Family-friendly holiday rentals in Squirrel Hill

4.96 out of 5 average rating, 100 reviews

Townhouse in Pittsburgh

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.

Guest suite in Pittsburgh

4.98 out of 5 average rating, 265 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.

4.91 out of 5 average rating, 161 reviews

Cozy King Suite with Parking!

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!

4.91 out of 5 average rating, 267 reviews

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)

4.92 out of 5 average rating, 329 reviews

Home in Pittsburgh

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.

4.76 out of 5 average rating, 567 reviews

Quaint cozy Shadyside One Bedroom

Cozy apartment located in Shadyside.Just steps away from Shadyside Hospital, this apartment is great for long or short term visitors.Grocery stores, restaurants, bars, and shops are all just a few minute walk from this apartment as well. The apartment is a short drive to Heinz Field, PPG Paints Arena, PNC Park, and all the amazing museums Pittsburgh has to offer! Also near by is CMU, PITT, Chatham Univeristy, and Carlow College.Free parking & WiFi.Towels,bed linens,toilet paper provided.

4.96 out of 5 average rating, 111 reviews

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.

4.98 out of 5 average rating, 126 reviews

"April's Retreat" Regent Square King Bed Frick Prk

Take it easy at this tranquil getaway that is close to everything Pittsburgh. You'll enjoy the one bedroom apartment on the 2nd floor of this historic building in Regent Square. Walk to Frick Park, restaurants, coffee shops and bars on Braddock. Hike or mountain bike on the 22 miles of trails. Small and well-appointed kitchen if you like to prepare your own meals. Tons of natural light. Close to bus routes. Need more space? Traveling with others? Check out my other 2bd listing.

4.94 out of 5 average rating, 159 reviews

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

This 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 it is reserved in advance. The apartment sleeps 4 people. The bedroom has a king bed. The living room has a sofa that very conveniently folds down to transform into a queen-sized bed. There is a spacious deck.

4.84 out of 5 average rating, 233 reviews

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

This Bright basement studio is for anyone needing a stylish, clean place to stay while visiting Pittsburgh. It has a new queen bed, sleeper sofa, desk, bar and a very large bathroom. It has a private entrance at the back of a beautiful 1890s Pittsburgh mansion. It works very well for travelers 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).

Guest suite in Pittsburgh

4.91 out of 5 average rating, 230 reviews

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.