Vacation rentals in Shadyside, Pittsburgh

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Top-rated vacation rentals in Shadyside, Pittsburgh

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Top guest favorite

A cozy reading nook is presented, featuring wooden walls and two abstract paintings above a shelf. A small bookshelf houses a selection of books, while a wooden chair with a cushion invites relaxation. Natural light filters in through the adjacent window, enhancing the serene setting.

Apartment in East Liberty

4.96 out of 5 average rating, 139 reviews

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.

Guest favorite

A dining area is presented with a polished granite countertop, set with plates and glassware. Natural light streams in through large windows, reflecting in the shiny surface. A subtle arrangement of greenery can be seen in the background, enhancing the inviting ambiance.

Apartment in Shadyside

4.91 out of 5 average rating, 104 reviews

Huge Open Concept 2BR by Walnut

HUGE apartment In the heart of Shadyside w/ room for the whole family! 1 Block to Walnut St & FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 2 floor apt in a prime location, w/ all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, & fitness studios close by. The building was gutted & remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances is brand new!

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, 654 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.

Guest favorite

A spacious bedroom is featured, adorned with a wooden bed frame and a striped blanket. Two bedside lamps sit on white nightstands, and a large window allows natural light to fill the room. A decorative area rug complements the wood flooring beneath.

Apartment in Shadyside

4.91 out of 5 average rating, 132 reviews

Shadyside/Pittsburgh, Modern&Accessible 2BD w/Prkg

Spacious and family oriented, Accessible & Modern 2 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 2 bedrooms & 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

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, 26 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

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 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!

Superhost

A spacious front porch is showcased, featuring a long, low sectional sofa with light-colored cushions. The brick wall is complemented by a house number plaque. Natural light filters through large windows in the background, enhancing the inviting outdoor sitting area.

Apartment in Shadyside

4.82 out of 5 average rating, 276 reviews

Chic & Cozy 2BR | Walkable Shadyside Location

Fresh 2 BR apartment in the heart of Shadyside! Prime location, steps from UPMC Shadyside & Walnut Street! Fully equipped for either a long or short stay! 🌟King Bed (Memory foam mattress) ⭐️Queen Bed (Memory foam mattress) 🌟Pet friendly! ⭐️Central AC/ Heat 🌟Fully stocked & equipped kitchen ⭐️Luxurious waterfall shower head 🌟Two Smart TVs ⭐️Free Street parking 🌟Laundry (Shared & Free) ⭐️Pull out bed (Full) 🔥Message today to secure your reservation!🔥

Guest favorite

Apartment in Shadyside

4.93 out of 5 average rating, 87 reviews

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! 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 IT IS RESERVED IN ADVANCE. 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

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).