Family-friendly vacation rentals in Shadyside, Pittsburgh

4.78 out of 5 average rating, 656 reviews

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

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.

Apartment in South Side Flats

A spacious living area features a navy blue couch and a large coffee table on a decorative area rug. Two lamps provide soft lighting, while a mirrored accent wall enhances the room's openness. The dining area is visible in the background, with a large table and chairs.

4.85 out of 5 average rating, 740 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.

4.98 out of 5 average rating, 198 reviews

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

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, 321 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.

A spacious front porch features a swing and chairs for relaxation, framed by lush greenery and colorful plantings. A vibrant outdoor hammock adds a playful touch. The area is supported by sturdy columns and showcases a well-maintained yard, providing a welcoming entrance.

4.95 out of 5 average rating, 278 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 suite in Highland Park

A well-decorated sleeping area features a vibrant blue quilt atop the spacious bed, accented by decorative pillows. A table lamp with a stained glass shade provides warm lighting. Artwork adorns the walls, and a small TV is positioned on a wooden stand nearby.

4.85 out of 5 average rating, 227 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!

A cozy bedroom features a spacious bed with a yellow and gray bedding set. Natural light enters through two large windows. A nightstand with a lamp is positioned beside the bed, and a decorative plant adds a touch of greenery. A door leads to additional space.

4.84 out of 5 average rating, 399 reviews

Uptown Apartment - right up from Pittsburgh!

**PLEASE BE HONEST ABOUT THE NUMBER OF GUESTS** *Pets are welcome! One time $40 pet fee* Uptown is a mixed residential & commercial area that’s right up from downtown Pittsburgh! It’s up and coming, a unique neighborhood that has all the benefits of being near the heart of the city! The apartment is close to the city center, art and culture, and public transport. You’ll love my place because of the location, coziness, and cleanliness. All types of travelers welcome!

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.

4.97 out of 5 average rating, 421 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 favorite

A modern living area features a kitchenette with a small refrigerator and microwave, alongside a comfortable white chair and a sleek gray sofa. A wall-mounted TV displays a city skyline, while exposed brick adds a touch of character. Natural light filters in through a window.

Home in Bloomfield

4.88 out of 5 average rating, 503 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).

The exterior of a historic Queen Anne Victorian home is captured, featuring a multicolored façade with green and red accents. A spacious covered porch is visible, furnished with chairs and a table. Colorful flowerbeds with blooming daffodils line the front yard, framed by a large grassy area.

4.92 out of 5 average rating, 439 reviews

Historic Charmer | Spacious | Off Street Parking

Charming 2-Bedroom Apartment in Historic Victorian Home Bright and inviting second-floor unit in an 1887 Queen Anne Victorian. Features a private entrance, staircase, and deck with stunning views of the Ohio River and Emsworth Lock and Dam. Just 6 miles from Heinz Field, PNC Park, and 15 miles from Pittsburgh International Airport. One block from public transportation. Set on a spacious lot with gardens, fruit trees, and a magnificent oak tree.

Guest suite in Bloomfield

The exterior of a historic Colonial Revival house is presented, featuring a covered front porch with decorative columns and a wooden railing. Lush greenery and flowering plants border the walkway leading to the entrance, while trees provide shade in the background.

4.98 out of 5 average rating, 254 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.