
House holiday rentals in Squirrel Hill
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Top-rated house rentals in Squirrel Hill
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Popular amenities for Squirrel Hill house rentals
House rentals with a pool

Country Retreat: Indoor Pool/Pickle Ball/Sleeps 12
Our stay at Joe's listing exceeded our expectations. The house and surroundings were clean, beautiful and the pool, poker set and table, basketball, golf, etc. made for an ideal bachelor party location. Joe was extremely responsive and helpful with our questions. Highly recommend this spot and we would definitely stay here again.

A Special Retreat! 5 Bedrooms 8 Beds
Place was so nice for my Bachelorette party! Super spacious and beautiful and had a lot of fun rooms! The pool was also a great addition. Only complaint was that the main family room area was pretty warm, it seemed that the ac unit in there would not work. The host was extremely responsive and even checked in on us our second night! Thanks Brianne!

Billy Boy Retreat - Cohosted by Stacy & Dave
Billy Boy Retreat was perfect! Dave and Stacy made everything effortless—from the smooth check-in to thoughtful touches throughout the home. Every amenity we could possibly need was provided, and the space was both spotless and comfortably spacious. It felt just like staying at a beloved aunt and uncle’s home—warm, welcoming, and easy to settle into. The pool was pristine and perfectly heated for all-day enjoyment, and the rafts and pool toys kept the whole family entertained. In the evenings, the outdoor patio and hot tub were ideal for unwinding. We couldn’t have imagined a better place for our family vacation!

Renovated Cozy Duplex w/pool, Close to downtown
We went to a concert in Pittsburgh and it was not a far drive at all. Everything we wanted to do was super close to us. House was very nice and clean. Had all cooking tools for us to use which came in handy. Beds were clean and comfy. Check in was super easy. Pool water was a little green but no big deal. Overall was a great stay. Would stay again.

Spacious House w/ Pool @Wexford
The location of the house made attending the events we were in the Pittsburgh area for easy. The house was spacious and allowed plenty of room for my children and their families to be together. Though not needed there was easy access to restaurants and stores etc.

PIT Staycation Retreat with Pool House!
If I could give my stay 10 stars, I totally would! I'm a little biased about the location because I grew up probably around 2 min from Larry & Mallory's beautiful home, so I know the area is wonderful, peaceful and quiet!! Super easy to check in! Very clean! They literally thought of everything!! The only steps are the ones to get down to the basement. Very accessible if you have bad knees, or can't do stairs. Bedrooms were clean, comfortable and very inviting. TV in one of three bedrooms, TV in the living room, and a HUGE TV in the basement. Great if you are movie-watchers or tv people. Kitchen has everything you need at hand. The coffee station was amazing! Keurig, French press, whole bean coffee with grinder, creamer, and tea for the tea drinkers! Bathrooms were immaculate, plenty of towels & washcloths. Pool and pool house were stunning! It was like I was staying at a resort! I absolutely would recommend "Robinson Retreats" to everyone & can't wait to go back!

Cozy & Beautiful Pittsburgh Home
Enjoyable weekend and the house suited our needs nicely.

Eastside Urban Rental
Loved the place! It’s everything the described on the post. However, the area that the Airbnb is on, it’s rundown and unsafe. Although I loved the place itself, I probably wouldn’t stay here again based on location. But again, I should have known going into it.
Weekly house rentals

King Bed, Artist's Flat
Always love staying here. Large, clean, updated space in Southside Flats. Joy is a great host

Squirrel Hill Elegant Bright House
Carlos's place was great! There was plenty of room for myself and my family. We loved the decor and would recommend the house to anyone needing a place to stay in the area.

Squirrel Hill Gem! Private Garage! Sleeps 10!
Beautifully decorated and large interior. Three full baths and a garage were quite nice bonuses. Booked at last minutes due to problem at other place we planned to stay. Host was extremely accommodating and responsive. Great location. Definitely recommend this place!!

HUGE Brand New Stylish Home ~ Parking~Theatre
Paul's place was perfect for what we needed. Plenty of space, awesome basement entertainment area, and a kitchen and dining setup perfect for our group. Would stay again.

Carnegie Studio - Priv entrance & parking
This place is exactly how it’s pictured. Very beautiful and spacious interior with everything you need to be comfortable. The open shower was refreshing. The open concept gave plenty of space and was very well designed. Loved this place and will definitely book again!

Cheerful 3-bedroom home with on-street parking
Margaret’s place was like a home away from home. Spotless, beautifully decorated, sunny bedrooms and quiet neighborhood. Had a lovely backyard where we could have our breakfast and chill. I am very demanding when it comes to lodging and could not find anything that was not absolutely great. Would definitely stay again. Thanks Margaret!

Upscale spacious kid-friendly home, amazing views!
Shirly was a host that was communicating before, during and after our stay. I would book this location or any location that she has because of how easy it was to get in and the house had everything we needed

Stylish House near Frick Park
Great location and our son loved seeing air hockey for the first time! Nicole patiently helped me figure out how to turn it on. kitchen cabinets are well labeled and shower had nice hot water. We walked to blue slide playground. Make sure you are comfortable carrying your luggage up stairs to stay here, not a problem for us.
Private house rentals

Luxe 5B/2.5B | Off St. Parking | Family-Friendly
Meredith’s house was an absolutely perfect spot for our family in our long weekend in Pittsburgh. Perfect location in an amazing location with all the amenities you could possibly imagine. Our 3 year old daughter loved the extra toys and books as needed. We come to Pittsburgh yearly, and we WILL be back.

4BD Modern Bauhaus Home | BBQ & Prime Location
Overall, we enjoyed our stay at Daniel’s place. The first floor was larger than we expected, including the kitchen, dining and living room. The kitchen had most everything we needed. The master bath was nicely renovated and the shower was like a room within itself! It was very nice! The king sized mattress in the master bedroom was very comfortable. Upon arrival, there were a couple issues with regards to finding clean linens and a couple other things. However, we reported these issues to Daniel and he was quick to respond, extremely apologetic and making changes to assure a perfect stay for his next guests. We would definitely stay at Daniel’s place again!

All new. Near all PGH activities
The finish on this updated house is very nice and it is a very comfortable space. Ken was a great host and I really enjoyed my stay. Great property

Private House with Stone Patio and Sun Room
Patricia’s place was perfect for us! The location was easy to get to and in a great location! Many restaurants, grocery stores and entertainment near by. The house itself was wonderful. The sunporch was my favorite place. Nice table to sit at and enjoy the outside but being inside. The rest of the house was very quaint. The whole house was very clean. All the rooms were the perfect size for us. Nice bathroom with all the amenities we needed. Very clean and lots of towels. Nice bedroom and living room. Loved the laundry room/lots of room/hangers. Closet had great amount of hangers. Loved the 2 tvs. You can’t go wrong renting this house! Patricha was a great host!

4BR Walkable to UPMC & Pitt + Off-Street Parking
Had a great stay in Pittsburgh. Short Uber ride to downtown areas. We were in town for the US Open so we didn’t get to explore the area much but was perfect for our groups needs. House was very clean and creatively decorated. Would definitely recommend!

Prime 5-Bed: Hot Tub, PITT, CMU, Schenley Park
good clean place and close to the convention center. we shared this place with a couple families and it worked out amazing for us! would definitely stay here again!

Charming, quiet house in Pittsburgh's East End
Cute house and neighborhood. Enjoyed our stay! A couple things would have been very helpful in the kitchen- napkins and small plastic bags. Maybe I missed them? Overall very happy with our stay!

A quiet place with a view
Great location if you're looking for something away from the hustle and bustle of the city. 15 minute drive from downtown, nice neighborhood, pictures look like the home, and amenities are as described.
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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