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 Pittsburgh
4.91 out of 5 average rating, 143 reviewsMy Favorite Sunny Bunny Eco Luxe Stay (Blue)
Jun 30 – Jul 7
Bungalow in Oakmont
4.98 out of 5 average rating, 64 reviewsOakmont Home with Hot Tub
Oct 21 – 28
Home in Pittsburgh
5.0 out of 5 average rating, 10 reviewsLuxe Shadyside Spa + Parking + 5 Beds + Zen Garden
Feb 14 – 21
Bungalow in Oakmont
4.96 out of 5 average rating, 53 reviewsOakmont home with private hot tub
Oct 20 – 27
Home in Pittsburgh
4.88 out of 5 average rating, 74 reviewsSunny Bunny Eco Luxe Art & Wellness House (Green)
Dec 28 – Jan 4
Home in Pittsburgh
5.0 out of 5 average rating, 18 reviewsLuxe Shadyside Victorian★Central★ Park free★8 beds
Jan 15 – 22
Family- and pet-friendly home rentals
Apartment in Pittsburgh
4.87 out of 5 average rating, 281 reviewsCozy + Modern apartment near the city!
May 28 – Jun 4
Apartment in Pittsburgh
4.95 out of 5 average rating, 242 reviewsThe Pittsburgh Suite *Free Parking, 10mins-DWNTWN
Aug 10 – 17
Cabin in Pittsburgh
4.92 out of 5 average rating, 127 reviewsCabin in Pittsburgh. 20 minutes to Pittsburgh
Nov 28 – Dec 5
Home in Monroeville
4.84 out of 5 average rating, 141 reviewsMayberry Escape
Apr 10 – 17
Townhouse in Pittsburgh
4.93 out of 5 average rating, 320 reviewsCharming Home • Vibrant Neighborhood
Aug 26 – Sep 2
Home in Pittsburgh
5.0 out of 5 average rating, 209 reviewsHigh-End South Side 4 Bedroom House, sleeps 15!
Aug 28 – Sep 4
Home in Pittsburgh
4.91 out of 5 average rating, 11 reviewsHouse 3bed Free Parking Walk to Bars & Shops
Oct 20 – 27
Home in Pittsburgh
4.65 out of 5 average rating, 225 reviews👑King Bed⚡ Quiet ‧ West Penn🏥 Parking 🐶Pets
Nov 6 – 13
Family-friendly home rentals with Wifi
Home in Pittsburgh
4.97 out of 5 average rating, 154 reviewsLuxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks
Mar 21 – 28
Townhouse in Pittsburgh
4.81 out of 5 average rating, 181 reviews2BR home in very hip neighborhood
Dec 25 – Jan 1
Apartment in Pittsburgh
4.92 out of 5 average rating, 410 reviewsHistoric Charmer | Spacious | Off Street Parking
Aug 21 – 28
Apartment in Pittsburgh
4.86 out of 5 average rating, 646 reviewsSouth Side Flats - Central to everything!
Feb 20 – 27
Home in Pittsburgh
4.98 out of 5 average rating, 156 reviewsSpacious, attractive apartment in residential home
Oct 7 – 14
Home in Munhall
4.8 out of 5 average rating, 218 reviewsBeautiful 3 Bedroom Home Cozy Front and Back Porch
Jan 13 – 20
Home in Pittsburgh
4.82 out of 5 average rating, 129 reviewsNew remodeled Modern 2BR suite for 4
May 21 – 28
Apartment in Pittsburgh
4.97 out of 5 average rating, 386 reviewsCozy City Getaway*Self Checkin*Safe*Spotless*Stay!
Oct 13 – 20
Quick stats about vacation 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
$50 before taxes and fees
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Deep Creek Lake
- Family-friendly rentals Pittsburgh
- Family-friendly rentals Pittsburgh
- Family-friendly rentals Pennsylvania
- Fitness-friendly rentals Shadyside
- Rentals with a washer and dryer Shadyside
- Rentals with a fireplace Shadyside
- Apartment rentals Shadyside
- House rentals Shadyside
- Rentals with outdoor seating Shadyside
- Monthly Rentals Shadyside
- Rentals with a patio Shadyside
- Pet-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Family-friendly rentals Downtown
- Family-friendly rentals Allegheny County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes