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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.

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Guest suite in Pittsburgh

4.65 out of 5 average rating, 158 reviews

Lovely Wightman entire 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 entire basement suite has been renovated and is fully furnished. It features a spacious living room, a full kitchen and a private entrance. There are one full bed and one twin bed in the bedroom and one sofa in the living room. The guests can also use laundry facilities. It is only minutes from nearby restaurants and beautiful Schenley Park. Very close to Pitt and CMU.

Rental unit in Pittsburgh

4.86 out of 5 average rating, 690 reviews

South Side Flats - Central to everything!

Artfully decorated, large, and open concept 1 bedroom apartment in the center of the South Side Flats entertainment district. Everything you need is within steps of your front door - restaurants, grocery, and entertainment. 5 min from downtown & within 15 min to anywhere in the city. IMPORTANT: This listing is exclusively for people visiting Pittsburgh. DO NOT book with us if you live in Allegheny County without 1st receiving permission from the host, or your reservation will be cancelled.

Guest favourite

Home in Pittsburgh

4.93 out of 5 average rating, 295 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.

Guest favourite

Rental unit in Pittsburgh

4.95 out of 5 average rating, 262 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

*PLENTY OF FREE STREET PARKING* 1 BDRM apt in the up and coming town of Bellevue, just a 10 min drive to downtown and the stadiums. This is a 2nd floor unit in my 100+ year old four-square home. It has a private entrance with a keypad for Airbnb guests, there are 2 other units in the building. Its in walking distance to public transit, shops, restaurants, places of worship, banks, and a grocery store. Pet friendly ($50 fee) just add your pet under pets in the guest section when booking.

Guest favourite

Rental unit in Pittsburgh

4.96 out of 5 average rating, 456 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Guest favourite

Rental unit in Pittsburgh

4.97 out of 5 average rating, 324 reviews

Apartment: Home Sweet Home

Enjoy yourself in a bright, one floor living space, with a separate bedroom, (Queen Size bed), bathroom (shower) and living room. Sleeps 4 comfortably. Queen size sofa bed in living room sleeps 2. Private entrance with lock box and private off street parking. 6 miles from Downtown Pittsburgh sports and activities. Close to shopping, pizza and restaurants. Uber available. Enjoy sweet bread or muffins with coffee or tea to begin your stay! We are happy to meet your needs!

Guest favourite

Guest suite in Pittsburgh

4.85 out of 5 average rating, 215 reviews

Entire private floor (giant Jacuzzi with shower!)

Welcome! In addition to having numerous "sparkling clean" reviews, I am committed to helping Airbnb guests stay safe by cleaning and disinfecting frequently touched surfaces. This is a finished basement in my house with its own entry way. Being below ground helps keep things cool in the summer. Off-street parking pad available in back of house (look for small Amish shed). Safe, quiet, and family-oriented neighborhood minutes from the Zoo, Highland Park, and downtown!

Guest favourite

Cabin in Pittsburgh

4.93 out of 5 average rating, 140 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost/night is $135.00 for 2 adults. Extra adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day.

Guest favourite

Rental unit in Pittsburgh

4.97 out of 5 average rating, 397 reviews

Modern Love Apartment - Heart of Lawrenceville!

This private apartment (with it's own entrance) is on the lowest level of our house. It is walking distance to the best of lively Lawrenceville. It is centrally located in Pittsburgh and close to downtown, the universities and the stadiums. We are right off of Butler Street which is where the shops and restaurants are located. There is free street parking directly in front of the house. Dozens of restaurants and shops are just a short walk away.

Guest suite in Pittsburgh

4.89 out of 5 average rating, 360 reviews

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).

Guest favourite

Guest suite in Pittsburgh

4.98 out of 5 average rating, 246 reviews

Large victorian 3rd flr apt in walkable eastend

An entire third floor apartment of a historic Colonial Revival house in the Friendship neighborhood. Two bedrooms, each with a firm queen memory foam bed, one bathroom with claw foot tub/shower, huge living room with seating area and desk, and a fully equipped kitchen with washer and dryer. Walk up to third floor. A queen air mattress bed or pack n' play can be added to any one of the bedrooms or the living room, just let us know.

Home in Pittsburgh

4.8 out of 5 average rating, 225 reviews

Sq. Hill 🏡 Frick Park 🚵‍♀️ Parking 👑 King Bed

Newly remodeled house in the Squirrel Hill neighborhood of Pittsburgh! Includes everything you need for a comfortable stay with friends & family. 🔑 4 BR/2.5 BA - Comfortably Sleeps 8 🔑 Self Check-in 🔑 Private Parking for 2 + Free Street Parking 🔑 Fully Equipped Kitchen w Brand New Appliances 🔑 Quiet Residential Street in the Quaint Neighborhood of Squirrel Hill 🍁 FRICK Park within Steps of your front door

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Popular amenities for Squirrel Hill family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Pittsburgh

4.89 out of 5 average rating, 90 reviews

Sunny Bunny Eco Luxe Art & Wellness House ()

Guest favourite

Home in Pittsburgh

5 out of 5 average rating, 17 reviews

Luxe Shadyside Spa + Parking + 5 Beds + Zen Garden

Guest favourite

Home in Pittsburgh

5 out of 5 average rating, 22 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

Guest favourite

Bungalow in Oakmont

4.96 out of 5 average rating, 57 reviews

Oakmont home with private hot tub

Guest favourite

Bungalow in Oakmont

4.99 out of 5 average rating, 71 reviews

Oakmont Home with Hot Tub

Family- and pet-friendly home rentals

Rental unit in Pittsburgh

4.71 out of 5 average rating, 66 reviews

Gorgeous and large 2 bedroom apt./home near city

Guest favourite

Home in Pittsburgh

4.9 out of 5 average rating, 29 reviews

House 3bed Free Parking Walk to Bars & Shops

Rental unit in Pittsburgh

4.88 out of 5 average rating, 291 reviews

Cozy + Modern apartment near the city!

Home in Pittsburgh

4.74 out of 5 average rating, 43 reviews

Squirrel Hill Elegant Bright House

Guest favourite

Home in Pittsburgh

4.97 out of 5 average rating, 325 reviews

Spacious Modern Home • Rooftop Deck

Guest favourite

Home in PITTSBURGH

4.93 out of 5 average rating, 43 reviews

Large Home Close to Everything in Pittsburgh

Rental unit in Pittsburgh

4.77 out of 5 average rating, 133 reviews

Beechwood BNB

Guest favourite

Home in Pittsburgh

5 out of 5 average rating, 216 reviews

High-End South Side 4 Bedroom House, sleeps 15!

Family-friendly home rentals with Wi-Fi

Rental unit in Pittsburgh

4.88 out of 5 average rating, 24 reviews

Large Studio Apt - Perfect if you're on a budget!

Guest favourite

Condo in Pittsburgh

4.97 out of 5 average rating, 38 reviews

Bright & sunny apt in Shadyside with free parking

Guest favourite

Loft in Pittsburgh

4.81 out of 5 average rating, 155 reviews

Artsy Loft Studio 1.1Mi To Downtown

Guest favourite

Guesthouse in Pittsburgh

4.99 out of 5 average rating, 94 reviews

Urban Eclectic II, Private Room/Entrance/Bath

Guest favourite

Home in Bellevue

4.99 out of 5 average rating, 68 reviews

Grand on Grant

Guest favourite

Home in Pittsburgh

5 out of 5 average rating, 18 reviews

High-End Modern w/ Roof Deck @ Awesome Location

Dome in Pittsburgh

4.58 out of 5 average rating, 40 reviews

*Dome Sweet Dome!* Up to 4 guests

Rental unit in Pittsburgh

4.79 out of 5 average rating, 24 reviews

Sunny, Elegant Modern - easy walk to stage AE

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