Family-friendly holiday rentals in Wilkinsburg

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.

4.99 out of 5 average rating, 129 reviews

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

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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.

4.81 out of 5 average rating, 255 reviews

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.

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4.99 out of 5 average rating, 111 reviews

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 spacesCheck-in

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.

5.0 out of 5 average rating, 100 reviews

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).

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Apartment in East Liberty

4.95 out of 5 average rating, 235 reviews

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!

KitchenIndoor spacesAccess

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.

4.91 out of 5 average rating, 561 reviews

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.

FamilyKitchenCheck-in

4.93 out of 5 average rating, 179 reviews

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).

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Apartment in Forest Hills

4.99 out of 5 average rating, 200 reviews

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.

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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.

4.99 out of 5 average rating, 101 reviews

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.

KitchenFamilyNearby

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.

4.95 out of 5 average rating, 174 reviews

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.

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4.94 out of 5 average rating, 245 reviews

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.

Indoor spacesFamilyCheckout

A shaded outdoor patio features a wooden gazebo with a table and six black metal chairs. Surrounding greenery includes various plants, with a vibrant mural on the adjacent wall providing a splash of color. Brick pathways define the patio space, enhancing the inviting ambiance.

4.89 out of 5 average rating, 101 reviews

Oasis by Frick Park w Garage Parking

Disappear into the oasis of this unique centrally located 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.

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Popular amenities for Wilkinsburg family-friendly rentals

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Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in Squirrel Hill North

4.9 out of 5 average rating, 146 reviews

Gather in Style | Walk to CMU | Sleeps 13

KitchenIndoor spacesCleanliness

4.88 out of 5 average rating, 128 reviews

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

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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.

4.95 out of 5 average rating, 134 reviews

Serene Secluded Hilltop Hideaway. Hot Tub Fire Pit

Indoor spacesFamilyComfort

4.96 out of 5 average rating, 138 reviews

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

KitchenFamilyCheckout

4.94 out of 5 average rating, 199 reviews

Home in North Side

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

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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, 322 reviews

Gorgeous Southside slopes house w/outdoor hot tub

Indoor spacesKitchenSleep quality

4.97 out of 5 average rating, 114 reviews

A single-story brick house is set against a colorful sunset sky. The inviting front porch features a classic wooden door flanked by large windows. Lush green grass leads up to the house, with a stone path and neatly trimmed hedges in the foreground.

Home in White Oak

Secluded Cozy 3 Bedroom Fun Bungalow

Indoor spacesKitchenAmenities

4.93 out of 5 average rating, 138 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 North Side

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

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Family- and pet-friendly home rentals

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.

4.84 out of 5 average rating, 131 reviews

City-Adjacent Wooded Retreat - Peace and Wildlife

FamilyIndoor spacesSleep quality

5.0 out of 5 average rating, 101 reviews

A cozy bedside view features a spacious bed with crisp white linens and a decorative pillow. A wooden nightstand holds a phone, while a stylish lamp provides soft lighting. Behind, textured dark paneling creates a modern backdrop, complemented by an abstract wall art piece.

Apartment in Shadyside

Immaculate Double King Suite| 2 Decks| A+ Location

KitchenFamilyView

4.98 out of 5 average rating, 113 reviews

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

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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.

4.84 out of 5 average rating, 127 reviews

Pet Friendly Pittsburgh Home Near Zoo, Sleeps 12

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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, 921 reviews

Spacious, warm, private apartment near CMU /Pitt

KitchenFamilyQuiet

4.91 out of 5 average rating, 180 reviews

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

KitchenIndoor spacesCleanliness

4.99 out of 5 average rating, 191 reviews

Townhouse in Mt. Lebanon

Private Mt Lebanon Retreat Near Airport/Downtown

FamilyKitchenParking

4.86 out of 5 average rating, 285 reviews

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!

KitchenIndoor spacesAmenities

Family-friendly home rentals with a pool

4.81 out of 5 average rating, 107 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 Dormont

Renovated Cozy Duplex w/pool, Close to downtown

KitchenIndoor spacesComfort

4.87 out of 5 average rating, 197 reviews

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

KitchenFamilyParking

4.78 out of 5 average rating, 113 reviews

Home in Highland Park

Charming Urban Pittsburgh Retreat!

KitchenFamilyParking

4.67 out of 5 average rating, 18 reviews

A beautiful cozy home away from home!

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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.

4.91 out of 5 average rating, 23 reviews

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

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5.0 out of 5 average rating, 23 reviews

Home in South Side Flats

Rooftop Deck | Perfect for Entertaining | Upscale!

Indoor spacesFamilyCheck-in

4.88 out of 5 average rating, 26 reviews

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

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