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

WalkabilityPetsLocation

4.88 out of 5 average rating, 308 reviews

4.95 out of 5 average rating, 179 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

Outdoor spacesPetsWi-Fi

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.

PetsOutdoor spacesParks

4.84 out of 5 average rating, 131 reviews

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.

Outdoor spacesPetsBackyard

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!

Outdoor spacesPetsLaundry

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!

PetsOutdoor spacesIndoor spaces

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!

PetsWalkabilityCleanliness

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.

WalkabilityOutdoor spacesLocation

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.

Outdoor spacesWalkabilityDecor

4.99 out of 5 average rating, 148 reviews

A spacious living area features a comfortable sectional sofa and a pair of armchairs, accented by soft seating cushions. Large windows are adorned with sheer curtains, allowing natural light to brighten the room. A decorative area rug lies on the hardwood floor, and small tables complete the arrangement.

Home in Mt. Lebanon

Seneca Place: A historic home in Mount Lebanon.

Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

Outdoor spacesPetsTV

4.93 out of 5 average rating, 280 reviews

The living area features a cozy couch with a decorative throw, providing a warm contrast to the exposed brick wall. A dining area with two stools is situated near the kitchen, while a large smart TV displays various streaming options.

Apartment in Shadyside

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

WalkabilityPetsBiking

4.97 out of 5 average rating, 67 reviews

Family & Friendly Stay in Pittsburgh, PA.

This cozy home is the perfect balance of comfort and convenience. Located in Eastmont, a quiet neighborhood. You're just minutes from all the shops, restaurants, and essentials in Pittsburgh and Monroeville, making it ideal for families, couples, or professionals needing a functional, well-located stay. Inside, you’ll find a warm, thoughtfully designed space with modern amenities, rustic touches, and everything needed to feel at home.

PetsOutdoor spacesBathroom

Popular amenities for Wilkinsburg pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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

PetsOutdoor spacesCleanliness

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

WalkabilityPetsSleep quality

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

PetsOutdoor spacesCheckout

4.99 out of 5 average rating, 232 reviews

Home in South Side Flats

Historic South Side Home • Former Convent

WalkabilityOutdoor spacesFamily

4.9 out of 5 average rating, 237 reviews

A spacious living room features a large sectional sofa oriented towards a wall-mounted projector screen. Stone accents on the fireplace create a focal point, while recessed lighting adds brightness. Dark blue walls are complemented by artwork and decorative elements.

Home in North Side

Huge 6 BDRM min to Downtown & Stadiums w/ parking

PetsWalkabilityValue

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

PetsOutdoor spacesHospitality

4.92 out of 5 average rating, 404 reviews

A cozy living room features deep blue walls with natural light coming through the window. Two gray sofas are arranged around a low coffee table atop a patterned area rug. A brick fireplace serves as a focal point, adorned with decorative items and artwork.

Home in North Side

★2 Car off-street parking★ Outdoor dining ♥view♥

Outdoor spacesPetsBathroom

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

PetsOutdoor spacesKitchen

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

WalkabilityOutdoor spacesLaundry

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

Outdoor spacesPetsBackyard

4.92 out of 5 average rating, 13 reviews

Apartment in North Side

FIDO PLUS TWO 1.5 miles to Acrisure Stadium

Outdoor spacesPetsPool

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

Outdoor spacesPetsNearby

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

WalkabilityPetsFamily

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

Outdoor spacesCleanlinessKitchen

4.91 out of 5 average rating, 23 reviews

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

Outdoor spacesWalkabilityBathroom

5.0 out of 5 average rating, 12 reviews

Home in Forest Hills

Posh Pittsburgh: two stories with terrace & pool

PetsOutdoor spacesComfort

Private, pet-friendly home rentals

5.0 out of 5 average rating, 19 reviews

Apartment in Shadyside

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

WalkabilityCheckoutComfort

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, 99 reviews

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

Outdoor spacesWalkabilityNearby

Apartment in East Liberty

Marble Bath Penthouse: King Bed, Laundry, Parking

WalkabilityValueComfort

4.97 out of 5 average rating, 36 reviews

4.85 out of 5 average rating, 46 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.

Apartment in Pittsburgh

Hydee's Hideaway

AccessFamilyComfort

5.0 out of 5 average rating, 24 reviews

Home in Bloomfield

Upscale 3BR | Prime Location + Off-Street Parking!

PetsWalkabilityLocation

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

WalkabilityOutdoor spacesKitchen

4.93 out of 5 average rating, 14 reviews

Apartment in Bloomfield

Wine cellar 2BR | Free Parking / near CMU & PITT

FamilyQuietHospitality