Family-friendly vacation rentals in Squirrel Hill

A cozy living room area showcases a brown leather sofa adorned with decorative pillows. Two lamps illuminate the space, and a round coffee table is positioned in front of the sofa. Artwork is displayed on the walls, contributing to the classic decor.

4.99 out of 5 average rating, 125 reviews

2BR Apt. /Pittsburgh/East/Regent Square/Frick Park

First floor 2-bedroom apartment with classic decor. Modern bath/kitchen with complete utensils. Wi-Fi & wired gigabit network. Two TVs with service. Appropriate for business traveler, families with older children. Living and dining room accommodates 8-10 people. Convenient to downtown, Oakland/universities. Across street parking. Nearby restaurant/stores and park in walking distance. Open bar. No per-person or amenities charges. Virtual tour at https://my.matterport.com/show/?m=BFeAkSV4ekM

4.95 out of 5 average rating, 110 reviews

The exterior of the townhouse features warm-toned brick walls with traditional window accents. A welcoming front porch is highlighted by a red door and two chairs. Lush green grass and blooming yellow flowers provide a vibrant contrast against the brick facade.

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.

A mid-sized living room features a gray futon and several chairs arranged around a light-colored coffee table. An area rug with a floral pattern covers the floor, and a cozy ambiance is provided by overhead lights and lamps. Exposed wooden panels bring warmth to the space.

4.83 out of 5 average rating, 146 reviews

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.

An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.

4.94 out of 5 average rating, 180 reviews

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!

A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.

4.98 out of 5 average rating, 108 reviews

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

A modern living room features a comfortable sofa with decorative pillows, complemented by an armchair and a coffee table. The kitchen area showcases a marble countertop, with bar stools provided for dining. Bright wall art enhances the space, illuminated by natural light from the window.

4.92 out of 5 average rating, 338 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)

The kitchen area features dark wood cabinetry with a granite countertop. Stainless steel appliances, including a microwave and refrigerator, are neatly installed. A tiled backsplash in a soft grey hue complements the modern design. A small dining table with two chairs occupies the space.

4.93 out of 5 average rating, 368 reviews

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.

4.89 out of 5 average rating, 131 reviews

Victorian home 2 bedroom Shadyside

Bright, sunny, spacious 2 bedroom apartment with 1 parking space in the heart of Shadyside. This apartment is in a Victorian home on a quiet street. There is a train that runs below the street I feel it is part of the history and charm of city living. Shopping, restaurants, UPMC hospitals, Universities, museums and cultural activities, within walking distance or public transportation. The unit has been recently updated, beautiful new bathroom and hardwood flooring through out.

4.92 out of 5 average rating, 217 reviews

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.

A modern bedroom is characterized by sloped wooden ceilings and exposed beams. A spacious bed with a light gray coverlet is centered against the wall, flanked by two bedside tables with lamps. Natural light enters through a small window, illuminating the wooden floor.

4.87 out of 5 average rating, 275 reviews

Shadyside/Pittsburgh, Modern & Unique 1BD w/Prkng

Unique 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.

A wooden staircase leads to the upper level, framed by polished handrails and original woodwork. A woven runner rug adds texture to the hardwood floor. A small console table stands against the wall, paired with a green potted plant. Light filters in through a nearby doorway.

5 out of 5 average rating, 108 reviews

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.

A modern living area features a light grey sectional sofa draped with a vibrant orange throw. Colorful artwork adorns the wall above a sleek television, while a spiral staircase provides access to the upper levels. A dining area with pink chairs is visible in the background.