Vacation rentals in Shadyside

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

Shadyside Charm: Cozy Row Home Near Walnut Street

Beautifully maintained Shadyside row home, one block from Walnut Street, with bright open living spaces, updated appliances, and plenty of natural light. Walk to boutiques, cafes, and restaurants. Minutes to CMU, Pitt, and UPMC, with easy public transit access—ideal for campus visits, hospital stays, or weekend trips. Enjoy two off-street parking spots, a covered front porch, and a private deck. Finished basement features a 90” TV plus flexible space for an office, playroom, or cozy movie room.

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.

Shadyside/Central @1 Spacious & Modern 1Bdr w/Prkg

Spacious and family oriented & Modern 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 bedroom, living room & dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

Huge King Suite Just off Walnut

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, CMU & Pitt! HUGE 2 Floor 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

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!

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

This Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, a new sleeper sofa, a full kitchen and a full bathroom with a private entrance on the 2rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

CITY Apt/Free parking/Near West Penn Hosp/CMU/PITT

Enjoy a stylish first-floor 1BR with a gourmet kitchen featuring high-end appliances and a spacious living area perfect for relaxing or entertaining. The queen-size bedroom offers a comfortable night’s sleep. High-speed WiFi and a dedicated workspace make it ideal for business travelers or remote work. Access to the private parking lot. Located near West Penn Hospital and UPMC Shadyside, perfect for couples, visiting families, or medical stays.

Spacious, warm, private apartment near CMU /Pitt

Spacious, warm, private apartment with parking set in a beautiful, quiet, family neighborhood. Just minutes away walking from CMU (10 Min) and Pitt 20 Min). And a 4 minute walk Bus stop (61xx) to all of Pittsburgh. Shadyside, Squirrel Hill and the Carnegie museums are in the immediate neighborhood with great options for dining and entertainment. Also the Phipps Conservatory and Botanical Gardens are only 1.3 Miles from the house.

StudioApt W/Gym+eV+Free Parking+Near Pitt Uni UPMC

Welcome to our stunning cozy 1-bed studio unit. Perfect for both business and leisure travelers, this elegant retreat offers a perfect blend of comfort, style, and convenience, ensuring a memorable stay in the heart of Pittsburgh. Nestled in a prime location, our unit provides easy access to the city’s top attractions, making it the ideal base for exploring everything Pittsburgh has to offer *ID and Background verification needed*