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

Groovy Retro Get-Away

With a retro flare & a mid-century modern vibe, you'll enjoy this quaint bungalow in a quiet residential neighborhood conveniently located minutes from downtown Pittsburgh, the airport, many great sites, must-see attractions, universities & colleges. Whether you're in town for business, a sports event, bringing a student back to school or just want some time away, this cozy space is perfect! Everything in this bungalow is well appointed including keurig coffee, WiFi & a smart TV for streaming.

HOT TUB KING bed Luxurious 2 bed in PRIME location

Enjoy a stylish experience at this centrally-located getaway. I believe in maximum comfort. All the comforts and amenities of home and more; including memory foam beds, smart tv, nespresso machine, and more. *5 miles from Heinz Field *20 minute walk to Lawrenceville strip *10 minute walk to Children's Hospital *1 mile from Shadyside *5 minute walk to West Penn Hospital This is the ultimate spot for a couples retreat or extended stay... NO PARTIES ALLOWED:) Please note the open stair case!

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.

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!

Bright Garfield rowhome with fenced-in yard

Walk to anything you need from this cozy, bright rowhome in Pittsburgh's Garfield neighborhood! Best for couples or remote workers, but can accommodate up to four guests. The second bedroom doubles as a workspace. There is a fenced-in backyard for guest use. 5-minute walk to Penn Ave bars, shops, restaurants, grocery stores & more. Convenient access to bus lines & surrounding neighborhoods of East Liberty, Shadyside, Bloomfield, Oakland, Lawrenceville, Highland Park, & the Strip District.

Shadyside/Central @5 Stylish&Bright Studio w/Prkg

Modern and Stylish family oriented bright Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen 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.

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Walk to CMU, Pitt, Shadyside! King Suite! Parking!

This remodeled apartment is in an ideal location in Shadyside close 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 for free if you reserve it in advance. The apartment sleeps 4 people. The bedroom has a king bed. The living room has a sofa couch that very conveniently folds down to transform into a queen-sized bed.

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

Le Petit Riad: A Moroccan Oasis

Le Petit Riad, "The Little Courtyard" in French, is an immersive Moroccan experience. Inspired by Chefchaouen, the sapphire colored city, this is a tiny space with big IMPACT. Every meticulous detail will leave you wondering if somehow, magically, you ended up on a flight to the Mediterranean, instead of PIT. Nestled in a quiet alley literally steps from Butler Street and all Lawrenceville, the hottest hood in Pittsburgh, has to offer.