
House holiday rentals in Squirrel Hill
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Top-rated house rentals in Squirrel Hill
Guests agree: These houses 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 Squirrel Hill 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

Cheerful 4BR Chalet with Seasonal Pool, Hot Tub

Spacious House w/ Pool @Wexford

PIT Staycation Retreat with Pool House!

Cozy & Beautiful Pittsburgh Home
Weekly house rentals

Entire1932ArtistBungalow4You

King Bed, Artist's Flat

Squirrel Hill Elegant Bright House

Historic Luxury in Highland Park

Avant-Garde Escape by Walnut

Family & Pet-Friendly Home w/ Fenced Yard & Office

Squirrel Hill Gem! Private Garage! Sleeps 10!

Upscale spacious kid-friendly home, amazing views!
Private house rentals

Free Parking | 10 min to Pitt+CMU+hospitals

Soaker Tub, Driveway Parking, King Beds, Elegant!

Huge 4br, rooftop deck, 4 balconies, garage, more!

5 King Bed Family Home | Frick Park | Point Breeze

Private House with Stone Patio and Sun Room

Charming 3BR |Shadyside |2 King + 2 Twin |Walkable

Karen's Place

The Lloyd ´Little Housé
Destinations to explore
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- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Oakmont Country Club
- Ohiopyle State Park
- Idlewild & SoakZone
- Kennywood
- Yellow Creek State Park
- National Aviary
- Raccoon Creek State Park
- Point State Park
- Carnegie Museum of Art
- Fox Chapel Golf Club
- Hidden Valley Resort
- Schenley Park
- Phipps Conservatory and Botanical Gardens
- Carnegie Science Center
- Narcisi Winery
- Bella Terra Vineyards
- Cathedral of Learning
- Oglebay Resort