Family-friendly vacation rentals in Squirrel Hill

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

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.

Darling basement one-bedroom

This simple basement suite is safe and convenient. Located on a quiet street with walking to restaurants, library, and movie theater with easy bus access to Pitt, CMU. Equidistant to Frick and Schenley Parks with hiking and biking trails, tennis, soccer, playground. Private entrance, off steep-ish driveway . Free street parking. Lower ceiling. No pets, smoking outside only. I have my children every other weekend; they have quiet hours 9pm-8am. Please inquire for dates if that might annoy.

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!

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/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 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.

Cheerful 3-bedroom home with on-street parking

Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

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.

Spacious, warm, private apartment near CMU /Pitt

Spacious, warm, private apartment with parking set in a beautiful, quiet, family neighborhood. Just minutes away walking from CMU (10 Min) and Pitt 20 Min). And a 4 minute walk Bus stop (61xx) to all of Pittsburgh. Shadyside, Squirrel Hill and the Carnegie museums are in the immediate neighborhood with great options for dining and entertainment. Also the Phipps Conservatory and Botanical Gardens are only 1.3 Miles from the house.

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

Lovely, cozy Murray guest suite in Squirrel Hill

This lovely and cozy one-bedroom guest suite is located in a safe and convenient neighborhood in the heart of squirrel hill. The suite is fully renovated with welcome color and modern furniture. The suite has a private entrance. There are shared laundry facilities for our guests. Our high quality bedding ensures you have a nice rest after a busy day. It is only minutes from nearby restaurants. Very close to Pitt and CMU.