
Family-friendly holiday rentals in Shadyside, Pittsburgh
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shadyside, Pittsburgh
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shadyside, Pittsburgh family-friendly rentals
Family-friendly home rentals with a hot tub

Hot Tub Infrared Sauna Peloton treadmills

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

Luxe Shadyside Victorian★Central★ Park free★8 beds

Oakmont Home with Hot Tub
Family- and pet-friendly home rentals

House 3bed Free Parking Walk to Bars & Shops

Cozy + Modern apartment near the city!

Squirrel Hill Elegant Bright House

Spacious Modern Home • Rooftop Deck

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

Beechwood BNB

View, Off Grandview Drivewy Parking! Mt Washington

Comfortable Mt. Washington Home -min from downtown
Family-friendly home rentals with wifi

Renovated 2BR Great Location - No Cleaning Fee

StudioApt near Oakland,DT,M'ville close to US OPEN

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

Urban Eclectic II, Private Room/Entrance/Bath

Glenshaw Guesthouse

Cozy home in "Little Italy"

Home away from Home in South Side Flats

Beautiful 3BR Home with Cozy Front & Back Porches!
Quick stats about holiday rentals that are family-friendly in Shadyside, Pittsburgh
Total rentals
110 properties
Nightly prices starting at
£37 before taxes and fees
Total number of reviews
8.2K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Wifi availability
100 properties include access to wifi
Destinations to explore
- Rentals with a patio Shadyside
- Family-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Rentals with a washing machine and dryer Shadyside
- Fitness-friendly rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with outdoor seating Shadyside
- House rentals Shadyside
- Rentals with a fireplace Shadyside
- Flat rentals Shadyside
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- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Oakmont Country Club
- Ohiopyle State Park
- Idlewild & SoakZone
- Kennywood
- Yellow Creek State Park
- Raccoon Creek State Park
- National Aviary
- Point State Park
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Hidden Valley Resort
- Phipps Conservatory and Botanical Gardens
- Narcisi Winery
- Schenley Park
- Carnegie Science Center
- Bella Terra Vineyards
- Cathedral of Learning
- Oglebay Resort