Apartment holiday rentals in Shadyside

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Top-rated apartment rentals in Shadyside

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Top guest favourite
The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.
Flat in East Liberty
4.97 out of 5 average rating, 148 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.

Superhost
A living space is presented with a neutral color palette. A couch and chair are arranged around a small coffee table. A dining area with a table and four chairs is visible in the background. Natural light filters through vertical blinds on a nearby window, illuminating the space.
Flat in Shadyside
4.78 out of 5 average rating, 698 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 favourite
Flat in Downtown Pittsburgh
4.95 out of 5 average rating, 110 reviews

Cozy 1BR Minutes from NFL Draft

Welcome to our newly remodeled 1 bedroom apartment, featuring modern furnishings, upscale appliances, and abundant natural light. Just steps from the David L. Lawrence Convention Center (DLCC), it's perfect for business travelers and event-goers. Enjoy nearby attractions like PNC Park, Market Square, and the Cultural District—all within walking distance. Whether you're visiting for business or leisure, our space provides a comfortable and convenient base for your Pittsburgh stay!

Superhost
The living room features a spacious gray sectional sofa positioned near large windows that allow natural light to fill the space. A modern glass coffee table is centered on a soft area rug, while white interior doors provide access to closet space.
Flat in Shadyside
4.89 out of 5 average rating, 214 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 favourite
A bedroom features a wooden bed with a neatly arranged striped comforter. Neutral-toned artwork adorns the wall above the bed. Soft lighting from a bedside lamp provides illumination, and a doorway leads to a bright, airy space beyond.
Flat in Shadyside
4.92 out of 5 average rating, 158 reviews

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg

Stylish 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 favourite
A modern living area features a light grey sectional sofa draped with a vibrant orange throw. Colorful artwork adorns the wall above a sleek television, while a spiral staircase provides access to the upper levels. A dining area with pink chairs is visible in the background.
Flat in Shadyside
4.99 out of 5 average rating, 160 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.

Top guest favourite
A modern kitchen area features sleek cabinetry alongside a wooden countertop and stainless-steel appliances. A spacious gray sofa with decorative pillows is situated nearby, providing a comfortable seating option. Light streams through a window, illuminating the tiled floor and brick accent wall.
Flat in Friendship
4.9 out of 5 average rating, 484 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 favourite
The living area features a large flat-screen TV mounted on a light wood media cabinet. A round black coffee table is centered on a textured gray area rug. Two windows provide natural light, and framed artwork is displayed on the wall.
Flat in Lower Lawrenceville
4.96 out of 5 average rating, 168 reviews

Off Street Parking, King Bed, on Butler Street!

Free off-street parking right on Butler Street? Check! Welcome to your home away from home, located on arguably the hippest street in Pittsburgh. 20+ bars & restaurants, 3 breweries, and more within three blocks - an active traveler's dream! If you would rather stay in, we have a great work from home space with two desks in separate rooms (perfect for traveling couples), a well stocked kitchen, two smart 4K TVs, comfy couch, and more!

Top guest favourite
Flat in Highland Park
4.99 out of 5 average rating, 124 reviews

Highland Park Carriage House

This two-room apartment is located in the popular East End of Pittsburgh in the Highland Park neighborhood. Highland Park is mostly residential, with a small business district with several popular restaurants, a coffee shop, a bakery, and a small market. The apartment is one block from the bus line, and less than a mile to Whole Foods and an ever growing choice of restaurants in East Liberty. Downtown Pittsburgh is only 4 miles away.

Top guest favourite
A grand three-story building is depicted, showcasing a mix of architectural styles. The structure features pointed roofs, multiple windows, and decorative elements. Lush greenery surrounds the property, while a vehicle is parked in front, indicating the availability of off-street parking.
Flat in Bloomfield
4.92 out of 5 average rating, 258 reviews

Cozy Entire Apt 3 *Friendship Park *free parking

Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. The apartment was recently updated and feels fresh, spacious and eclectic flair. This 3rd floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

Top guest favourite
The open-concept living area features a modern sectional sofa facing a glass coffee table. Brightly lit by natural light, the kitchen showcases high-end appliances, and a dining table is set for four. Wood flooring complements the soft color palette throughout the room.
Flat in Friendship
4.95 out of 5 average rating, 103 reviews

Spacious KingSuite by WholeFoods

Spacious 1 bedroom apartment in a brand new building just a 1 min walk to the new Whole Foods! Short Walk to UPMC, West Penn, & Children's hospitals, close to CMU & Pitt, and Shadyside The building was gutted and entirely remodeled in March 2024, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit

Superhost
A bright studio unit features a tufted queen bed with a patterned duvet, flanked by two nightstands with lamps. A small seating area contains a couch and a coffee table. Natural light enters through large windows, reflecting off the warm wooden floor.
Flat in Bloomfield
4.78 out of 5 average rating, 586 reviews

Apt 2 Lawrenceville studio

Our place is close to nightlife, public transport, the city center, and parks. Kick back and relax in this fully furnished apartment, smart HDTV, fully-equipped kitchent, free wifi, cable, bike rental right across the street. You would love the location, the coziness. place is good for couples, solo adventurers, business travelers, and families (with kids).

Popular amenities for Shadyside apartment rentals

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Quick stats about flat rentals in Shadyside

  • Total holiday rentals

    Explore 190 holiday rentals in Shadyside

  • Nightly prices starting at

    Shadyside holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 22,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    190 of Shadyside holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shadyside rentals

  • 4.9 Average rating

    Shadyside stays are highly rated by guests – averaging 4.9 out of 5!

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