Family-friendly vacation rentals in Shadyside

Apartment in East Liberty

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.

4.97 out of 5 average rating, 146 reviews

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.

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, 275 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.

The living room features a large sectional couch in a neutral hue, positioned around a low coffee table. A window covered with vertical blinds allows natural light to enter, and an air conditioning unit is situated nearby. The floor has a wood-like finish, adding warmth to the space.

4.77 out of 5 average rating, 573 reviews

Quaint cozy Shadyside One Bedroom

Cozy apartment located in Shadyside.Just steps away from Shadyside Hospital, this apartment is great for long or short term visitors.Grocery stores, restaurants, bars, and shops are all just a few minute walk from this apartment as well. The apartment is a short drive to Heinz Field, PPG Paints Arena, PNC Park, and all the amazing museums Pittsburgh has to offer! Also near by is CMU, PITT, Chatham Univeristy, and Carlow College.Free parking & WiFi.Towels,bed linens,toilet paper provided.

4.92 out of 5 average rating, 209 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.

A modern bedroom is characterized by sloped wooden ceilings and exposed beams. A spacious bed with a light gray coverlet is centered against the wall, flanked by two bedside tables with lamps. Natural light enters through a small window, illuminating the wooden floor.

4.88 out of 5 average rating, 225 reviews

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

Unique and family oriented modern 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 spacious bedroom features a large bed with crisp white linens and plush pillows against a navy blue accent wall. A small wooden bedside table holds a lamp, and a piece of artwork depicting mountains adorns the wall. Soft natural light enters through a window with light curtains.

4.82 out of 5 average rating, 304 reviews

Chic & Cozy 2BR | Walkable Shadyside Location

Fresh 2 BR apartment in the heart of Shadyside! Prime location, steps from UPMC Shadyside & Walnut Street! Fully equipped for either a long or short stay! 🌟King Bed (Memory foam mattress) ⭐️Queen Bed (Memory foam mattress) 🌟Pet friendly! ⭐️Central AC/ Heat 🌟Fully stocked & equipped kitchen ⭐️Luxurious waterfall shower head 🌟Two Smart TVs ⭐️Free Street parking 🌟Laundry (Shared & Free) ⭐️Pull out bed (Full) 🔥Message today to secure your reservation!🔥

4.84 out of 5 average rating, 240 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.

Apartment 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).

4.96 out of 5 average rating, 344 reviews

A bright kitchen space is shown, featuring modern cabinetry and stainless steel appliances. A central island with seating for four is highlighted, complemented by a stylish pendant light above. Natural light streams in through a nearby window, enhancing the clean, inviting atmosphere.

Apartment in Bloomfield

Cozy Entire APT B Friendship Park & Free Parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

Apartment in Lower Lawrenceville

The living area features a comfortable couch and a coffee table, with a wall of windows allowing natural light to fill the space. A desk and chair are positioned for workspace, while decorative elements and plants add a homely touch.

4.92 out of 5 average rating, 122 reviews

Pet Friendly with King Bed on Butler Street!

Located right in the heart of Lawrenceville on Butler St., you can't beat this location! Our 1st floor apartment is tastefully furnished and stocked for short term and longer term stays - perfect for living and working, or quick getaways! Our well appointed kitchen is great for cooking, our two desks are perfect for two work from home travelers, our cozy bedroom invites you to sleep in, and the living room's couch and smart TV invite you to relax!

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, 207 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.

An open-concept living area features a modern kitchen with white cabinetry and granite countertops. A comfortable sofa sits in front of a coffee table, while a mounted flat-screen television displays various streaming options. Soft lighting is provided by a ceiling fan and recessed lighting.

4.91 out of 5 average rating, 110 reviews

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

A spacious living area features a large sectional sofa adorned with a textured throw, complemented by a wooden coffee table. A 70-inch smart TV is mounted on the wall, while a small decorative plant and a cozy chair add a touch of warmth to the space.

4.96 out of 5 average rating, 159 reviews

Shadyside King Suite w/ Parking!

Stylish 1BR/1 bath apartment with off street parking in the heart of Shadyside, steps to Walnut St -- DESIGNATED OFF STREET PARKING! Short Walk to UPMC & West Penn hospitals, close to CMU & Pitt! The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit, 70inch 4K TV!

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, 118 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

Apartment in Brighton Heights

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.

4.87 out of 5 average rating, 635 reviews

420 friendly Luxury loft apt w jet tub & balcony

4.92 out of 5 average rating, 106 reviews

A collage features a cozy living room with stylish furniture and artwork, a fenced backyard with a hot tub and outdoor seating, a traditional blue house exterior, and a modern kitchen showcasing stainless steel appliances and ample counter space.

Home in Manchester

NEW! Luxurious 5bdr w/ a hot tub. Walk to stadiums

4.88 out of 5 average rating, 224 reviews

An open concept kitchen and dining area features light hardwood flooring and white brick walls. A round wooden dining table is set with plates and utensils, surrounded by four light-colored chairs. Two bar stools are positioned at a kitchen counter in the background, alongside modern appliances.

Townhouse in Bloomfield

HOT TUB KING bed Luxurious 2 bed in PRIME location

4.84 out of 5 average rating, 189 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

4.96 out of 5 average rating, 140 reviews

Home in East Allegheny

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

Townhouse 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.

4.97 out of 5 average rating, 268 reviews

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

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, 311 reviews

Gorgeous Southside slopes house w/outdoor hot tub

Family- and pet-friendly home rentals

4.91 out of 5 average rating, 252 reviews

A cozy living area is highlighted by a sleek beige leather sofa, accompanied by decorative pillows. A glass coffee table sits on an ornate area rug, while natural light illuminates the space. The staircase and a softly lit hallway can be seen in the background.

Home in Duquesne

Entire home near Kennywood without extra fees.

4.94 out of 5 average rating, 374 reviews

The living area features a green velvet sofa and a neutral-colored couch, arranged around a rectangular white coffee table. A minimalist rug lies on the floor, while a flat-screen TV is mounted on the wall. Natural light filters through the curtains, illuminating the space.

Home in Carrick

Large house to relax with friends and family

4.87 out of 5 average rating, 324 reviews

A modern living area features a spacious sofa and a glass coffee table, complemented by a decorative area rug. Large windows allow natural light to fill the space, while a well-equipped kitchen is visible in the background with stainless steel appliances.

Apartment in Pittsburgh

Cozy + Modern apartment near the city!

4.83 out of 5 average rating, 316 reviews

A modern kitchen features white cabinetry and wooden countertops, along with stainless steel appliances. Natural light illuminates the space from large windows. Open shelving displays dishware and decorative items, while a coffee maker and kettle are arranged on the countertop.

Home in East Allegheny

Farmhouse Design + Fire Pit in Heart of Pittsburgh

Apartment in Squirrel Hill North

A well-equipped kitchen is highlighted by modern appliances, including an oven and a refrigerator. A wooden dining table with four chairs offers a space for meals. Natural light floods the area through large glass doors leading to an outdoor patio.

4.97 out of 5 average rating, 844 reviews

Spacious, warm, private apartment near CMU /Pitt

4.89 out of 5 average rating, 129 reviews

The living area features high ceilings with natural light streaming through large windows. A modern sofa is paired with two round coffee tables placed on a patterned area rug. Vibrant wall art adds character to the space, enhancing the industrial aesthetic.

Loft in North Oakland

Industrial Loft 5 min to Children’s Hospital, slps

Apartment in East Allegheny

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.

4.82 out of 5 average rating, 409 reviews

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

4.9 out of 5 average rating, 191 reviews

A bright kitchen area is furnished with modern white cabinetry and a granite countertop. The kitchen features a decorative tile backsplash and a large window, allowing ample natural light. A wooden dining table with stools is positioned in the center, enhancing the open layout.

Loft in Strip District

Lovely Strip District loft with free parking

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 19 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.

Apartment in Pittsburgh

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

The studio features a queen bed with light bedding, complemented by a bedside table. A cozy seating area includes a blue sofa and a TV stand with a television. Two large windows provide natural light, adorned with horizontal blinds.

Apartment in Lower Lawrenceville

4.58 out of 5 average rating, 66 reviews

CozySuites | Modern SDO, Lawrenceville

A modern kitchen is presented with gray cabinetry and a clean countertop. Stainless steel appliances include a refrigerator, microwave, and stove. A silver sink is visible, positioned near a soap dispenser, while vibrant light illuminates the space.

Apartment in Northshore

4.75 out of 5 average rating, 4 reviews

Downtown Pittsburgh

5 out of 5 average rating, 4 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

4.79 out of 5 average rating, 82 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

4.92 out of 5 average rating, 24 reviews

A serene bedroom features a spacious bed dressed in white linens and a yellow striped throw. A decorative pillow adds a touch of texture. A bedside lamp provides soft illumination, complementing the floral artwork displayed above the bed.

Apartment in Monroeville

Monroeville Bella

4.97 out of 5 average rating, 68 reviews

The living room features vaulted ceilings and large windows, allowing natural light to fill the space. Comfortable leather seating is arranged around a rustic coffee table, with a modern entertainment unit and a fireplace in the background, enhancing the inviting ambiance.

Townhouse in Bridgeville

20 mins to Downtown- pool table & fenced yard