Vacation rentals in Shadyside, Pittsburgh

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Top-rated vacation rentals in Shadyside, Pittsburgh

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Guest favorite

An open-concept kitchen and dining area is presented with dark cabinetry and light countertops. Modern appliances are visible, along with a breakfast bar with seating. Natural light floods the space through large windows, highlighting the polished wooden floors and the staircase leading to the upper level.

Apartment in Shadyside

5 out of 5 average rating, 8 reviews

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.

Superhost

A view from the entrance showcases a living area with a light brown couch positioned near a dark coffee table. A flat-screen TV is visible on a stand, and a lamp provides illumination. A doorway leads to additional rooms, enhancing the apartment's layout.

Apartment in Shadyside

4.78 out of 5 average rating, 656 reviews

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.

Top guest favorite

The entrance to the sunporch suite is framed by a charming door. Through the door, a spacious area is visible, featuring a bed and a small table. Warm light from lamps enhances the inviting atmosphere, while large windows let in natural light, overlooking the greenery outside.

Guest suite in Highland Park

4.98 out of 5 average rating, 241 reviews

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.

Guest favorite

A grand staircase is displayed, featuring an elegant wooden railing and intricate balusters. Light from a chandelier illuminates the space, highlighting the decorative elements. Artwork is visible on the walls, and a cozy seating area is located at the top of the stairs.

Apartment in Shadyside

4.96 out of 5 average rating, 27 reviews

Renovated 2BD APT in Shadyside

Welcome to Shadyside STAY! We're thrilled to offer you a fully renovated 2-bedroom apartment in the heart of Shadyside, at 5th Ave and Ivy St. Just a short 5-block walk takes you to your favorite coffee shops, Lululemon, or the Apple store on Walnut St. Our prime location near CMU, PITT, and UPMC Shadyside is ideal for students, professors, and traveling nurses. The CMU shuttle stops right outside, and both CMU and PITT campuses are within walking distance. Come visit us at "Shadyside STAY."

Guest favorite

Apartment in Shadyside

4.99 out of 5 average rating, 85 reviews

Betwn Ellsworth & Walnut! Sleeps4! Parking&Laundry

This remodeled apartment is in an ideal location in Shadyside just a short walk to CMU, Pitt, Walnut Street and much more! My apartment features a deck, open-concept layout, bedroom with a walk-in closet, central air, and free laundry. One parking spot is available IF RESERVED IN ADVANCE. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa couch that very conveniently folds down to transform into a queen-sized bed. The spacious deck is great for relaxing.

Guest favorite

The image features a green door adorned with a festive wreath tied with a bright blue and green bow. A sheer white curtain is visible behind the door, and the wall beside the door is painted in a soft blue shade.

Apartment in Shadyside

4.88 out of 5 average rating, 117 reviews

Victorian home 2 bedroom Shadyside

Bright, sunny, spacious 2 bedroom apartment with 1 parking space in the heart of Shadyside. This apartment is in a Victorian home on a quiet street. There is a train that runs below the street I feel it is part of the history and charm of city living. Shopping, restaurants, UPMC hospitals, Universities, museums and cultural activities, within walking distance or public transportation. The unit has been recently updated, beautiful new bathroom and hardwood flooring through out.

Guest favorite

A close-up view of a smart keypad lock is displayed on the door. The keypad features numeric buttons for code entry. A glimpse of the hallway and living space is visible in the background, showcasing the apartment's welcoming entryway.

Apartment in Shadyside

4.89 out of 5 average rating, 168 reviews

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!

Guest favorite

An elegantly designed entryway features a decorative fireplace with a textured surround, complemented by warm wooden flooring. A staircase with white railing ascends to the upper level, while a large abstract artwork adorns one wall, creating a bright and open atmosphere.

Apartment in Shadyside

4.91 out of 5 average rating, 180 reviews

Shadyside/Pittsburgh, Modern & Unique 1BD w/Prkng

Unique 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 & 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.

Top guest favorite

Apartment in Shadyside

4.99 out of 5 average rating, 155 reviews

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.

Guest favorite

A welcoming entrance features double French doors, framed by large windows that allow natural light to enter. A comfortable wicker bench sits on a striped mat, offering a cozy spot for relaxation. The entrance is accented by neutral painted walls and greenery in view.

Apartment in Shadyside

4.83 out of 5 average rating, 136 reviews

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!

Guest favorite

A modern bathroom features neutral tiled walls and floor. A glass shower with a white curtain is positioned to one side, while a sleek vanity with a sink is situated opposite. Soft lighting illuminates the space, creating a clean and functional environment.

Apartment in Bloomfield

4.9 out of 5 average rating, 446 reviews

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).

Top guest favorite

A kitchen cabinet is shown with its doors open. The shelves contain several clear glass tumblers and a blue glass dish, alongside a modern microwave reflecting the kitchen's sleek design.

Apartment in Shadyside

4.97 out of 5 average rating, 125 reviews

Shadyside King Suite w/ Parking!

Stylish 1BR/1 bath apartment with off street parking in the heart of Shadyside, steps to Walnut St -- DESIGNATED OFF STREET PARKING! Short Walk to UPMC & West Penn hospitals, close to CMU & Pitt! The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit, 70inch 4K TV!