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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 $88 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, Wi-Fi 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

Indoor spacesFamilyAccess

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.

Indoor spacesKitchenBackyard

4.81 out of 5 average rating, 255 reviews
Guest favourite
The spacious living area features a mix of modern and cozy furnishings. A large sectional sofa and additional seating surround a circular coffee table, with a textured area rug underfoot. Exposed brick adds character, while large windows allow natural light to fill the room.
Apartment in Shadyside

Huge Open Concept 2BR by Walnut

HUGE apartment In the heart of Shadyside w/ room for the whole family! 1 Block to Walnut St & FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 2 floor apt in a prime location, w/ all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, & fitness studios close by. The building was gutted & remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances is brand new!

Indoor spacesFamilyCheckout

4.93 out of 5 average rating, 196 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 spacesQuiet

4.99 out of 5 average rating, 116 reviews
Top Guest favourite
A spacious bedroom features sloped ceilings and soft green walls. A large bed is positioned against one wall, with a dark wood dresser and a gray ottoman nearby. A flat-screen television is mounted on the wall opposite the bed, illuminated by soft overhead lighting.
Apartment in Pittsburgh

Lavish Squirrel Hill - 3rd Floor

Nestled 2 blocks off of the Squirrel Hill business district this 3rd floor paradise has 3 bedrooms, full kitchen (walnut cabinets and granite counters), timeless black and white bathroom with cast iron tub. This oasis is "THE" place to stay while visiting Pittsburgh. Close to the Universities, and walking distance to 2 of Pittsburgh's parks (Frick and Schenley), you can literally catch a bus into town right outside the door (While still being an extremely quiet street with ample parking).

KitchenFamilyNearby

5.0 out of 5 average rating, 100 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.

FamilyIndoor spacesAccuracy

4.91 out of 5 average rating, 561 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).

FamilyKitchenDecor

4.93 out of 5 average rating, 180 reviews
Top Guest favourite
A wooden staircase leads to the upper level, framed by polished handrails and original woodwork. A woven runner rug adds texture to the hardwood floor. A small console table stands against the wall, paired with a green potted plant. Light filters in through a nearby doorway.
Home in Pittsburgh

Cheerful 3-bedroom home with on-street parking

Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

KitchenFamilyQuiet

5.0 out of 5 average rating, 115 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 spacesFamilyView

4.99 out of 5 average rating, 202 reviews
Top Guest favourite
A modern living area features a spacious sectional sofa in shades of gray, paired with a glass coffee table. Exposed brick adds warmth, while a sleek TV is mounted on the wall. A ceiling fan provides a comfortable atmosphere, and light wood flooring enhances the open space.
Home in Pittsburgh

6BR Group Retreat w/ BBQ, Game Room, and Parking

Enjoy comfort and modern style in this beautifully appointed 6-bedroom, 4-bath home in the East Liberty/Point Breeze area. Relax in the spacious living room, cook in the fully stocked kitchen, or unwind on the deck with the brand-new BBQ grill. With free parking for 4+ cars, a multi-game table, and two washers and dryers, this home is perfect for families, groups, and business travelers—just minutes from top dining, shopping, and entertainment.

KitchenIndoor spacesLaundry

4.99 out of 5 average rating, 104 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.

KitchenFamilyLaundry

4.95 out of 5 average rating, 175 reviews
Superhost
Home in Pittsburgh

Willy Wonka Themed | King Bed | Convenient parking

As Seen on CBS News, TribLive, & the Pittsburgh Post-Gazette – The Ultimate Willy Wonka Experience! You’ll explore the world of Wonka complete with oversized gummy bears, lollipops, and a wondrous boat in a completely unique, interactive and immersive Wonka experience just minutes away from Acrisure Stadium, PNC Park, & PPG Paints Arena. Explore vibrant cafes & art galleries in Lawrenceville, one of the coolest neighborhoods in Pittsburgh.

FamilyIndoor spacesAmenities

4.94 out of 5 average rating, 246 reviews

Popular amenities for Wilkinsburg family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

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 spacesKitchenHeating

4.88 out of 5 average rating, 129 reviews
Top 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

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 135 reviews
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

KitchenFamilyHot tub

4.92 out of 5 average rating, 209 reviews
Guest favourite
Home in North Side

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

KitchenFamilyOutdoor spaces

4.94 out of 5 average rating, 200 reviews
Guest favourite
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.
Home in Pittsburgh

Gorgeous Southside slopes house w/outdoor hot tub

FamilyKitchenWi-Fi

4.97 out of 5 average rating, 323 reviews
Guest favourite
An inviting outdoor seating area is presented, featuring a large sectional couch with decorative pillows, a coffee table, and a patterned rug. Lush greenery surrounds the space, providing privacy, while string lights overhead create a warm ambiance.
Home in Mount Washington

Hot Tub & Fire Pit Home Near Grandview Ave

Indoor spacesFamilyDecor

4.95 out of 5 average rating, 109 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

KitchenFamilyLayout

4.96 out of 5 average rating, 140 reviews
Guest favourite
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 North Side

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

Indoor spacesKitchenTV

4.94 out of 5 average rating, 139 reviews

Family- and pet-friendly home rentals

Top Guest favourite
An open kitchen area features modern black cabinetry paired with white countertops and stainless steel appliances. Ample natural light filters through large windows, illuminating the space. An adjacent staircase leads to the upper level, while the living area is visible in the background.
Apartment in Pittsburgh

Immaculate Double King Suite w/ Rooftop Terrace

FamilyIndoor spacesTV

4.99 out of 5 average rating, 142 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

KitchenFamilyView

4.84 out of 5 average rating, 132 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

KitchenFamilyCheckout

4.91 out of 5 average rating, 181 reviews
Guest favourite
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 spacesBackyard

4.84 out of 5 average rating, 127 reviews
Top Guest favourite
Townhouse in Mt. Lebanon

Private Mt Lebanon Retreat Near Airport/Downtown

FamilyKitchenBathroom

4.98 out of 5 average rating, 194 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

Indoor spacesKitchenGetting around

4.94 out of 5 average rating, 184 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

KitchenFamilyBackyard

4.87 out of 5 average rating, 85 reviews
Top Guest favourite
A warm living area features a stone fireplace gently glowing with light. Comfortable seating arrangements include a sofa and an inviting window nook with colorful cushions. Natural light enters through multiple windows, highlighting the wooden beam ceilings and rich tones of the walls.
Home in Pittsburgh

Cottage on a hill

Indoor spacesKitchenParking

4.95 out of 5 average rating, 78 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 spacesDecor

4.81 out of 5 average rating, 108 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 spacesKitchenLong stay

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

Charming Urban Pittsburgh Retreat!

Indoor spacesKitchenAmenities

4.78 out of 5 average rating, 114 reviews
Superhost
Home in Pittsburgh

A beautiful cozy home away from home!

Indoor spacesFamilyHospitality

4.67 out of 5 average rating, 18 reviews
Guest favourite
Home in South Side Flats

Rooftop Deck | Perfect for Entertaining | Upscale!

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 24 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

ViewCheck-inParking

4.91 out of 5 average rating, 23 reviews
Guest favourite
An inviting living area features a green sofa and a white couch, complemented by a wooden coffee table. Bar seating with stylish stools is situated near the kitchen area. Natural light enters through a large window, creating a bright and airy feel.
Home in West Mifflin

Cozy Home in Pgh area, Sleeps up to 10

KitchenFamilySleep quality

4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Pittsburgh

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

KitchenIndoor spacesComfort

4.88 out of 5 average rating, 59 reviews

When is the best time to visit Wilkinsburg?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$194 NZD$212 NZD$210 NZD$338 NZD$299 NZD$309 NZD$255 NZD$221 NZD$221 NZD$281 NZD$299 NZD$251 NZD
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