Family-friendly vacation 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
Home in Squirrel Hill North
4.89 out of 5 average rating, 94 reviewsGreen Sunny Bunny Eco Luxe Art & Wellness House
Home in Shadyside
5 out of 5 average rating, 17 reviewsLuxe Shadyside Spa + Parking + 6 Beds + Zen Garden
Home in Shadyside
5 out of 5 average rating, 23 reviewsLuxe Shadyside Victorian★Central★ Park free★8 beds
Bungalow in Oakmont
4.96 out of 5 average rating, 57 reviewsOakmont home with private hot tub
Bungalow in Oakmont
4.99 out of 5 average rating, 71 reviewsOakmont Home with Hot Tub
Family- and pet-friendly home rentals
Rental unit in Pittsburgh
4.7 out of 5 average rating, 67 reviewsGorgeous and large 2 bedroom apt./home near city
Home in South Side Flats
4.89 out of 5 average rating, 35 reviewsHouse 3bed Free Parking Walk to Bars & Shops
Home in Shadyside
4.9 out of 5 average rating, 153 reviewsShadyside 5th Avenue Bedroom, Pvt. Bath, Pkg.
Rental unit in Pittsburgh
4.87 out of 5 average rating, 293 reviewsCozy + Modern apartment near the city!
Home in Squirrel Hill South
4.76 out of 5 average rating, 46 reviewsSquirrel Hill Elegant Bright House
Home in South Side Flats
4.97 out of 5 average rating, 330 reviewsSpacious Modern Home • Rooftop Deck
Home in PITTSBURGH
4.93 out of 5 average rating, 43 reviewsLarge Home Close to Everything in Pittsburgh
Rental unit in Squirrel Hill South
4.77 out of 5 average rating, 135 reviewsBeechwood BNB
Family-friendly home rentals with Wifi
Rental unit in Pittsburgh
4.88 out of 5 average rating, 24 reviewsLarge Studio Apt - Perfect if you're on a budget!
Loft in Troy Hill
4.81 out of 5 average rating, 157 reviewsArtsy Loft Studio 1.1Mi To Downtown
Rental unit in Bloomfield
4.82 out of 5 average rating, 145 reviewsSpacious getaway in Little Italy with Parking
Guesthouse in Mexican War Streets
4.99 out of 5 average rating, 95 reviewsUrban Eclectic II, Private Room/Entrance/Bath
Home in Bellevue
4.99 out of 5 average rating, 75 reviewsGrand on Grant
Rental unit in Pittsburgh
4.95 out of 5 average rating, 92 reviewsCozy 1 bedroom in Regent Square
Rental unit in Squirrel Hill South
5 out of 5 average rating, 55 reviewsThoughtful, Furnished, Convenient in Squirrel Hill
Dome in Pittsburgh
4.58 out of 5 average rating, 40 reviews*Dome Sweet Dome!* Up to 4 guests
Quick stats about vacation rentals that are family-friendly in Shadyside, Pittsburgh
Total rentals
100 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
6.7K 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
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