House holiday rentals in Shadyside, Pittsburgh

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Popular amenities for house rentals in Shadyside, Pittsburgh

House rentals with a pool

Top guest favourite
Home in Sarver
4.99 out of 5 average rating, 107 reviews

Country Retreat: Indoor Pool/Pickle Ball/Sleeps 12

TedRating, 5 stars3 weeks ago
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.
Home in Beaver
4.81 out of 5 average rating, 37 reviews

A Special Retreat! 5 Bedrooms 8 Beds

EmilyRating, 5 stars1 week ago
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!
Top guest favourite
Home in Slovan
5 out of 5 average rating, 40 reviews

Billy Boy Retreat - Cohosted by Stacy & Dave

MariaRating, 5 stars5 days ago
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!
Home in Beechview
4.76 out of 5 average rating, 71 reviews

Renovated Cozy Duplex w/pool, Close to downtown

IvyRating, 5 stars1 month ago
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.
Guest favourite
Home in Wexford
4.96 out of 5 average rating, 27 reviews

Spacious House w/ Pool @Wexford

LisaRating, 5 stars1 week ago
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.
Top guest favourite
Home in Coraopolis
5 out of 5 average rating, 30 reviews

PIT Staycation Retreat with Pool House!

JenniferRating, 5 stars1 week ago
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!
Home in Pittsburgh
4.8 out of 5 average rating, 10 reviews

Cozy & Beautiful Pittsburgh Home

TamaraRating, 5 stars6 months ago
Enjoyable weekend and the house suited our needs nicely.
Home in Highland Park
4.73 out of 5 average rating, 90 reviews

Eastside Urban Rental

MariaRating, 5 stars7 months ago
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

Top guest favourite
Home in Shadyside
5 out of 5 average rating, 21 reviews

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

MaraRating, 5 stars1 month ago
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.
Guest favourite
Home in Bloomfield
4.94 out of 5 average rating, 17 reviews

4BD Modern Bauhaus Home | BBQ & Prime Location

JohnRating, 5 stars1 week ago
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!
Guest favourite
Home in South Side Flats
4.93 out of 5 average rating, 61 reviews

King Bed, Artist's Flat

StewartRating, 5 stars3 weeks ago
Always love staying here. Large, clean, updated space in Southside Flats. Joy is a great host
Guest favourite
Home in Bloomfield
4.91 out of 5 average rating, 64 reviews

Near Hospitals + Great Food, w/ Off-Street Parking

BillyRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Squirrel Hill North
5 out of 5 average rating, 25 reviews

Squirrel Hill Gem! Private Garage! Sleeps 10!

ElizabethRating, 5 stars1 month ago
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!!
Guest favourite
Home in East Liberty
4.89 out of 5 average rating, 9 reviews

Cozy/Spacious 1BR whole space

YiwenRating, 5 stars6 months ago
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.
Top guest favourite
Home in Pittsburgh
5 out of 5 average rating, 37 reviews

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

BillRating, 5 stars1 week ago
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
Superhost
Home in Pittsburgh
5 out of 5 average rating, 3 reviews

Carnegie Studio - Priv entrance & parking

ChenelleRating, 5 stars3 weeks ago
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

Top guest favourite
Home in Clairton
5 out of 5 average rating, 50 reviews

All new. Near all PGH activities

WilliamRating, 5 stars6 days ago
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
Top guest favourite
Home in Pittsburgh
5 out of 5 average rating, 16 reviews

Luxe Kitchen, Rooftop deck, Garage, Kid Friendly!

ClaribelRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Pittsburgh
5 out of 5 average rating, 26 reviews

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

KaylaRating, 5 stars3 days ago
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!
Guest favourite
Home in Pittsburgh
5 out of 5 average rating, 24 reviews

Lawrenceville Gem:2 Kings & Yard

StephanieRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Greenfield
5 out of 5 average rating, 80 reviews

Cheerful 3-bedroom home with on-street parking

ParaskeviRating, 5 stars1 month ago
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!
Guest favourite
Home in Bloomfield
4.95 out of 5 average rating, 92 reviews

Artsy Home in a Great Location!

J. RobRating, 5 stars2 weeks ago
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.
Top guest favourite
Home in Squirrel Hill South
4.98 out of 5 average rating, 46 reviews

Mid-century modern Lustron & Japanese garden

MattiasRating, 5 stars6 days ago
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.
Top guest favourite
Home in Pittsburgh
5 out of 5 average rating, 22 reviews

Lawrenceville Retreat w/ Parking and Yard

RobertRating, 5 stars6 days ago
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

Destinations to explore

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  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Pittsburgh
  6. Shadyside
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