Family-friendly holiday rentals in Penn Hills

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Penn Hills

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Superhost

Home in Monroeville

4.85 out of 5 average rating, 167 reviews

Mayberry Escape

Discover the charm of this inviting 3-bed, 3.5-bath Monroeville home! Immerse yourself in luxury with a heated pool (seasonal), rejuvenating infrared sauna, expansive decks, a private backyard, a fully equipped kitchen, a finished basement, and a delightful fire pit overlooking the pool. Experience comfort and style with off-street parking included. Enquire now to make this your own sanctuary! ***If you enjoy this space, the owners are amenable to selling. Please contact for more information***

Top guest favourite

Flat in Coraopolis

4.97 out of 5 average rating, 197 reviews

Moon Professional Living Suite B

Recently updated 1 bedroom 2nd floor efficiency apt. w/ everything you will need for a comfortable stay. We do have 2 Airbnb Apartments available. We follow all Airbnb standards to provide a safe, quiet, sparkling clean, comfortable experience for all & ask you do the same. Minutes from the airport & short drive to downtown Pittsburgh. Shopping & dining nearby. Perfect for out of town guests & business travelers. Live far from the airport & have an early flight? Come stay at Cozy in Coraopolis.

Top guest favourite

Cabin in Pittsburgh

4.93 out of 5 average rating, 153 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 you see per night is for 2 guests. Added 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. I will collect that later.

Top guest favourite

Home in Bloomfield

4.98 out of 5 average rating, 196 reviews

PBR - Pittsburgh Bloomfield Rowhouse

A fully renovated, charming, and comfortable home in the heart of Pittsburgh's Little Italy. Location is just steps away from great dining, shopping, and entertainment. Historic Bloomfield is centrally located in the city and only minutes from local universities, hospitals, and stadiums. This pet friendly 3 bedroom house is perfect for families, friends, and business travelers. Whether you are visiting for work or leisure, this house will make your stay even more delightful. We welcome all!

Guest favourite

Home in Mexican War Streets

4.85 out of 5 average rating, 168 reviews

Walk to downtown, stadiums

Cozy and comfortable row house in the beautiful, historic Mexican War Streets. All the amenities of home—including linens, toiletries, kitchen supplies, tankless hot water heater (unlimited hot water)—and within walking distance to downtown, both stadiums, the Riverwalk, Children's museum, National Aviary, Mattress Factory museum, Andy Warhol Museum, and Rivers Casino. Backyard perfect for entertaining with grill and fire pit. Across the street from Randyland Pittsburgh, a must see for all!

Guest favourite

Home in Squirrel Hill South

4.93 out of 5 average rating, 314 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.

Top guest favourite

Home in South Side Flats

5 out of 5 average rating, 222 reviews

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

Newly Remodeled, Gorgeous High-End 4 Bedroom, 3 Full Bathroom entire house in the heart of Pittsburgh's historic South Side neighborhood; SLEEPS UP TO 15 PEOPLE; Pets welcome; Private/Enclosed Patio Hardwood floors, raised tin ceilings on first floor; open floor plan living room/kitchen with stainless-steel appliances, marble-counter-tops, Keurig, 70 inch TV, WiFi, Convenient 2nd floor laundry facilities,HD Televisions in every bedroom w/ Cable, Luxurious Memory Foam Beds

Guest favourite

Home in Bloomfield

4.9 out of 5 average rating, 249 reviews

Cozy home in "Little Italy"

Weekly 20% disc $924- 7 days Monthly 35% disc $3260 Nice spacious home on quiet street in Pittsburgh's "little Italy".(Bloomfield) Two blocks from Children's Hospital. One two and five minutes from three bus lines to downtown Pittsburgh. 8 minutes to 31st Street Studios. (Same bus lines) Walk to many fine restaurants on Liberty Ave. Off street parking.( 2 vehicles) One block from historic Allegheny cemetery. (2nd biggest cemetery in US)

Top guest favourite

Guest suite in Bloomfield

4.98 out of 5 average rating, 251 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.

Superhost

Home in Squirrel Hill South

4.81 out of 5 average rating, 239 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

Superhost

Flat in Bloomfield

4.78 out of 5 average rating, 583 reviews

Apt 1 Lawrenceville private 1br

Our place is close to nightlife, public transport, the city center, and parks. Kick back and relax in this fully furnished apartment, smart HDTV, fully-equipped kitchent, free wifi, cable, bike rental right across the street. You would love the location, the coziness. place is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favourite

Home in Leechburg

4.9 out of 5 average rating, 157 reviews

Getaway On the River and Bike Adventure

Clean and comfortable home on the Kiskiminetas River. Walk, bike or drive to restaurants and shops in Leechburg. Bike on the Leechburg Tow Path Trail which connects to downtown Leechburg and hundreds of miles of rails to trails in Armstrong County. Float, kayak and fish on the river all within a 40 minute drive to downtown Pittsburgh.