Family-friendly holiday rentals in Squirrel Hill

Huge Open Concept 2BR by Walnut

HUGE apartment In the heart of Shadyside w/ room for the whole family! 1 Block to Walnut St & FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 2 floor apt in a prime location, w/ all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, & fitness studios close by. The building was gutted & remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances is brand new!

Minimalist Townhouse with Stunning Skyline View

This townhouse is a gem in Pittsburgh! Located on a quiet street in Greenfield, it is central to everything the city has to offer. Situated on top of a hill, the skyline can be seen from the deck, and it’s breathtaking with a sunset! Walkable to Squirrel hill, less than 10 minutes driving from downtown, Shadyside, Oakland. The cohost has lived in Pittsburgh for 6 years and would be delighted to offer recommendations around the city. Meticulous cleaning standards are followed for your safety.

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.

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

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.

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 (Free & Shared) ⭐️Pull out bed (Full) 🔥Message today to secure your reservation!🔥

Cozy Entire APT B Friendship Park & Free Parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

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).

"April's Haven" Regent Square King Frick Park

Take a break and unwind at this peaceful retreat. Two bedroom third floor apartment walking distance to Frick Park, shops, restaurants, and bars on Braddock. Quiet historic neighborhood with brick streets. Hike or mountain bike on the 22 miles of trails in fabulous Frick Park. Short drive or easy bus ride to universities and UPMC facilities. Don't need 2 bedrooms? Traveling with others? Check out my other 1bd listing. https://air.tl/JAWjri9Y

Renovated large private studio in Squirrel Hill

Cozy and lovely large studio with garden, separate private entrance, kitchen, and full bathroom. Located in the central and convenient neighborhood of Squirrel Hill, close to CMU, University of Pittsburgh and Chatham University, right next to Schenley Park and walking distance (only 2 blocks) to all the cafes, restaurants, shops, movie theater and local amenities of our amazing neighborhood. Downtown Pittsburgh is only 10-12 minutes drive.

Newly remodeled 2 bedroom apartment

Newly remodeled 2 bedroom apartment on the first floor of a duplex located in a quiet neighborhood. Fully equipped kitchen. Roku Tv with cable and free wifi. Plenty of on street parking. Walking distance to Frick Park and great neighborhood bars/ restaurants. Under one mile to Regent Square bars and restaurants. Just a few minute car ride to the heart of Squirrel Hill. Under ten minute car ride to downtown Pittsburgh. Self check-in.

Sq. Hill 🏡 Frick Park 🚵‍♀️ Parking 👑 King Bed

Newly remodeled house in the Squirrel Hill neighborhood of Pittsburgh! Includes everything you need for a comfortable stay with friends & family. 🔑 4 BR/2.5 BA - Comfortably Sleeps 8 🔑 Self Check-in 🔑 Private Parking for 2 + Free Street Parking 🔑 Fully Equipped Kitchen w Brand New Appliances 🔑 Quiet Residential Street in the Quaint Neighborhood of Squirrel Hill 🍁 FRICK Park within Steps of your front door