Pet-friendly holiday rentals in Wilkinsburg

Townhouse in South Side Flats

The modern kitchen features white cabinetry, stainless steel appliances, and a spacious central island with yellow bar stools. Sleek countertops and stylish pendant lighting enhance the functional space, which is complemented by warm wooden flooring.

Amazingly Homey w/Garage + Outdoor Space! 5B/2B

Magnificent 5bedroom Southside townhome with private garage parking! Originally built in the early 1900s, the property recently underwent a full renovation which preserved it's character & charm, but added wonderful modern amenities. Located in one of the best locations in Pittsburgh, just a short walk to the Southside Strip. The property has a lovely outdoor patio with furniture and grill. It's a wonderful property for traveling business partners who want space, families, and small groups alike

4.88 out of 5 average rating, 308 reviews

4.95 out of 5 average rating, 180 reviews

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

Experience unparalleled luxury in this spacious 5-bedroom, 3.5-bathroom haven, perfectly situated in the heart of Pittsburgh. Boasting not one, but two roof decks, you'll have the finest city vistas right at your fingertips. Relax by the indoor-outdoor gas fireplace this is a serene escape amidst the urban hustle. With the addition of garage parking for 1 vehicle + Parking pad directly in front of the garage door, your downtown retreat combines modern elegance with supreme comfort, promising a m

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.

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

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.

4.99 out of 5 average rating, 109 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!

4.97 out of 5 average rating, 184 reviews

A comfortable living room features a spacious sectional sofa adorned with a textured throw blanket. A large smart TV sits on a media console, displaying streaming options. Natural light enters through a window, complemented by modern furnishings, including two accent chairs and decorative plants.

Apartment in Shadyside

Upscale Double King Suite~Steps to Walnut~Parking!

2 OFF STREET PARKING SPACES INCLUDED FOR FREE! In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 2BR (+sofa bed)/1bath apartment w/ private balcony in a prime location, restaurants, shops, coffee shops, & fitness studios close by. The building was gutted and remodeled, everything down to the studs is brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays! Reach out to book your stay today!

Apartment in East Liberty

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.

Upscale King Bed Suite |ADA w/ Free parking!

Enjoy our spacious king-sized bed suite located in the safe, central Friendship neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Whole Foods and short walk to Yinz Coffee shop! ⭐King bed (Memory foam mattress) ⭐Queen pull out bed ⭐Pack n play ⭐ADA Accessible! ⭐In-unit washer/ dryer ⭐Large desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt! ⭐$0 cleaning fee!

4.97 out of 5 average rating, 229 reviews

4.91 out of 5 average rating, 179 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

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost you see per night is for 2 guests. Added adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day. I will collect that later.

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

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!

4.99 out of 5 average rating, 187 reviews

Townhouse in Mt. Lebanon

Private Mt Lebanon Retreat Near Airport/Downtown

Welcome to your home away from home! This recently remodeled townhouse offers the perfect blend of comfort and style, situated just 20 minutes from the air port and city’s major stadiums. Ideal for all travelers, our home is nestled in a peaceful suburb with easy access to public transportation, nearby parks, and charming small businesses and shops. • Two bedrooms featuring king-sized beds. • An expansive kitchen, complete with peninsula and breakfast bar. We look forward to hosting you!

4.94 out of 5 average rating, 49 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.

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, 84 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.

Popular amenities for Wilkinsburg pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.83 out of 5 average rating, 160 reviews

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

4.97 out of 5 average rating, 194 reviews

A modern kitchen features a large, central island with seating for several guests. Equipped with stainless steel appliances, it showcases sleek cabinetry and a mosaic backsplash. Natural light filters through multiple windows, creating a bright and welcoming atmosphere for meal preparation and gatherings.

Home in Mount Washington

Scenic Haven: Downtown 3BR/2BA w/Parking + Patio

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

4.99 out of 5 average rating, 100 reviews

The game room features a combination table for dining, ping pong, and pool. An electric fireplace and a golden tee arcade game add warmth and entertainment. Natural light enters through large windows adorned with curtains, while a vibrant mural decorates one wall, enhancing the lively atmosphere.

Home in North Side

Spacious 4BR | 2 Kings, Firepit, Arcade + Parking

4.99 out of 5 average rating, 232 reviews

Home in South Side Flats

Historic South Side Home • Former Convent

4.91 out of 5 average rating, 447 reviews

A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.

Home in South Side Flats

Urban converted gas station in heart of South Side

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.

4.94 out of 5 average rating, 444 reviews

Large house to relax with friends and family

A comfortable living area features a gray sectional sofa and a glass coffee table on a natural fiber rug. Framed artwork lines the wall, while a small dining area with a chair and table is visible in the background. Natural light filters through the window.

4.81 out of 5 average rating, 125 reviews

The Nest in the North Hills.

Pet-friendly home rentals with a pool

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

4.92 out of 5 average rating, 25 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

4.92 out of 5 average rating, 13 reviews

Apartment in North Side

FIDO PLUS TWO 1.5 miles to Acrisure Stadium

4.57 out of 5 average rating, 63 reviews

A private pool is set within a spacious wooden deck, surrounded by lounge chairs and shaded areas. A vibrant beach ball floats on the water, and an umbrella offers shade nearby. Lush greenery is visible in the background, enhancing the outdoor space.

Home in New Kensington

Seasonal Pool Retreat | Fire Pit & Large Deck

4.95 out of 5 average rating, 83 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

4.79 out of 5 average rating, 19 reviews

A refreshing swimming pool is framed by a spacious patio lined with lounge chairs and umbrellas. Lush greenery surrounds the area, providing a relaxing atmosphere. A stone fireplace is visible in the background, contributing to the overall outdoor retreat feel.

Home in Carnegie

The Burgh Beach House

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

5.0 out of 5 average rating, 12 reviews

Home in Forest Hills

Posh Pittsburgh: two stories with terrace & pool

Private, pet-friendly home rentals

Home in Squirrel Hill North

The living room showcases a warm Gothic Boho design, featuring a plush sofa and two comfortable chairs. A central round coffee table sits atop a textured rug, while natural light filters through sheer curtains. An ornate chandelier hangs above, adding elegance to the space.

Gothic Boho Hideaway |4BR |Parking |Safe &walkable

4.88 out of 5 average rating, 41 reviews

The exterior of the two-story brick house is presented with a sloped roof and a prominent chimney. A neatly trimmed lawn includes a small garden area bordering a stone pathway leading to the front door, where a welcoming porch is visible.

4.96 out of 5 average rating, 28 reviews

JOY-HOUSE :Single family Tudor

A spacious living area is highlighted by a large sectional sofa adorned with a striped blanket and vibrant orange pillow. A stylish round coffee table is centered on a striped area rug. Natural light streams through multiple windows, enhancing the brick accent wall and modern decor.

4.98 out of 5 average rating, 91 reviews

Stylish 3BR w/ Free Parking Near Dining & Shopping

5.0 out of 5 average rating, 19 reviews

Apartment in Shadyside

King Bed | Free Parking | Gym | UPMC, Pitt & CMU

Apartment in East Liberty

Marble Bath Penthouse: King Bed, Laundry, Parking

4.97 out of 5 average rating, 36 reviews

A living area includes a dark brown sectional sofa and a matching reclining chair, both featuring quilted detailing. A glass coffee table sits atop a patterned area rug, which incorporates shades of gray and yellow. Natural light is evident, enhancing the space's openness.

4.85 out of 5 average rating, 46 reviews

Hydee's Hideaway

A rooftop deck features comfortable light blue seating and a fire pit, with stunning views of a historic church's twin towers in the background. The vibrant sky is adorned with fluffy clouds, creating a serene atmosphere for relaxation.

5.0 out of 5 average rating, 72 reviews

Skyline Roof Deck | Boutique Stay | Pet Friendly