Family-friendly vacation rentals in Shadyside, Pittsburgh

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Top-rated family-friendly rentals in Shadyside, Pittsburgh

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

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Superhost

A living space is presented with a neutral color palette. A couch and chair are arranged around a small coffee table. A dining area with a table and four chairs is visible in the background. Natural light filters through vertical blinds on a nearby window, illuminating the space.

Apartment in Shadyside

4.78 out of 5 average rating, 652 reviews

Sunny Spacious Shadyside 1 bedroom

Bright one bedroom apartment can sleep up to three.Centrally located and just steps from Shadyside Hospital.The apartment offers guests easy access to numerous attractions, museums, stadiums, and concert venues.Just a few minutes walk to bars, restaurants, grocery stores, and shopping.This quaint apartment is perfect for a short or long term stay.Designated parking space makes it easy for you to come and go as you please.Fully equipped kitchen.Public transportation and rentable bikes close by.

Top guest favorite

A spacious living room features a stylish brick accent wall. Comfortable seating is arranged around a low coffee table, and a large flat-screen television is positioned on a media console. Natural light fills the area, highlighting a decorative wall piece and a small door leading to another room.

Home in Bloomfield

4.98 out of 5 average rating, 197 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 favorite

The kitchen area features dark wood cabinetry with a granite countertop. Stainless steel appliances, including a microwave and refrigerator, are neatly installed. A tiled backsplash in a soft grey hue complements the modern design. A small dining table with two chairs occupies the space.

Home in Squirrel Hill South

4.93 out of 5 average rating, 315 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 favorite

A cozy sleeping area features a wooden queen-sized bed with a textured white duvet and two bedside lamps. A comfortable chair is positioned in the corner, and natural light filters through a small window, creating a tranquil atmosphere.

Apartment in Point Breeze

4.96 out of 5 average rating, 493 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!

Top guest favorite

A modern, architect-designed house features a striking facade with large windows and a combination of grey and natural wood siding. A red front door and matching railing add a pop of color, while a landscaped yard is visible in the foreground.

Apartment in Pittsburgh

4.97 out of 5 average rating, 417 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.

Superhost

A spacious living area features a comfortable gray sofa set and a small coffee table. A mounted flat-screen TV is visible on one wall, while a kitchenette with modern appliances is positioned adjacent to it, highlighted by natural light from a nearby window.

Guest suite in Bloomfield

4.9 out of 5 average rating, 391 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).

Superhost

The front view of a spacious home is displayed, featuring a welcoming entrance and a large back porch. Outdoor lighting enhances the structure as a vehicle is parked in the driveway. The second-floor balcony offers a view of the surrounding area, visible in the evening light.

Home in Bloomfield

4.89 out of 5 average rating, 250 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)

Superhost

A living area features dark leather seating arrangements, including a spacious sofa and a matching loveseat. A coffee table with decorative flowers complements the furnishings. Natural light is available through an adjacent doorway, with a smart TV mounted on the wall, creating an inviting space.

Apartment in Bloomfield

4.9 out of 5 average rating, 246 reviews

5161 PENN AVE #1 Urban 1 Br Apartment with parking

You will love this beautiful, newly renovated apartment! Conveniently located on Penn ave. Aldi and Family Dollar stores directly across the street. On a bus line. Eat-in kitchen. 1 br with Queen size bed. Full size futon in Living room. Bathroom with walk-in shower. We try to provide all the necessities so you can live comfortably during your stay. If you find that we miss something - please let us know and we'll try to accommodate.

Top guest favorite

A spacious living room featuring a blend of modern and classic decor. Two comfortable sofas and a single armchair surround a coffee table, with a vibrant area rug underfoot. A television is positioned on a stand opposite the seating, and large windows allow for ample natural light.

Guest suite in Bloomfield

4.98 out of 5 average rating, 253 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

A modern kitchen is visible, featuring dark cabinetry and granite countertops. Stainless steel appliances, including a stove and dishwasher, are present. The open layout offers a view into the living area with natural light coming from a nearby window, complementing the spacious feel of the room.

Apartment in Bloomfield

4.75 out of 5 average rating, 308 reviews

Apt 9 Bloomfield / Lawrenceville small private 1br

This small 1 bedroom is a clean, cool place to stay. Located in one of the best spots for work or play. Freshly remodeled & Fully furnished with queen bed, full bathroom, smart HDTV, free wifi, cable. Place is close to the city center, art and culture, nightlife, public transport and parks. You would love the location, the coziness. The apartment has a full kitchen with all needed essentials.

Superhost

A spacious living area is shown, featuring a bright orange sofa paired with pillows and a light blue armchair. A low wooden coffee table sits on a patterned area rug, and a potted plant is positioned beside a wall-mounted television. Warm lighting enhances the inviting ambiance.

Apartment in Pittsburgh

4.84 out of 5 average rating, 550 reviews

Renovated top floor unit! Close to downtown!

Bright, completely renovated, top floor unit in an historical neighborhood of Pittsburgh! Close enough to walk to the both Heinz Field and PNC Park stadiums, and Rivers Casino. Lot's of charm and character! Located 5-10 minutes from downtown and convention center via car, or take the bus right from the corner. Please note this is a third floor walk up, so please be comfortable with steps!

Top guest favorite

A cozy living area features a comfortable gray sofa adorned with patterned throw pillows. A wooden coffee table sits in front of the sofa, and a small dining table with a chair is positioned nearby. A kitchenette is visible, highlighted by textured stone and retro appliances.

Cottage in Glenshaw

4.94 out of 5 average rating, 433 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.