Holiday rentals with outdoor seating in Shadyside

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Newly renovated 1brm studio. Close to everything!

Welcome to Casa Gringa! We are a stone's throw away from everything exciting Pittsburgh has to offer. We are literally a 10 minute walk to the zoo! Newly remodeled 1 bedroom basement studio. Guests will have their own private entrance with a smart lock, access to the yard, and on-site parking. The neighborhood is very safe, quiet, and family oriented Upon booking, we will send you a welcome message with a link to our digital Casa Gringa Guide. PLEASE READ THE HOUSE RULES IN THE APP B4 BOOKING

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.

Off-Street Parking, Steps to Butler St., Patio!

In the heart of lower Lawrenceville, our place exudes historic Pittsburgh charm while providing an incredibly cozy experience. Our spacious kitchen invites you to cook a great dinner. Our comfortable living room surrounded by historic brickwork + open staircase encourages you to relax and watch Netflix. The patio welcomes you with fresh air. With two full bathrooms, two couples or a family can get ready for the day (or night!) Within walking distance, bars, breweries, and restaurants abound!

Luxury King Suite Near Shadyside Hospital

The Pitt Shuttle is just a block away, and the apartment is 0.8 miles from Pitt and CMU campuses. This newly remodeled 2BR/1BA first-floor apartment is fully stocked and pristine, perfect for a Steeler game, family getaway, or hospital visit. Close to UPMC Shadyside, UPMC Presby, West Penn, and the VA, with restaurants, bars, and shops within walking distance. Whether you're visiting for work or play, this stylish apartment offers the comfort and convenience you need to feel at home.

Stunning 2 BR King Bed Suite ~ Steps from Walnut

Stunning & upscale 2 BR/ 1 bathroom perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! ⭐️2 beds (1 King/ 1 Queen; High end memory foam mattresses) ⭐️Sleeper sofa (Queen) ⭐️Pet Friendly ⭐️Free washer/ dryer (Basement) ⭐️Fully stocked & equipped kitchen ⭐️Private back porch My team & I are here for you 24/7 before, during and after your stay with us! Message us if you have any questions or feel free to instant book!

Cute Apt Minutes from Downtown and Stadiums!

🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

Urban serenity, privacy in charming carriage house

Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

Shadyside 2Bed 2Bath w/ Parking!

2 OFF STREET PARKING SPACES INCLUDED FOR FREE! In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 2BR/2 bath apartment in a prime location, restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

W. Shadyside NFL draft 2026 -3rd floor apt

“A hidden gem. Lovely apartment in a beautiful house on a fantastic street in Pittsburgh with access to many other parts of the city " Two blocks from 5th Ave and Walnut Street. Ten minutes from CMU, (via Devon Road) and their world class computer AI, GS, and INI departments. A perfect location for your Shadyside activities. Safe and secure with off street parking, if necessary. Plus just around the corner from McCookMansion on 5th and their beautiful bar/restaurant.

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.

Private East Liberty Flat

Private one-bedroom flat in renovated East Liberty row house. Great central location. Walking distance to parks, shops, restaurants. Easy access to public transportation. Queen bed. Dining/desk area. Full kitchen with electric range, dishwasher, refrigerator, coffee maker, kettle, toaster and a microwave. Filtered cold water in fridge. Wireless internet. Radiant floor heating. Window air conditioning. Private entrance with keypad lock. Hosts live n