Holiday rentals in Shadyside, Pittsburgh

4.89 out of 5 average rating, 47 reviews

GYM+HULU+Parking+ Near UPMC|Universities|Shopping

Discover comfort and convenience in our charming city haven. Perfect for professionals and travelers, our apartment is your gateway to nearby dining, boutique stores, shopping outlets, & attractions. Building amenities include: 🏋🏻‍♂️State-Of-The-Art (24/7)Fitness Center 🚗FREE Street Parking for 1 Car(Based on Availability) 💼Private & Co-Working Spaces 🔌Level 2 EV Charging Station Available 🍵Complimentary Tea/Coffee Station 🏓Ping Pong Table, Comfy Seating Area 🍖Outdoor BBQ 🐾Pet Friendly

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.

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.

Top guest favourite

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.

4.99 out of 5 average rating, 83 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.

4.9 out of 5 average rating, 10 reviews

Lux King Bed | Free Parking + Gym | UPMC+CMU+Pitt

✨ Welcome to our large, stylish studio in the heart of Shadyside! This modern, fully furnished suite features sleek décor, a fully equipped kitchen, a cozy living space, and a luxurious king bed. Enjoy top-tier amenities, including: 🔹 Fitness Center & Yoga Studio 🔹 Free Street Parking 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Retail 🔹 Bike Storage Room

4.94 out of 5 average rating, 107 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.

5 out of 5 average rating, 16 reviews

Cozy Studio in Shadyside - Walk to CMU

Stay in your own little oasis in this cozy little studio located in the heart of Shadyside. Just walk five short blocks to grab your morning coffee or shop at Lululemon, Patagonia or Apple store on Walnut st. It's also in close proximity to CMU, PITT, and UPMC Shadyside making it an ideal place for students, professors and traveling nurses. CMU free shuttle stop is right in front of the building or you can walk to CMU and PITT campus. Come check us out at "Shadyside STAY".

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!

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!🔥

4.88 out of 5 average rating, 503 reviews

Home in Friendship

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).

4.88 out of 5 average rating, 16 reviews

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

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*

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Popular amenities for Shadyside, Pittsburgh holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Shadyside, Pittsburgh's top sights

Carnegie Mellon University10 locals recommend

Phipps Conservatory and Botanical Gardens97 locals recommend

Carnegie Museum of Art57 locals recommend

Other great holiday rentals in Shadyside, Pittsburgh

Top guest favourite

4.98 out of 5 average rating, 93 reviews

Cozy King Suite Just off Walnut

TayyabRating, 5 stars1 week ago

well established place in the heart of pittsburgh cozy place as described. Paul was helpful check in few time if I needed anything. highly recommended.

4.91 out of 5 average rating, 110 reviews

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

StevenRating, 5 stars1 week ago

This was a perfectly pleasant space in a charming neighborhood with lots of restaurants and stores in easy walking distance. Visitors should be aware that this is a basement apartment in a large house. (In retrospect, this should have been obvious from the photographs.)

4.88 out of 5 average rating, 256 reviews

Cozy & Central 2BR ~ Steps from Walnut St!

DavidRating, 5 stars3 days ago

Great place in a friendly neighborhood, perfect for walking or running. A hospital within walking distance. A bus line is within a few blocks of the house. A ton of restaurants are nearby. The unit is well-kept and clean.

4.88 out of 5 average rating, 169 reviews

Cozy 2BR steps from Walnut St!

ScottRating, 5 stars4 days ago

Jake was a responsive host. We had a few questions and needs during our stay. Jake responded with minutes and was respectful and helpful. The apartment was clean and had all we needed. The neighborhood is quiet, always found parking, and conveniently located near shops and restaurants. Quick trip downtown and to the pro sports venues. Highly recommend.

4.82 out of 5 average rating, 197 reviews

Flat in Friendship

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (B2)

NicholasRating, 5 stars4 days ago

really simple but clean and homey vibe. the place was very easy to find, very clean and close to grocery and places to eat.

4.85 out of 5 average rating, 494 reviews

Flat in Friendship

PRIVATE MINI STUDIO (C1)

JennieRating, 5 stars1 month ago

Pur stay was great! The place was super clean and very calm and peaceful. We were able to do laundry and there was complimentary tea snd soaps. Natallia was very accommodating with our request for a late check out. She reslonded right away to all of our questions.

Top guest favourite

Flat in East Liberty

4.97 out of 5 average rating, 111 reviews

Upscale King Bed Suite ~ Free parking & ADA!

AmberRating, 5 stars1 week ago

Another fantastic stay at Jake's place! I decided to go to the Phoneboy concert at the last minute, and Jake approved my request almost instantly, sending all the info I needed right away. I really appreciate how responsive he is! And the accessible parking spot was a great bonus! As always, thank you very much, and I highly recommend Jake as a host!