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Family-friendly vacation 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

4.64 out of 5 average rating, 155 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.

Feb 11 – 18

R2,474 ZAR per night

Apartment in Pittsburgh

4.86 out of 5 average rating, 646 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.

Jan 31 – Feb 7

R1,678 ZAR per night

Home in Pittsburgh

4.92 out of 5 average rating, 264 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.

Oct 1 – 8

R2,434 ZAR per night

Apartment in Point Breeze

4.95 out of 5 average rating, 388 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!

Jul 24 – 31

R1,760 ZAR per night

Home in Pittsburgh

4.82 out of 5 average rating, 129 reviews

New remodeled Modern 2BR suite for 4

This newly renovated, state of the art, private apartment is sure to make your stay in Pittsburgh enjoyable. Modern yet comfortable this apartment boasts granite countertops and a luxuriously tiled bathroom with a washer and dryer for your every day needs. Located in the heart of Squirrel Hill, right near Schenley park, PITT, CMU, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Downtown, Museums & Galleries, and all Sports venues.

May 18 – 25

R2,421 ZAR per night

Apartment in Pittsburgh

4.97 out of 5 average rating, 309 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!

Oct 21 – 28

R2,568 ZAR per night

Apartment in Pittsburgh

4.97 out of 5 average rating, 377 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.

Sep 1 – 8

R2,439 ZAR per night

Home in Pittsburgh

4.88 out of 5 average rating, 421 reviews

PRIVATE MINI STUDIO (D2)

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).

Nov 27 – Dec 4

R1,733 ZAR per night

Home in Squirrel Hill South

4.81 out of 5 average rating, 206 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

Sep 23 – 30

R6,988 ZAR per night

Guest suite in Pittsburgh

4.98 out of 5 average rating, 232 reviews

Large victorian 3rd flr apt in walkable eastend

An entire third floor apartment of a historic Colonial Revival house. 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.

Jul 29 – Aug 5

R2,810 ZAR per night

Cottage in Glenshaw

4.93 out of 5 average rating, 387 reviews

Glenshaw Guesthouse

A one bedroom cottage, on the historic grounds of Glenshaw's "Shaw House". The guesthouse was built on the foundation of a 200-year-old farm shed, nestled against a wooded hillside. Convenient free parking with lots of foliage and privacy. The space feels like it is in the country, but is a short 8 miles from downtown Pittsburgh.

Aug 22 – 29

R2,685 ZAR per night

Home in Pittsburgh

4.98 out of 5 average rating, 155 reviews

Spacious, attractive apartment in residential home

This cozy, sunny third-floor apartment is in a quiet neighborhood near Frick Park and easy walking to restaurants, bars, and coffee shops. The apartment is excellent for couples, solo adventurers, and business travelers, and it's located a short block from the busway to downtown and Oakland.

Oct 17 – 24

R1,962 ZAR per night

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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 suite in Pittsburgh

4.84 out of 5 average rating, 206 reviews

Entire private floor (giant Jacuzzi with shower!)

Jun 17 – 24

R2,253 ZAR per night

Bungalow in Oakmont

4.98 out of 5 average rating, 64 reviews

Oakmont Home with Hot Tub

R3,292 ZAR per night

Home in Shadyside

5.0 out of 5 average rating, 10 reviews

Luxe Shadyside Spa + Parking + 5 Beds + Zen Garden

Jun 22 – 29

R6,820 ZAR per night

Home in Pittsburgh

5.0 out of 5 average rating, 17 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

Dec 21 – 28

R13,512 ZAR per night

Home in Pittsburgh

4.88 out of 5 average rating, 73 reviews

Sunny Bunny Eco Luxe Art & Wellness House (Green)

Mar 9 – 16

R11,293 ZAR per night

Family- and pet-friendly home rentals

Apartment in Pittsburgh

4.87 out of 5 average rating, 280 reviews

Cozy + Modern apartment near the city!

Jun 7 – 14

R1,660 ZAR per night

Apartment in Pittsburgh

4.95 out of 5 average rating, 241 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

Apr 3 – 10

R2,095 ZAR per night

Cabin in Pittsburgh

4.92 out of 5 average rating, 127 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Jan 31 – Feb 7

R2,906 ZAR per night

Townhouse in Pittsburgh

4.93 out of 5 average rating, 320 reviews

Charming Home • Vibrant Neighborhood

Mar 6 – 13

R4,457 ZAR per night

Home in Monroeville

4.84 out of 5 average rating, 140 reviews

Mayberry Escape

Aug 16 – 23

R9,981 ZAR per night

Home in Pittsburgh

5.0 out of 5 average rating, 208 reviews

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

Jul 14 – 21

R11,295 ZAR per night

Townhouse in Pittsburgh

4.88 out of 5 average rating, 99 reviews

Modern/Industrial Townhouse in Lawrenceville

Aug 21 – 28

R1,655 ZAR per night

Home in Pittsburgh

4.91 out of 5 average rating, 11 reviews

House 3bed Free Parking Walk to Bars & Shops

Sep 10 – 17

R4,071 ZAR per night

Family-friendly home rentals with Wifi

Home in Pittsburgh

4.98 out of 5 average rating, 179 reviews

PBR - Pittsburgh Bloomfield Rowhouse

Feb 12 – 19

R3,208 ZAR per night

Home in Pittsburgh

4.92 out of 5 average rating, 228 reviews

Cozy home in "Little Italy"

Jun 10 – 17

R2,992 ZAR per night

Home in Munhall

4.8 out of 5 average rating, 218 reviews

Beautiful 3 Bedroom Home Cozy Front and Back Porch

Dec 7 – 14

R1,913 ZAR per night

Apartment in Bloomfield

4.81 out of 5 average rating, 270 reviews

Apt 7 Bloomfield/Lawrenceville private mini studio

Jun 7 – 14

R2,024 ZAR per night

Apartment in Pittsburgh

4.92 out of 5 average rating, 410 reviews

Historic Charmer | Spacious | Off Street Parking

Aug 21 – 28

R2,164 ZAR per night

Townhouse in Pittsburgh

4.81 out of 5 average rating, 179 reviews

2BR home in very hip neighborhood

Feb 18 – 25

R2,337 ZAR per night

Home in Pittsburgh

4.97 out of 5 average rating, 154 reviews

Luxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks

Aug 24 – 31

R12,847 ZAR per night

Apartment in Pittsburgh

4.83 out of 5 average rating, 485 reviews

Renovated top floor unit! Close to downtown!

Oct 20 – 27

R1,547 ZAR per night

Destinations to explore