
House vacation rentals in Shadyside, Pittsburgh
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Top-rated house rentals in Shadyside, Pittsburgh
Guests agree: these houses 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 house rentals
House rentals with a pool

Country Retreat: Indoor Pool/Pickle Ball/Sleeps 12

A Special Retreat! 5 Bedrooms 8 Beds

Billy Boy Retreat - Cohosted by Stacy & Dave

Renovated Cozy Duplex w/pool, Close to downtown

Spacious House w/ Pool @Wexford

PIT Staycation Retreat with Pool House!

Cozy & Beautiful Pittsburgh Home

Eastside Urban Rental
Weekly house rentals

Luxe 5B/2.5B | Off St. Parking | Family-Friendly

King Bed, Artist's Flat

Avant-Garde Escape by Walnut

Private House with Stone Patio and Sun Room

2 beds/1.5 bath Hygge-Hus, Minute to Cafes & Shops

Cozy/Spacious 1BR whole space

HUGE Brand New Stylish Home ~ Parking~Theatre

Mid-century modern Lustron & Japanese garden
Private house rentals

4BD Modern Bauhaus Home | BBQ & Prime Location

Pet-Friendly Home with BBQ Grill and Free Parking

Squirrel Hill Gem! Private Garage! Sleeps 10!

4BR Walkable to UPMC & Pitt + Off-Street Parking

A Pearl in Pittsburgh's Little Italy with Parking!

Cheerful 3-bedroom home with on-street parking

Panoramic City Views with Roof Deck |Free Parking

Charming, quiet house in Pittsburgh's East End
Quick stats about house rentals in Shadyside, Pittsburgh
Total rentals
90 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- Rentals with a washer and dryer Shadyside
- Rentals with a patio Shadyside
- Pet-friendly rentals Shadyside
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- Rentals with an EV charger Shadyside
- Kid-friendly rentals Shadyside
- Rentals with outdoor seating Shadyside
- Apartment rentals Shadyside
- Rentals with a fireplace Shadyside
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- PNC Park
- Carnegie Mellon University
- Strip District
- Seven Springs Mountain Resort
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Oakmont Country Club
- Idlewild & SoakZone
- Yellow Creek State Park
- National Aviary
- Kennywood
- Raccoon Creek State Park
- Point State Park
- Hidden Valley Resort
- Schenley Park
- Fox Chapel Golf Club
- Ohiopyle State Park
- Carnegie Museum of Art
- Phipps Conservatory and Botanical Gardens
- Carnegie Science Center
- Oglebay Resort
- Bella Terra Vineyards
- Narcisi Winery
- Senator John Heinz History Center