
House holiday rentals in Shadyside, Pittsburgh
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Top-rated house rentals in Shadyside, Pittsburgh
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Popular amenities for house rentals in Shadyside, Pittsburgh
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

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden
We had a good stay for grad weekend for my daughter. Enjoyed the place, the nice TV, the many snacks provided and the back garden.

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!

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

Near Hospitals + Great Food, w/ Off-Street Parking
Great location, easy to walk to things and close to several bus stops. The place itself was accurate to the description, clean, and had everything I needed for a two week stay.

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!!

Cozy/Spacious 1BR whole space
Stayed here for over a month, it’s a cozy place for long time stay. Sesan is a great host, easy to communicate and really responsive.

2 beds/1.5 bath Hygge-Hus, Minute to Cafes & Shops
It was wonderful, place is REALLY cute, clean and we felt very safe. We arrived in town a little earlier than we expected, and I called Sofia and we were able to get in two hours before normal check-in time, that was very nice. Sofia also had a fresh and delicious loaf of bread waiting for us (loved it). We will definitely stay there again when and if it is available. Thank you Sofia & Rick Bill and Barb

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!
Private house rentals

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

Luxe Kitchen, Rooftop deck, Garage, Kid Friendly!
This was, by far, the best Airbnb we’ve ever stayed in. We were very impressed by everything, from the communication to the incredible decor at the house (I want them to decorate my actual house - it’s that good lol). Our only regret is not being able to stay longer. 10/10. Highly recommend especially for people with families/larger groups.

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!

Lawrenceville Gem:2 Kings & Yard
Highly recommend staying at this place if you are interested in the Lawrenceville area! It was very walkable to everything we wanted to do in the neighborhood. Parking seemed intimidating at first, but once we did it once it felt very doable. It also helps that Julie has a carport not far away if street parking is unavailable. The space itself is amazing! Very clean, extremely comfortable. Would love to stay again in the future!

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!

Artsy Home in a Great Location!
Great stay and great location. I was a little nervous as to whether parking would be an issue since it is streetside and it wasn't a problem at all - always something out front or next door. if you go down to the Butler Street restaurants, definitely walk there. Parking gets harder the closer you get. Place is exactly as described and we would stay again.

Mid-century modern Lustron & Japanese garden
Perfect house for a solo traveler. Clean, quiet, and equipped with everything you need. The host is very helpful and made the stay easy and comfortable.

Lawrenceville Retreat w/ Parking and Yard
Condo appeared to be recently renovated and was extremely clean. Location was great. Condo is in a quiet neighborhood and close to numerous restaurants, breweries, pubs and even a wine bar. All were within walking distance. Tyler was very responsive to any questions we had and the basket of snacks was a nice touch as well.
Quick stats about house rentals in Shadyside, Pittsburgh
Total rentals
90 properties
Nightly prices starting at
$39 SGD 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
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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