Family-friendly holiday rentals in Shadyside

4.97 out of 5 average rating, 148 reviews

The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.

Flat in East Liberty

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

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.

4.78 out of 5 average rating, 694 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.

Guest suite in Highland Park

The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.

4.98 out of 5 average rating, 292 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

A light-filled living area displays a comfortable sofa paired with an accent chair and a round coffee table. A dining area with bar stools is visible, along with a modern kitchen featuring stainless steel appliances and stylish cabinetry. Warm wooden flooring adds to the inviting ambiance.

4.9 out of 5 average rating, 205 reviews

Cozy King Suite with Parking!

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

4.98 out of 5 average rating, 171 reviews

The image showcases a three-story home with a light grey exterior and blue accents, featuring a prominent gabled roof. A wooden deck with a railing extends in front, providing an inviting entryway. The neighborhood architecture is visible in the background.

Flat in Pittsburgh

Cute Apt Minutes from Downtown and Stadiums!

🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

4.92 out of 5 average rating, 211 reviews

The bedroom features a spacious bed with white bedding and multiple patterned throw pillows. Natural light filters through the large windows, enhancing the warm wooden floors. A decorative wall separates the bedroom from the living area, while shelves provide additional storage.

Home in Bloomfield

Urban serenity, privacy in charming carriage house

Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

The living room features a spacious gray sectional sofa positioned near large windows that allow natural light to fill the space. A modern glass coffee table is centered on a soft area rug, while white interior doors provide access to closet space.

4.89 out of 5 average rating, 213 reviews

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

The spacious bedroom features a wooden platform bed with a plush mattress and white linens, complemented by a decorative blanket. A minimalist bedside table holds a lamp, while two framed botanical prints adorn the wall. Natural light filters through the window, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 146 reviews

Shadyside/Pittsburgh, Modern & Cozy 1BD w/Prkng

Modern and family oriented 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 Bedroom & Dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

A modern living area features a light grey sectional sofa draped with a vibrant orange throw. Colorful artwork adorns the wall above a sleek television, while a spiral staircase provides access to the upper levels. A dining area with pink chairs is visible in the background.

4.99 out of 5 average rating, 160 reviews

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

4.91 out of 5 average rating, 138 reviews

An inviting outdoor patio features a circular fire pit surrounded by cozy seating arrangements. Bamboo plants add a touch of greenery, while a white wooden fence provides privacy. The space is designed for relaxation and social gatherings.

Home in Bloomfield

Fire Pit + Family Friendly + Great Location!

Welcome to our family-friendly home in Bloomfield! Tickle the ivories on our baby brand piano while you send the kids upstairs to play with coloring books, toys, and more. Cook a great meal in our well stocked kitchen, or relax on the couch and watch Netflix. At night, spark up the fireplace and enjoy an evening outside with friends! If you're an "out and about" type - you're just a few blocks from the main drag in Bloomfield, full of great bars & restaurants!

4.83 out of 5 average rating, 257 reviews

A spacious bed is positioned against a white wall, featuring neutral bedding and decorative pillows. Two modern bedside lamps provide soft lighting. To the left, a sleek sleeper sofa complements the minimalist design of the room.

Flat in Friendship

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

This Bright basement studio is for anyone needing a stylish, clean place to stay while visiting Pittsburgh. It has a new queen bed, sleeper sofa, desk, bar and a very large bathroom. It has a private entrance at the back of a beautiful 1890s Pittsburgh mansion. It works very well for travelers 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 suite in Bloomfield

A cozy bedroom features a spacious bed dressed in an orange quilt. Two windows allow natural light to fill the room, and a colorful chair sits beside a small nightstand. A decorative fireplace adds character, complemented by framed artwork hanging above.

4.98 out of 5 average rating, 217 reviews

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Popular amenities for Shadyside family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 121 reviews

A spacious kitchen features modern appliances, including a stove and microwave, set against a backdrop of exposed brick. Ample counter space is provided by a mix of polished stone and wood surfaces, with an undermount sink positioned for convenience.

Loft in Allegheny West

"The Spa Room" Renovated Flashlight Factory

4.87 out of 5 average rating, 644 reviews

A modern living area features a white sectional sofa with colorful cushions, complemented by a sleek glass coffee table. A vibrant piece of wall art adds visual interest, while a tall plant brings a touch of greenery. Warm wood flooring enhances the inviting atmosphere.

Flat in Brighton Heights

420 friendly Luxury loft apt w jet tub & balcony

4.95 out of 5 average rating, 113 reviews

An outdoor space is illuminated by soft string lights, featuring a hot tub surrounded by wooden decking. A gazebo with seating is nearby, and a fire pit is visible in the background, complemented by lush greenery and trees that create a private setting.

Home in Pittsburgh

Secluded Hilltop Hideaway~Hot Tub~Two Living Rooms

4.83 out of 5 average rating, 199 reviews

A modern shower area features sleek gray and white tiles, accented by a rainfall showerhead and multiple body sprays. A recessed shelving unit displays neatly rolled towels and toiletries, providing convenient storage. Soft lighting adds a serene ambiance to the space.

Home in Duquesne Heights

Mountain Retreat in the Heart of the City

Flat in Upper Lawrenceville

A private hot tub filled with bubbling water is set against a backdrop of wooden fencing. Nearby, a cozy seating area is arranged with blue cushions and a low table, providing a space for relaxation and enjoyment.

4.95 out of 5 average rating, 282 reviews

Hot Tub | Light & Bright w/Deck | Walk to Butler!

4.94 out of 5 average rating, 156 reviews

Home in Deutschtown

HotTub/Firepit/Parking! Less than 1mi PNC Park

Home in South Side Slopes

A private hot tub is nestled in an outdoor area, surrounded by softly glowing string lights and lush potted plants. Wooden steps lead to an elevated deck, creating an inviting space for relaxation and enjoyment during any season.

4.97 out of 5 average rating, 314 reviews

Gorgeous Southside slopes house w/outdoor hot tub

Home in Squirrel Hill North

An outdoor patio features a wooden pergola overhead with dining chairs and a table. Surrounding greenery includes colorful trees in autumn hues and blooming daffodils. The stone pathway guides the view towards a cozy seating area with Adirondack chairs, creating an inviting space for relaxation.

4.93 out of 5 average rating, 193 reviews

hot tub fire pit Art & Wellness Retreat

Family- and pet-friendly home rentals

5 out of 5 average rating, 126 reviews

A spacious living area features a comfortable sectional sofa and a pair of armchairs, accented by soft seating cushions. Large windows are adorned with sheer curtains, allowing natural light to brighten the room. A decorative area rug lies on the hardwood floor, and small tables complete the arrangement.

Home in Pittsburgh

Seneca Place: A historic home in Mount Lebanon.

4.82 out of 5 average rating, 425 reviews

The living area features a fold-out sofa adorned with a colorful floral cover, accompanied by two upholstered chairs and a wooden writing desk. A rectangular coffee table sits at the center, with light streaming in through large windows that enhance the space's brightness.

Flat in Deutschtown

1 Bed, idyllic, stadiums, free parking, & Pets OK

4.96 out of 5 average rating, 130 reviews

A spacious living area is presented with a light-colored sectional sofa and a black coffee table atop a striped rug. A mounted television is visible above an elegant fireplace. Adjacent, a dining area features a round table with four chairs, illuminated by a stylish light fixture.

Flat in Pittsburgh

Cozy 2 bedrooms unit - 10 minutes to Downtown

4.94 out of 5 average rating, 16 reviews

A charming house exterior is shown, featuring a welcoming porch with seating, surrounded by well-maintained landscaping. Nearby, a private driveway provides ample parking space. The modern kitchen is highlighted, showcasing stainless steel appliances, sleek countertops, and ample storage. A cozy living room is displayed with a tasteful arrangement, centered around a fireplace.

Home in Garfield

BRAND NEW, Private Parking, Stylish 3bedroom house

Home in East Carson Street

A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.

4.91 out of 5 average rating, 422 reviews

Urban converted gas station in heart of South Side

4.97 out of 5 average rating, 145 reviews

A bright bedroom features a spacious bed adorned with a patterned throw and decorative pillows. Soft lighting from two bedside lamps enhances the atmosphere. A large window with sheer curtains provides natural light, and a wall displays a friendly animal portrait complemented by hanging greenery.

Home in Troy Hill

The View*Sleeps 6* City Home

Flat in Lower Lawrenceville

A cozy bedroom features a queen bed adorned with plush pillows and a casual blanket. A contemporary dresser sits against a wall, while a television is mounted nearby. A decorative plant adds a touch of greenery, enhancing the space's inviting ambiance.

4.87 out of 5 average rating, 109 reviews

Pet Friendly, Butler St. Apt w/Private Entrance

Guest suite in Stanton Heights

A light-filled living area features a grey sofa, accented by decorative pillows. A wooden coffee table is positioned in front, displaying a book. The wall showcases a world map, while a blue door and kitchenette are visible in the background.

4.96 out of 5 average rating, 142 reviews

Newly renovated 1brm studio. Close to everything!

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 22 reviews

A cozy stone patio is covered with a grape arbor, offering shade and inviting seating arrangements. A small table adorned with flowers is surrounded by chairs, while potted plants and greenery add to the serene outdoor setting. The area is easily accessible and well-maintained.

Flat in Pittsburgh

1st Fl. Huge Flat on 2 Acres - Pets/Garage Parking

Home in Pittsburgh

5 out of 5 average rating, 4 reviews

Posh Pittsburgh ~ 2-story luxury suite & patio

5 out of 5 average rating, 5 reviews

A private patio area features a paved surface with scattered leaves, leading to a grassy lawn edged by trees. A chair is positioned nearby, offering a spot to enjoy the outdoor space.

Home in Oakmont

Convenient townhome

4.8 out of 5 average rating, 86 reviews

A wooden dining table is positioned in the foreground, featuring a decorative orange fish centerpiece. The background reveals a modern kitchen with sleek granite countertops and a stylish backsplash, complemented by an overhead stainless steel range hood.

Home in Beechview

Renovated Cozy Duplex w/pool, Close to downtown

5 out of 5 average rating, 42 reviews

A newly renovated pool area features a sparkling blue pool surrounded by a spacious patio. Comfortable lounge chairs are positioned along the edge, with trees and a privacy fence providing a secluded setting. A pool house is visible in the background against a colorful sky.

Home in Coraopolis

PIT Staycation Retreat with Pool House!