Vacation rentals with outdoor seating in Squirrel Hill

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.

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet

Stylish and freshly renovated 1 BR/ 1 bath apartment perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! Fully equipped for an extended stay, weekend getaway, or just a place to crash for the night. ⭐️Super comfy queen memory foam mattress 🌟24/7 Guest support ⭐️Free off-street parking! 🌟Fully stocked & equipped kitchen ⭐️Queen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ⭐️Laundry (Free and in-unit)

East End Gem | Your Home Away from Home

This bright, stylish, and comfortable space, designed by an HGTV producer! With a fully remodeled kitchen and bathroom, cozy beds, and inviting rooms, this home offers the perfect home away from home. Conveniently located within 20 minutes of everything Pittsburgh has to offer, including sports fields, rivers, bridges, shopping, museums, historical sites, music venues, universities, and more! Whether you're here for business or pleasure, you'll find everything you need for a relaxing stay.

"The Cottage on Summit"

The "Cottage on Summit" is FIVE STAR, charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . SPECIAL NOTE: AIRBNB "now includes" rates and fees as the TOTAL STAY cost for transparency. NIGHT RATE AIRBNB SERVICE FEE CLEANING NOT INCLUDED LOCAL TAXES (14%) YOU MUST BE 25 OR OLDER ID's May Be Checked

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.

Shadyside/Central @4 Stylish&Central Studio w/Prkg

Stylish and Central family oriented modern 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).

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely 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 CMU/Pitt 2025-3rd 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.