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
Home in Pittsburgh
4.91 out of 5 average rating, 144 reviewsMy Favorite Sunny Bunny Eco Luxe Stay (Blue)
Bungalow in Oakmont
4.98 out of 5 average rating, 64 reviewsOakmont Home with Hot Tub
Home in Pittsburgh
5.0 out of 5 average rating, 12 reviewsLuxe Shadyside Spa + Parking + 5 Beds + Zen Garden
Bungalow in Oakmont
4.96 out of 5 average rating, 54 reviewsOakmont home with private hot tub
Home in Squirrel Hill North
4.87 out of 5 average rating, 75 reviewsSunny Bunny Eco Luxe Art & Wellness House (Green)
Home in Pittsburgh
5.0 out of 5 average rating, 19 reviewsLuxe Shadyside Victorian★Central★ Park free★8 beds
Family- and pet-friendly home rentals
Flat in Pittsburgh
4.87 out of 5 average rating, 282 reviewsCozy + Modern apartment near the city!
Cabin in Pittsburgh
4.92 out of 5 average rating, 129 reviewsCabin in Pittsburgh. 20 minutes to Pittsburgh
Home in Monroeville
4.85 out of 5 average rating, 144 reviewsMayberry Escape
Home in Pittsburgh
4.97 out of 5 average rating, 314 reviewsSpacious Modern Home • Rooftop Deck
Home in Pittsburgh
5.0 out of 5 average rating, 210 reviewsHigh-End South Side 4 Bedroom House, sleeps 15!
Home in Pittsburgh
4.93 out of 5 average rating, 14 reviewsHouse 3bed Free Parking Walk to Bars & Shops
Home in Pittsburgh
4.65 out of 5 average rating, 226 reviews👑King Bed⚡ Quiet ‧ West Penn🏥 Parking 🐶Pets
Townhouse in Pittsburgh
4.75 out of 5 average rating, 306 reviewsRooftop Tranquility! 2-Car Garage! Sleeps 2-12!
Family-friendly home rentals with wifi
Townhouse in Pittsburgh
4.81 out of 5 average rating, 183 reviews2BR home in very hip neighborhood
Flat in Pittsburgh
4.97 out of 5 average rating, 311 reviewsApartment: Home Sweet Home
Flat in Pittsburgh
4.92 out of 5 average rating, 411 reviewsHistoric Charmer | Spacious | Off Street Parking
Guest suite in Pittsburgh
4.64 out of 5 average rating, 155 reviewsLovely Wightman entire suite in Squirrel Hill
Flat in Coraopolis
4.97 out of 5 average rating, 182 reviewsMoon Professional Living Suite B
Flat in Pittsburgh
4.83 out of 5 average rating, 492 reviewsRenovated top floor unit! Close to downtown!
Home in Pittsburgh
4.97 out of 5 average rating, 156 reviewsLuxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks
Flat in Mexican War Streets
4.97 out of 5 average rating, 390 reviewsCozy City Getaway*Self Checkin*Safe*Spotless*Stay!
Quick stats about holiday rentals that are family-friendly in Shadyside, Pittsburgh
Total rentals
90 properties
Wifi availability
90 properties include access to wifi
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Total number of reviews
5.1K reviews
Nightly prices starting at
€ 46 before taxes and fees
Destinations to explore
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