
Family-friendly holiday rentals in Squirrel Hill
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Squirrel Hill
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

Industrial Loft 5 min to UPMC Shadyside CMU Pitt,
Come and relax in our new location! This historic warehouse was converted into apartments but still holds its original architectural features! Enjoy the industrial modern aesthetic with 15-foot-high ceilings, brick walls, original concrete floors, and atrium skylights with natural light. These units come fully furnished and most have full kitchens and all your required accessories for you to just drop your suitcase and start relaxing. **NOW PET FRIENDLY-$50.00 PET FEE PER STAY**

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.

Cozy and Spacious Guest Suite in Greenfield
This newly renovated suite is the downstairs unit of a three story house (the upper two floors are a completely separate living area). This space has plenty of free street parking located just outside of its own entrance. Carnegie Mellon University and the University of Pittsburgh are both about a 5-7 minute drive away, and to get downtown it is typically a 10 minute drive. There is a bus stop at the end of the street that can take you just about anywhere in Pittsburgh.

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.

PRIVATE MINI STUDIO (D1)
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).

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.

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.
Popular amenities for Squirrel Hill family-friendly rentals
Family-friendly home rentals with a hot tub

"The Spa Room" Renovated Flashlight Factory

420 friendly Luxury loft apt w jet tub & balcony

Secluded Hilltop Hideaway~Hot Tub~Two Living Rooms

NEW! Luxurious 5bdr w/ a hot tub. Walk to stadiums

Mountain Retreat in the Heart of the City

HotTub/Firepit/Parking! Less than 1mi PNC Park

hot tub fire pit Art & Wellness Retreat

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!
Family- and pet-friendly home rentals

Entire home near Kennywood without extra fees.

Large house to relax with friends and family

Seneca Place: A historic home in Mount Lebanon.

Cozy + Modern apartment near the city!

504 Bascom Ave Serene Luxury

Hilltop Suite, Quiet Street

1 Bed, idyllic, stadiums, free parking, & Pets OK

Cozy 2 bedrooms unit - 10 minutes to Downtown
Family-friendly home rentals with a pool

1st Fl. Huge Flat on 2 Acres - Pets/Garage Parking

Convenient townhome

Renovated Cozy Duplex w/pool, Close to downtown

Monroeville Bella

PIT Staycation Retreat with Pool House!

20 mins to Downtown- pool table & fenced yard

3BR, 2 Bath Home -Pool, Scenary, 20 mins to Pgh

Luxury 1BDWith Balcony+StunningWaterfrontViews
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Rappahannock River Holiday rentals
- Niagara Falls Holiday rentals
- Rentals with a patio Squirrel Hill
- Rentals with outdoor seating Squirrel Hill
- Rentals with a fireplace Squirrel Hill
- Rentals with breakfast Squirrel Hill
- Rentals with a washing machine and dryer Squirrel Hill
- Pet-friendly rentals Squirrel Hill
- House rentals Squirrel Hill
- Townhouse rentals Squirrel Hill
- Apartment rentals Squirrel Hill
- Fitness-friendly rentals Squirrel Hill
- Rentals with a fire pit Squirrel Hill
- Family-friendly rentals Pittsburgh
- Family-friendly rentals Allegheny County
- Family-friendly rentals Pennsylvania
- Family-friendly rentals United States
- PNC Park
- Carnegie Mellon University
- Seven Springs Mountain Resort
- Strip District
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Acrisure Stadium
- Idlewild & SoakZone
- Point State Park
- Kennywood
- National Aviary
- Raccoon Creek State Park
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- University Of Pittsburgh
- Schenley Park
- David Lawrence Convention Center
- Carnegie Museum of Art
- Children's Museum of Pittsburgh
- Randyland
- Senator John Heinz History Center
- Cathedral of Learning
- Stage AE
- Carnegie Science Center




