Family-friendly holiday rentals in Squirrel Hill

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

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.

Secret Garden by Frick Park with Garage Parking

Disappear into the secret garden of this unique centrally located apartment a few blocks from Frick Park. Steps from Regent Square, a short walk to Point Breeze, close to universities, hospitals, Oakland, Bakery Square, and Rockwell Park. Easy access to 376 Parkway, and 10 to 15 min to downtown. 15 min from Monroeville. This listing is great for anyone who wants some peace and quiet at the end of the day. Located on a dead end street there is little traffic noise to interrupt your relaxation.

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!

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!

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.

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.

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

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.

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

Modern and family oriented 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.

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.