Holiday rentals in Shadyside, Pittsburgh

Sunny Shadyside Condo with Private Garage

Peaceful and unique 2 bedroom, 2 bathroom loft style condo with sauna, soaking tub, private patio and garage. Located in Pittsburgh's iconic Shadyside neighborhood - just steps from Walnut Street, and some of Pittsburgh's best shopping and dining options. An 8 minute walk to UPMC Shadyside, and a 20 minute walk to Carnegie Mellon University, Bloomfield, and Friendship. Direct airport bus stops 3 blocks from house. Due to the layout of the condo, the space is not ideal for small children.

Sunny Spacious Shadyside 1 bedroom

Bright one bedroom apartment can sleep up to three.Centrally located and just steps from Shadyside Hospital.The apartment offers guests easy access to numerous attractions, museums, stadiums, and concert venues.Just a few minutes walk to bars, restaurants, grocery stores, and shopping.This quaint apartment is perfect for a short or long term stay.Designated parking space makes it easy for you to come and go as you please.Fully equipped kitchen.Public transportation and rentable bikes close by.

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

The Bloomfield Nook

This charming, remodeled 1st-floor rental in Bloomfield blends historic character with modern upgrades. It features new floors, fresh paint, an updated kitchen with new appliances, and a renovated bathroom. Furnished with all-new furniture, it also offers a cozy outdoor space and a spacious backyard—perfect for relaxing. Just steps from Liberty Avenue, you'll have easy access to restaurants, cafes, and shops, with nearby transit and neighborhoods like Shadyside and Lawrenceville.

King Bed Comfort | Free Parking | UPMC, Pitt & CMU

✨ Welcome to our stylish and modern studio apartment in the heart of Shadyside! This fully furnished suite features sleek décor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: 🔹 Fitness Center & Yoga Studio 🔹 Free Street Parking 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Retail 🔹 Bike Storage

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

#6 - Lovely one bedroom in the heart of Shadyside

Welcome to Shadyside STAY! This lovely 1 bedroom apartment is located in the ideal central location of Shadyside, situated right on 5th Ave and Ivy Street. It’s only 5 short blocks to grab your favorite coffee or shop at Lululemon or Apple store on Walnut St. In close proximity to CMU, PITT, and UPMC Shadyside making it an ideal place for students, professors, and traveling nurses. CMU’s free shuttle stop is in front of the building, or you can walk to CMU and PITT campus.

Shadyside apartments: 1 Bed-1 full BA Jewel!

Shadyside jewel! Spacious, stylish-&- chic! Conveniently located in the prime of Pittsburgh's favorite walkable neighborhood. Extraordinary comfortable interior with in-suite laundry & exclusive covered front porch! Eat-in or dine out. There are many near-by restaurants, quaint shops, unique restaurants & bars, beautiful city parks, culture-rich museums, state-of-the-art sports facilities, Universities, Hospitals. Super easy access to public transportation too!

NEW * Apt A Bloomfield/Shadyside & free parking

Ground floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield and trendy Shadyside. The apartment was recently updated and feels fresh, spacious. This first floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. Walking distance from UPMC Shadyside (500 ft), Hillman Cancer Center (3 houses down), West Penn Hospital (10 minutes walk, 0.4 mile), within CMU & Pitt shuttle route.