Pet-friendly vacation rentals in Squirrel Hill

4.91 out of 5 average rating, 86 reviews

Prime 5-Bed: Hot Tub, PITT, CMU, Schenley Park

Welcome to my home away from home! This spacious 5-bedroom, 3-bath retreat blends comfort and convenience. Relax in the hot tub after exploring nearbySchenley Park and Phipps Conservatory. Ideal for events at the University of Pittsburgh or CMU, it's just steps from both campuses. Also perfect for Steelers or Penguins fans, with the stadiums 5-10 minutes away. Enjoy modern amenities, a fully equipped kitchen, and a cozy living space, perfect for families, academics, and sports enthusiasts alike.

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!

4.98 out of 5 average rating, 114 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!

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

Welcome to our cozy, Gothic Boho retreat in the heart of Squirrel Hill! This spacious & stylish home is perfect for families, friend groups, or university visits- just minutes from CMU, Pitt and Chatham- along with several cafe's & shops within walking distance. ⭐4 bedrooms (2 Queen, 2 Full, 1 Twin daybed, 2 Twin rollaways) ⭐Free Off-street parking (2 cars) ⭐Free Washer / dryer ⭐Walkable ⭐Bus stop just 200 ft away Our team is here for you 24/7 before, during and after your stay with us!

4.89 out of 5 average rating, 44 reviews

4.95 out of 5 average rating, 142 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!

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.

Superhost

A three-story brick house is displayed, featuring a wide staircase leading to a front porch. Large windows allow natural light to enter, and colorful flower beds with red blooms enhance the entrance. Lush green foliage surrounds the property, creating a welcoming exterior.

4.89 out of 5 average rating, 47 reviews

Cheerful 4 Bedroom Home in Squirrel Hill!

Coming to Pittsburgh but need more space and privacy than a hotel? Well, ditch the hotel or your in law's home and book this amazing home in the Squirrel Hill South Neighborhood. With great access to downtown Pittsburgh, PNC Park and Heinz Field you'll love this for sporting events. Just a short 3 mile drive to Carnegie Mellon and the University of Pittsburgh; so, whether you are coming in for a weekend to see you college student or graduation, the Steel City Getaway has you covered!

4.88 out of 5 average rating, 248 reviews

The living room features a spacious gray sectional sofa positioned near large windows that allow natural light to fill the space. A modern glass coffee table is centered on a soft area rug, while white interior doors provide access to closet space.

Apartment in Shadyside

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

Superhost

The living area features high ceilings with natural light streaming through large windows. A modern sofa is paired with two round coffee tables placed on a patterned area rug. Vibrant wall art adds character to the space, enhancing the industrial aesthetic.

Loft in Pittsburgh

Industrial Loft 5 min to Children’s Hospital, slps

Come and relax in our new location! This historic warehouse was converted into apartments but still holds its original architectural features! Enjoy the industrial modern aesthetic with 15-foot-high ceilings, brick walls, original concrete floors, and atrium skylights with natural light. These units come fully furnished and most have full kitchens and all your required accessories for you to just drop your suitcase and start relaxing. **NOW PET FRIENDLY-$50.00 PET FEE PER STAY**

4.85 out of 5 average rating, 170 reviews

Superhost

Apartment in Shadyside

StudioApt w/Gym+eV+Free Parking+Near Pitt Uni UPMC

╰✮⋆ Welcome to our stunning cozy 1-bed studio in the heart of Shadyside! Whether you're visiting for work or taking some time to explore Pittsburgh, this comfortable space offers a simple blend of style, convenience, and comfort . Nestled in a prime location, our unit provides easy access to the city’s top attractions, making it the ideal base for exploring everything Pittsburgh has to offer *ID and Background verification needed * ───────୨ৎ───────

4.91 out of 5 average rating, 87 reviews

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, 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.