place. Very close to the bars and restaurants. Had a great time
Superhost
Flat in Mount Washington
4.87 out of 5 average rating, 462 reviews

View, Off Grandview Drivewy Parking! Mt Washington

JillRating, 5 stars2 weeks ago
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.
Superhost
Home in Bloomfield
4.65 out of 5 average rating, 246 reviews

👑King Bed⚡ Quiet ‧ West Penn🏥 Parking 🐶Pets

AndersonRating, 5 stars2 months ago
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.
Top guest favourite
Cabin in Pittsburgh
4.93 out of 5 average rating, 159 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

WilliamRating, 5 stars2 weeks ago
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.

Family-friendly home rentals with wifi

Guest favourite
Apartment in Shadyside
4.98 out of 5 average rating, 43 reviews

Bright & sunny apt in Shadyside with free parking

EllenRating, 5 stars1 month ago
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!
Guest favourite
Flat in Bloomfield
4.82 out of 5 average rating, 148 reviews

Off St. Parking | No Steps | Walk to Liberty Ave

DavidRating, 5 stars1 week ago
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.
Guest favourite
Guest house in Mexican War Streets
4.99 out of 5 average rating, 98 reviews

Urban Eclectic II, Private Room/Entrance/Bath

DiannRating, 5 stars6 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 favourite
Home in Bellevue
4.99 out of 5 average rating, 87 reviews

Grand on Grant

CharlesRating, 5 stars3 weeks ago
Great place. This is the place we will get whenever we come back to the area.
Top guest favourite
Home in Natrona Heights
4.98 out of 5 average rating, 83 reviews

Historic Farmhouse north of Pittsburgh

JohnathanRating, 5 stars6 months ago
We've stayed at the farmhouse several times and each visit is better than the last. The home is always cozy and welcoming, and Christy is very responsive and accommodating. Recent upgrades to the property such as a turnaround in the driveway and a firepit make the experience even better. Can't wait to stay again!
Guest favourite
Home in Pittsburgh
4.93 out of 5 average rating, 43 reviews

5-BR Home (Sleeps 10) Close to Oakmont/Downtown

MichaelRating, 5 stars8 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
Flat in Squirrel Hill South
4.78 out of 5 average rating, 144 reviews

Beechwood BNB

WillRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Pittsburgh
4.94 out of 5 average rating, 95 reviews

Location-Location-Location in LEBO!

MargaretRating, 5 stars6 months ago
Leslie has a beautiful home, a true Mount Lebanon gem with gorgeous details and modern amenities. The living area was comfortable, the kitchen well stocked, and she left very helpful notes. We love the neighborhood- lots of shops and restaurants in walking distance and yet the street was quiet and safe. Highly recommend!

Quick stats about holiday rentals that are family-friendly in Wilkinsburg

  • Total rentals

    30 properties

  • Nightly prices starting at

    $26 SGD before taxes and fees

  • Total number of reviews

    1K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore