Family-friendly vacation rentals in Oakmont

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oakmont family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Squirrel Hill North
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 Highland Park
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 Shadyside
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 Shadyside
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 South Side Flats
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 Shadyside
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 Squirrel Hill South
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 Squirrel Hill South
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 Squirrel Hill South
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
Cottage in Glenshaw
4.94 out of 5 average rating, 430 reviews

Glenshaw Guesthouse

Sunny (Kyung Su)Rating, 5 stars2 weeks ago
Mary Kathryn is a great host. Enjoyed staying at her place and I would recommend it to anyone.
Top guest favorite
Apartment in Pittsburgh
4.92 out of 5 average rating, 429 reviews

Historic Charmer | Spacious | Off Street Parking

AlaneRating, 5 stars6 months ago
Lovely river views and sunsets, very comfortable space in a historic home. Easy access to Pittsburgh attractions and friendly host.
Guest favorite
Home in Squirrel Hill South
4.93 out of 5 average rating, 313 reviews

Upscale Modern 2 BR Apartment

LalitaRating, 5 stars2 weeks ago
Convenient location to Squirrel Hill neighborhood restaurants and bars and close to Carnegie-Mellon University. We appreciated the cream for coffee and sparkling water in the fridge. Very comfortable beds.
Superhost
Apartment in Mount Washington
4.87 out of 5 average rating, 455 reviews

View, Off Grandview Drivewy Parking! Mt Washington

SeanRating, 5 stars2 weeks ago
This is my third time staying here and every time it is absolutely wonderful. The location is perfect, the hosts are so calm and cool, and the space is huge. I would recommend this place to anyone!
Top guest favorite
Home in Bloomfield
4.98 out of 5 average rating, 196 reviews

PBR - Pittsburgh Bloomfield Rowhouse

JeffreyRating, 5 stars3 months ago
Absolutely one of the best Airbnb experiences we’ve had. Jeff and Melissa were very accommodating and have a beautiful home. It was very clean and extremely spacious. The cupcakes they provided- seemingly a small gesture- was a nice touch. We will definitely consider staying there the next time we visit Pittsburgh.
Top guest favorite
Apartment in Coraopolis
4.97 out of 5 average rating, 196 reviews

Moon Professional Living Suite B

RileyRating, 5 stars1 month ago
Great place, with lots to do around. Mark was always quick to respond and was super helpful.
Superhost
Home in Pittsburgh
4.83 out of 5 average rating, 403 reviews

Adorable North Side Carriage House

HannahRating, 5 stars2 weeks ago
Daniel’s place was absolutely perfect for our stay in Pittsburgh! Just close enough to downtown and the strip (about a 5-10 minute drive) while also being quiet and private. We always felt safe, and we had a very restful time when we returned back each night. Daniel was very helpful and communicative, as well. We would most certainly stay here again!
Guest favorite
Home in Pittsburgh
4.97 out of 5 average rating, 180 reviews

Luxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks

ThomasRating, 5 stars2 weeks ago
The house is even nicer than the pictures. Everything inside was luxury. Location is great, 20 minute walk to the stadium and 5 minutes away from a few other bars including a cool German spot. Julie was beyond responsive, she was proactive and a true professional.

Quick stats about vacation rentals that are family-friendly in Oakmont

  • Total rentals

    40 properties

  • Nightly prices starting at

    $70 before taxes and fees

  • Total number of reviews

    530 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore