Vacation rentals in Shadyside

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Top-rated vacation rentals in Shadyside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Apartment 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.

Guest favorite
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.
Apartment in Shadyside
4.78 out of 5 average rating, 692 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 floating home is presented from an aerial view, showcasing its unique two-level structure nestled on the calm waters of the Allegheny River. The wrap-around deck and patio doors are visible, enhancing the connection to nature, with lush greenery lining the riverbank.
Houseboat in Blawnox
4.98 out of 5 average rating, 58 reviews

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Top guest favorite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 289 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.

Top guest favorite
An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.
Apartment in Shadyside
4.97 out of 5 average rating, 144 reviews

Cozy 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, 3 min drive to CMU & Pitt! 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!

Guest favorite
A cozy bedroom features a spacious bed draped in a soft, natural-toned coverlet. A vintage mirror and wooden dresser are positioned against a brick wall. Natural light filters through a stained glass window, illuminating plants nearby. A glimpse of the bathroom is visible in the background.
Apartment in Shadyside
4.91 out of 5 average rating, 11 reviews

A Home In The Heart of Shadyside

Cozy 1 bedroom home steps from Walnut St. It's a little bit rough and a little bit refined (it's our latest work in progress). Its our home and we travel a lot, so we love to share our space with others. Walker's paradise; and very bike-able, with city bikes a block away. AC and heating. * Quiet, safe, and beautiful tree-lined streets * Carnegie Mellon University and East liberty- 6 min by bicycle * University of Pittsburgh - 9 min by bicycle * Shared courtyard and front porch

Guest favorite
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.
Apartment in Shadyside
4.9 out of 5 average rating, 207 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
The spacious bedroom features a wooden platform bed with a plush mattress and white linens, complemented by a decorative blanket. A minimalist bedside table holds a lamp, while two framed botanical prints adorn the wall. Natural light filters through the window, enhancing the inviting atmosphere.
Apartment in Shadyside
4.95 out of 5 average rating, 139 reviews

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

Modern and family oriented 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.

Guest favorite
A modern living area features a kitchenette with a small refrigerator and microwave, alongside a comfortable white chair and a sleek gray sofa. A wall-mounted TV displays a city skyline, while exposed brick adds a touch of character. Natural light filters in through a window.
Home in Friendship
4.88 out of 5 average rating, 541 reviews

PRIVATE MINI STUDIO (D2)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd 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
Apartment in Shadyside
4.88 out of 5 average rating, 49 reviews

Cozy Apt+Gym+EV+Free Onsite Parking+Near UPMC

Welcome to our stunning luxury 1-bed studio unit. Perfect for both business and leisure travellers, 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*

Top guest favorite
A cozy bedroom features a spacious bed dressed in an orange quilt. Two windows allow natural light to fill the room, and a colorful chair sits beside a small nightstand. A decorative fireplace adds character, complemented by framed artwork hanging above.
Guest suite in Bloomfield
4.98 out of 5 average rating, 215 reviews

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Guest favorite
An open-concept living area features a modern kitchen with white cabinetry and granite countertops. A comfortable sofa sits in front of a coffee table, while a mounted flat-screen television displays various streaming options. Soft lighting is provided by a ceiling fan and recessed lighting.
Apartment in Shadyside
4.92 out of 5 average rating, 118 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, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

Popular amenities for Shadyside vacation rentals

When is the best time to visit Shadyside?

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Avg. priceﺩ.ﺇ294ﺩ.ﺇ297ﺩ.ﺇ323ﺩ.ﺇ360ﺩ.ﺇ415ﺩ.ﺇ426ﺩ.ﺇ386ﺩ.ﺇ415ﺩ.ﺇ389ﺩ.ﺇ382ﺩ.ﺇ364ﺩ.ﺇ331
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Quick stats about vacation rentals in Shadyside

  • Total vacation rentals

    Explore 320 vacation rentals in Shadyside

  • Nightly prices starting at

    Shadyside vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 27,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    320 of Shadyside vacation rentals include wi-fi 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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