
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.
Holiday 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

Entire private floor (giant Jacuzzi with shower!)

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

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

House 3bed Free Parking Walk to Bars & Shops

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

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

Cozy + Modern apartment near the city!

Thoughtful, Furnished, Convenient in Squirrel Hill

Squirrel Hill Elegant Bright House

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

Beechwood BNB
Family-friendly home rentals with wifi

Renovated 2BR Great Location - No Cleaning Fee

Lawrenceville modern 1 story

Bright & sunny apt in Shadyside with free parking

Urban Eclectic II, Private Room/Entrance/Bath

Shadyside 2 Bedroom Apartment.

Cozy 1 bedroom in Regent Square

The best place to stay in Pittsburgh by Downtown!

2BR home in very hip neighborhood
Quick stats about holiday rentals that are family-friendly in Shadyside, Pittsburgh
Total rentals
100 properties
Nightly prices starting at
ยฃ38 before taxes and fees
Total number of reviews
7.7K reviews
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
Destinations to explore
- House rentalsย Shadyside
- Rentals with a patioย Shadyside
- Rentals with an EV chargerย Shadyside
- Rentals with a washing machine and dryerย Shadyside
- Family-friendly rentalsย Shadyside
- Rentals with a fireplaceย Shadyside
- Rentals with outdoor seatingย Shadyside
- Pet-friendly rentalsย Shadyside
- Fitness-friendly rentalsย Shadyside
- Flat rentalsย Shadyside
- Family-friendly rentalsย Pittsburgh
- Family-friendly rentalsย Allegheny County
- Family-friendly rentalsย Pennsylvania
- Family-friendly rentalsย United States
- Yurt Rentalsย United States
- Yurt Rentalsย United Kingdom
- Castle Rentalsย United States
- Houseboatsย United States
- Holiday Caravansย United Kingdom
- Private Island Rentalsย United States
- Farm Housesย United States
- Farm Cottagesย United Kingdom
- Cabin Rentalsย Australia
- Luxury Cabinsย United Kingdom
- Luxury Cabinsย United States
- Holiday Chaletsย United Kingdom
- Cottage Rentalsย United States
- Holiday Cottagesย United Kingdom
- Mansion Rentalsย United States
- Villa Rentalsย United Kingdom
- Holiday Bungalowsย United Kingdom
- Bungalow Rentalsย United States
- Condo Rentalsย United States
- Holiday Apartmentsย Australia
- Holiday Housesย United States
- Holiday Housesย United Kingdom
- Private Holiday Rentalsย United Kingdom
- Big House Rentalsย United States
- Big Cottagesย Australia
- Large Villasย United Kingdom
- House Rentals with a Poolย United States
- Cabin Rentals with a Poolย United States
- Villas with a Poolย United Kingdom
- Apartments with a Hot Tubย United States
- Holiday Cottages with a Hot Tubย United Kingdom
- Beach Cabinsย United States
- Beach Condosย United States
- Beachfront Rentalsย United States
- Beach Housesย United Kingdom
- Beach Villasย United Kingdom
- Coastal Cottagesย United Kingdom
- Pet-Friendly Vacation Rentalsย United States
- Pet-Friendly Beach Rentalsย United States
- Pet-Friendly Cabin Rentalsย United States
- Dog-Friendly Cottagesย United Kingdom
- Luxury Dog-Friendly Cottagesย United Kingdom
- PNC Park
- Seven Springs Mountain Resort
- Strip District
- Carnegie Mellon University
- Fallingwater
- Hidden Valley Resort
- Pittsburgh Zoo & PPG Aquarium
- Oakmont Country Club
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Yellow Creek State Park
- Point State Park
- Idlewild & SoakZone
- Oglebay Resort
- National Aviary
- Kennywood
- Schenley Park
- Carnegie Science Center
- Carnegie Museum of Art
- Bella Terra Vineyards
- Raccoon Creek State Park
- Boyce Park Ski Resort
- Children's Museum of Pittsburgh
- Fox Chapel Golf Club