Holiday houses 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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Apartment in Downtown Pittsburgh

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

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4.9 out of 5 average rating, 383 reviews

Superhost

4.81 out of 5 average rating, 298 reviews

Private Suite Pittsburgh's East End

Enjoy an entire 1st and second floor in historic Hamnett Place! Located in a 19th century duplex, it includes a full private bathroom, two bedrooms and private entrance with kitchen access. Perfect for two or three, it can accommodate up to four. This is a private stay and not a shared home. Free parking and blocks from transportation hub, 15 minutes to downtown, it is located in a sleepy historic suburb of Pittsburgh. For groups of 5 or more, please check out airbnb.com/h/eastendinn

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4.99 out of 5 average rating, 116 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!

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4.95 out of 5 average rating, 141 reviews

A living area features large windows allowing ample natural light, with a gray sofa and two chairs arranged around a dark coffee table. The modern kitchen with stainless steel appliances is visible in the background, complemented by stylish cabinetry and a dining area.

Apartment in Shadyside

Huge King Suite Just off Walnut

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, CMU & Pitt! HUGE 2 Floor 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!

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4.94 out of 5 average rating, 51 reviews

Walk to Cafes + Frick Park From A Breezy Retreat

Welcome to the quiet, friendly, desirable Regent Square, and and an ideal home for Frick Park visitors, walkers, and bikers alike. Designed both for cozying up inside and enjoying fresh air! Featuring 4 outdoor spaces: * Relax on a shaded front balcony * Soak up rays on the upper deck * Dine al fresco on the kitchen deck * Swing away the day on the front porch A quick, pleasant stroll away from beloved local cafes, plus close proximity to Squirrel Hill and Shadyside dining and shopping.

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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.

4.87 out of 5 average rating, 85 reviews

The Stone House

Bring the whole family to this retreat with lots of room for fun. 13 minutes to downtown, stadiums, universities and hospitals! Situated next to a 400 acre park on a private road, this midcentury modern house has been completely updated- with special attention to maintaining the relaxing yet classy feel of the 1950's. The house sits on the owners historic 12-acre farm in one of Pittsburgh's verdant suburban communities, close to main arteries- yet holding a rural, relaxed atmosphere.

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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.

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4.93 out of 5 average rating, 180 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

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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4.99 out of 5 average rating, 200 reviews

A modern kitchen is showcased, featuring stainless steel appliances and a spacious island with seating for two. Warm wood cabinetry complements the light-colored countertops. The open layout connects to a dining area, enriched by natural light from the window and exposed brick accents on the walls.

4.99 out of 5 average rating, 104 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.

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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, 175 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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Popular amenities for Wilkinsburg holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Wilkinsburg

4.97 out of 5 average rating, 38 reviews

East End Pittsburgh 4 Bedroom Getaway

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4.99 out of 5 average rating, 97 reviews

Modern 2BR • Family-Friendly • Walk to Frick Park

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A comfortable living area features plush gray seating, complemented by a cozy area rug. A small, black side table is positioned beside the seating, and a modern electric fireplace provides a warm ambiance against a textured wall. A potted plant adds a touch of greenery.

4.89 out of 5 average rating, 66 reviews

The Quiet Cozy Getaway! Located on a private road!

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5.0 out of 5 average rating, 8 reviews

Home in Forest Hills

The Westinghouse -Close To Pittsburgh's Best!

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4.79 out of 5 average rating, 38 reviews

Home in Forest Hills

Cozy Spacious home in suburban Pittsburgh

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The loft features vaulted tin ceilings, showcasing natural light filtering through the windows. A comfortable beige sofa sits in the center, complemented by a wooden table and chairs in the background. Exposed brick walls add to the unique charm.

4.79 out of 5 average rating, 269 reviews

private attic loft, and pet friendly

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A dining table with light-colored chairs is set beneath a chandelier, surrounded by colorful walls and lush indoor plants. A vibrant area rug adds warmth to the space, while a welcoming living area with large windows is visible in the background, providing a glimpse of the outdoor scenery.

4.67 out of 5 average rating, 12 reviews

Easy Access to Pittsburgh: Urban Retreat w/ Deck

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