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Family-friendly holiday rentals in Wilkinsburg

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Wilkinsburg

  • Total holiday rentals

    Explore 30 holiday rentals in Wilkinsburg

  • Nightly prices starting at

    Wilkinsburg holiday rentals start at $85 NZD per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Wilkinsburg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wilkinsburg rentals

  • 4.7 Average rating

    Wilkinsburg stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Wilkinsburg

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

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Top Guest favourite
A cozy living room area showcases a brown leather sofa adorned with decorative pillows. Two lamps illuminate the space, and a round coffee table is positioned in front of the sofa. Artwork is displayed on the walls, contributing to the classic decor.
Apartment in Pittsburgh

2BR Apt. /Pittsburgh/East/Regent Square/Frick Park

First floor 2-bedroom apartment with classic decor. Modern bath/kitchen with complete utensils. Wi-Fi & wired gigabit network. Two TVs with service. Appropriate for business traveler, families with older children. Living and dining room accommodates 8-10 people. Convenient to downtown, Oakland/universities. Across street parking. Nearby restaurant/stores and park in walking distance. Open bar. No per-person or amenities charges. Virtual tour at https://my.matterport.com/show/?m=BFeAkSV4ekM

KitchenIndoor spacesParking

4.99 out of 5 average rating, 129 reviews
Superhost
A cozy living area features a colorful array of artwork on the walls and a mounted flat-screen television. A decorative fireplace with a warm glow is complemented by a cowhide rug on the wooden floor. A leather recliner and a dining area are seen in the background.
Home in Pittsburgh

Steel City Beds, Breakfast and More

3-story single family home in Pittsburgh's popular eastend. Common areas decorated with eclectic mix of outsider and emerging art, art deco collectibles and antiques. Inviting outdoor spaces including front porch, fenced in backyard and play area good for kids and pets. Short walk to public transit, coffee shops, fine-dining, food coop, Construction Junction architectural artifacts, historic Frick Mansion and more. 5 minute drive or Uber ride to 4 premier shopping and entertainment centers.

KitchenIndoor spacesComfort

4.81 out of 5 average rating, 255 reviews
Superhost
A rustic single-story ranch home is set against a backdrop of trees. The brick exterior is complemented by a shaded porch, with steps leading up from a grassy area. A wooden railing can be seen near the entrance, while some construction materials are visible nearby.
Apartment in Pittsburgh

City-Adjacent Wooded Retreat - Peace and Wildlife

1950’s Ranch on secluded road. No other spot has so much access to private forest, this close to the city! Take a stroll, build a fire or enjoy a sunset from the porch. Only :10 from hotspots like Shadyside and L-Ville. :15-:20 from UPMC Oakland. Full & twin beds. Sparse furniture, w/ cooking utensils included. This isn’t a hotel room, it’s a home in transition and we invite you to stay simply, easily & cheap! I live close by for help in town or for anything you might need during your stay.

Indoor spacesKitchenPets

4.84 out of 5 average rating, 131 reviews
Top Guest favourite
The floating home is presented from an aerial view, showcasing its unique two-level structure nestled on the calm waters of the Allegheny River. The wrap-around deck and patio doors are visible, enhancing the connection to nature, with lush greenery lining the riverbank.
Houseboat in Blawnox

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

FamilyIndoor spacesComfort

4.99 out of 5 average rating, 109 reviews
Top Guest favourite
An outdoor patio area features a covered pavilion with a colorful mural on the wall. A round table surrounded by black metal chairs is situated on the tiled surface, with greenery and flower beds enhancing the space. Shade is provided by a large tree nearby.
Apartment in Pittsburgh

Secret Garden by Frick Park with Garage Parking

Disappear into the secret garden of this unique centrally located apartment a few blocks from Frick Park. Steps from Regent Square, a short walk to Point Breeze, close to universities, hospitals, Oakland, Bakery Square, and Rockwell Park. Easy access to 376 Parkway, and 10 to 15 min to downtown. 15 min from Monroeville. This listing is great for anyone who wants some peace and quiet at the end of the day. Located on a dead end street there is little traffic noise to interrupt your relaxation.

Indoor spacesFamilyCheck-in

4.96 out of 5 average rating, 104 reviews
Guest favourite
A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.
Home in Shadyside

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

KitchenFamilyAccess

4.98 out of 5 average rating, 113 reviews
Guest favourite
Apartment in East Liberty

Spacious 2BR Steps to WholeFoods

Brand new construction, high end spacious 2 bedroom with designated off street parking! Double King Suites and Full Size pullout bed offer enough room for the whole family Enjoy the convenience of being across the street from WholeFoods & steps to dozens of restaurants & shops, short Walk to UPMC Shadyside, West Penn, & Children's hospitals, close CMU & Pitt! Enjoy dozens of restaurants shops and coffee shops just a walk away! Fully stocked for both long and short term stays!

FamilyIndoor spacesAmenities

4.96 out of 5 average rating, 228 reviews
Guest favourite
The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.
Apartment in Pittsburgh

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

KitchenFamilyAmenities

4.91 out of 5 average rating, 556 reviews
Guest favourite
A serene bedroom features a cozy bed with a bright yellow and blue blanket, accented by decorative pillows. A pair of bedside tables with lamps flank the bed, while a framed fox artwork hangs above, contributing to the room's inviting ambiance.
Condo in Pittsburgh

A Fresh Mid Century 2- bedroom East End Area

A fresh Mid Century Condo that pays tribute to the 1950's in Pittsburgh. A fully remodeled first floor 2-bedroom unit in a 6 unit Condo. Large windows and shaded back porch overlooking courtyard. Close to many local restaurants, bars, cafes, and the bus line. Near Frick Park! Free parking space. Easy access to local universities (Pitt, CMU, Duquense), East Liberty, Squirrel Hill, Oakland, South Side, downtown and the stadium district. Minutes away from Parkway (376).

Indoor spacesKitchenAccess

4.93 out of 5 average rating, 177 reviews
Top Guest favourite
Apartment in Forest Hills

Pittsburgh Area 2 Bedroom Apt.

Comfortable, Convenient & Clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Free off street parking. Downtown & Stadiums 10 mi. Universities, Medical Center, PPG Paints Arena & Carnegie Museums 8 mi. Kennywood Amusement Park, Monroeville Convention Center & Sri Venkateswara Temple 5 mi. I-76 PA Turnpike 8mi. International A/P 27 mi.

Indoor spacesKitchenBreakfast

4.99 out of 5 average rating, 196 reviews
Top Guest favourite
The living room features a spacious grey sofa adorned with a navy throw blanket. A blue and cream patterned rug covers the hardwood floor, while natural light streams through sheer white curtains. A light fixture and a small side table complete the serene ambiance.
Apartment in Pittsburgh

Newly remodeled 2 bedroom apartment

Newly remodeled 2 bedroom apartment on the first floor of a duplex located in a quiet neighborhood. Fully equipped kitchen. Roku Tv with cable and free wifi. Plenty of on street parking. Walking distance to Frick Park and great neighborhood bars/ restaurants. Under one mile to Regent Square bars and restaurants. Just a few minute car ride to the heart of Squirrel Hill. Under ten minute car ride to downtown Pittsburgh. Self check-in.

FamilyIndoor spacesNearby

4.95 out of 5 average rating, 173 reviews
Top Guest favourite
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.
Apartment in Squirrel Hill North

Spacious, warm, private apartment near CMU /Pitt

Spacious, warm, private apartment with parking set in a beautiful, quiet, family neighborhood. Just minutes away walking from CMU (10 Min) and Pitt 20 Min). And a 4 minute walk Bus stop (61xx) to all of Pittsburgh. Shadyside, Squirrel Hill and the Carnegie museums are in the immediate neighborhood with great options for dining and entertainment. Also the Phipps Conservatory and Botanical Gardens are only 1.3 Miles from the house.

Indoor spacesKitchenCondition

4.97 out of 5 average rating, 921 reviews

Popular amenities for Wilkinsburg family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
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.
Home in Squirrel Hill North

hot tub fire pit Art & Wellness Retreat

Indoor spacesKitchenLocation

4.92 out of 5 average rating, 208 reviews
Guest favourite
A richly decorated hallway is highlighted by wooden paneling and intricate ceiling details. Colorful artwork adorns the walls, including a prominent painting of a seated figure. A small table, accented with vibrant decor, contributes to the warm ambiance of the space.
Guesthouse in Pittsburgh

Luxury: Pointe Brise Retreat House

Indoor spacesKitchenGetting around

4.88 out of 5 average rating, 128 reviews
Guest favourite
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

Serene Secluded Hilltop Hideaway. Hot Tub Fire Pit

KitchenFamilyQuiet

4.95 out of 5 average rating, 132 reviews
Guest favourite
Home in North Side

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

Indoor spacesFamilyBackyard

4.94 out of 5 average rating, 197 reviews
Top Guest favourite
The image captures a serene outdoor space featuring a pond with cascading water and lush greenery. A wooden pergola provides shade over hanging chairs. The landscaped area includes rocks, plants, and a glimpse of the home in the background, enhancing the tranquil atmosphere.
Home in North Side

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 136 reviews
Guest favourite
An inviting private hot tub is situated in a fenced backyard area, surrounded by soft lighting and decorative plants. The brick wall of the house provides a rustic backdrop, creating a cozy ambiance at dusk.
Townhouse in Pittsburgh

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

Indoor spacesFamilyBiking

4.93 out of 5 average rating, 427 reviews
Superhost
Home in North Side

Hot Tub | 2 King Beds | Parking | Family Friendly

FamilyIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 226 reviews
Guest favourite
A six-person hot tub is set in a private outdoor area, surrounded by a white wooden fence. Gentle water jets create ripples in the clear blue water. Potted ferns hang from the fence, adding a touch of greenery to the tranquil space.
Home in South Side Flats

Pittsburgh's Tropicana w/ outdoor hot tub

Indoor spacesFamilyHiking

4.97 out of 5 average rating, 197 reviews

Family- and pet-friendly home rentals

Guest favourite
The bedroom features a spacious bed covered in crisp white linens, highlighted by a blue accent throw. Blue curtains frame multiple windows, allowing natural light to fill the room. A small desk and chair are positioned nearby, complemented by a decorative plant and wall art.
Apartment in East Liberty

Upscale King Bed Suite |ADA w/ Free parking!

FamilyIndoor spacesLaundry

4.97 out of 5 average rating, 229 reviews
Top Guest favourite
Townhouse in Mt. Lebanon

Private Mt Lebanon Retreat Near Airport/Downtown

FamilyKitchenAccuracy

4.99 out of 5 average rating, 187 reviews
Guest favourite
The cabin exterior is seen surrounded by lush greenery. A small outdoor dining area features a table and four chairs under a yellow umbrella. A portion of the cabin façade is visible with wooden logs, while a stone fire pit can be seen in the foreground.
Cabin in Pittsburgh

Cabin in Pittsburgh. 20 minutes to Pittsburgh

FamilyIndoor spacesAccess

4.91 out of 5 average rating, 179 reviews
Superhost
An open-concept living area features a large green sectional sofa with textured cushions, inviting relaxation. A bold black and white patterned area rug anchors the space, complemented by a modern chandelier. Natural light floods in through the windows, enhancing the cozy atmosphere.
Home in Pittsburgh

Pet Friendly Pittsburgh Home Near Zoo, Sleeps 12

FamilyIndoor spacesNearby

4.84 out of 5 average rating, 127 reviews
Guest favourite
A light-filled living area features a spacious sectional sofa and a coffee table, complemented by decorative pillows and soft furnishings. A wall clock indicates the time, while a dining space with a wooden table is visible in the background, enhancing the open layout.
Townhouse in Pittsburgh

Spacious 3BR Retreat! Fire Pit & Free Parking!

KitchenFamilyWalkability

4.86 out of 5 average rating, 283 reviews
Guest favourite
A modern living room features large windows that allow natural light to fill the space. A sleek gas fireplace is framed by dark stone, while a large television is mounted on the wall. Comfortable armchairs and a circular coffee table complete the inviting atmosphere.
Home in Strip District

Skyline Haven:5BR/3.5BA +2 parking spots + Rooftop

FamilyIndoor spacesValue

4.95 out of 5 average rating, 179 reviews
Guest favourite
A spacious living area features a dark couch paired with a rustic wooden coffee table. A dining table with wooden chairs sits nearby, illuminated by natural light from two large windows. Decorative wall art and a large mirror enhance the room's aesthetic.
Home in Monroeville

3 Bedroom Pittsburgh Neighbor - Pets

Indoor spacesFamilyValue

4.83 out of 5 average rating, 160 reviews
Guest favourite
A tree-lined pathway leads to a stone entrance, bordered by lush greenery. A decorative bench offers a resting spot, while the natural landscaping includes small shrubs and ground cover. The setting provides a calm entrance into the home, surrounded by a relaxed outdoor atmosphere.
Home in Pittsburgh

The Stone House

Indoor spacesFamilyAccess

4.87 out of 5 average rating, 84 reviews

Family-friendly home rentals with a pool

Superhost
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 Dormont

Renovated Cozy Duplex w/pool, Close to downtown

FamilyIndoor spacesTV

4.81 out of 5 average rating, 105 reviews
Guest favourite
A large in-ground heated pool is showcased within a shaded outdoor area. Tall trees provide natural privacy, while bright blue waters reflect the clear sky. Lounge chairs are positioned along the edge of the pool, inviting relaxation in a serene setting.
Home in Monroeville

Mayberry Escape

Indoor spacesFamilyComfort

4.87 out of 5 average rating, 197 reviews
Superhost
Home in Highland Park

Urban Pittsburgh Home w/ Pool

Indoor spacesKitchenAccuracy

4.78 out of 5 average rating, 112 reviews
Superhost
Home in Pittsburgh

A beautiful cozy home away from home!

Indoor spacesKitchenHospitality

4.67 out of 5 average rating, 18 reviews
Superhost
A private pool glistens in a vibrant blue, surrounded by a spacious deck. Lounge chairs with orange cushions are placed nearby, and a shaded seating area is visible under a large umbrella. Lush greenery and tiered wooden decking create a tranquil outdoor atmosphere.
Home in Brookline

Heated Pool Oasis • Free Parking • 5 min to PGH

Indoor spacesFamilyBackyard

4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Pittsburgh

Relax in a 3bd & loft w/Pool in Plum PA

FamilyKitchenSleep quality

4.88 out of 5 average rating, 59 reviews
Guest favourite
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

Sleep qualityHospitalityValue

4.91 out of 5 average rating, 23 reviews
Guest favourite
Apartment in North Side

FIDO PLUS TWO 1.5 miles to Acrisure Stadium

Check-inDecorPets

4.92 out of 5 average rating, 13 reviews

When is the best time to visit Wilkinsburg?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$187 NZD$204 NZD$202 NZD$324 NZD$287 NZD$297 NZD$244 NZD$212 NZD$212 NZD$270 NZD$287 NZD$241 NZD
Avg. temp-2°C0°C4°C11°C16°C21°C23°C22°C18°C12°C6°C1°C

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