Pet-friendly holiday 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.

4.98 out of 5 average rating, 52 reviews

Steep Retreat Hazelwood Greenway

Take it easy at this unique retreat where the city and greenway meet. This 2 BD/ 1.5 BA home, built during the depression and renovated during the pandemic, boasts of these eras. It is located in the mid heights of Hazelwood just below the cemetery on a dead end street. It requires a 42 step ascent to the entrance. It has more decks than bedrooms and a hot tub that shares the lower deck with a propane grill. Nearby: Waterfront, Southside, Squirrel Hill, the City Parks and the GAP trail.

4.99 out of 5 average rating, 99 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!

An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.

4.95 out of 5 average rating, 184 reviews

Cozy 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, 3 min drive to CMU & Pitt! 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!

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.

4.98 out of 5 average rating, 110 reviews

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!

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.

4.89 out of 5 average rating, 35 reviews

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!

4.99 out of 5 average rating, 178 reviews

Townhouse in Pittsburgh

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!

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, 46 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!

The kitchen features modern appliances set against a striking brick accent wall. Light-colored cabinetry complements the sleek countertops, while large windows allow natural light to illuminate the space. Ample storage is provided by the cabinets and drawers, creating a functional cooking area.

4.96 out of 5 average rating, 85 reviews

Stylish 3BR w/ Free Parking Near Shopping & Dining

Enjoy a refined stay in this beautifully updated 3-bedroom, 2-bath apartment in the heart of Point Breeze. The home features three king beds, a spacious living area, a fully equipped kitchen, and a private deck—perfect for relaxing after a day in the city. Guests can enjoy Netflix, in-unit laundry, and complimentary parking for two vehicles. Ideally located just steps from premier shopping, dining, and entertainment, this home is well-suited for both business and leisure travelers.

Superhost

A vibrant mural of Pittsburgh's skyline brings energy to a modern space. A spacious bed with soft linens is positioned beside a window, allowing natural light. The image also showcases a fenced backyard with a hot tub and outdoor seating, ideal for relaxation.

4.88 out of 5 average rating, 41 reviews

NEW Gorgeous 4bd near universities Hot tub + Games

Wow! Enjoy an upscale home located in the heart of Pittsburgh! A wonderful combination of professional design and modern amenities makes this the perfect place to stay while visiting the Burgh. From Pittsburgh-inspired decorations to thoughtfully designed interiors, Air hockey + Ping pong table to the relaxing fenced backyard with a hot tub, this house is the place to be in the city! 0.9 Miles to Univ. of Pittsburgh 1.4 Miles to Carnegie Mellon Univ. 9 Min Drive to Downtown

5 out of 5 average rating, 14 reviews

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

✨ Welcome to our large, stylish studio in the heart of Shadyside! This modern, fully furnished suite features sleek décor, a fully equipped kitchen, a cozy living space, and a luxurious king bed. Enjoy top-tier amenities, including: 🔹 Fitness Center & Yoga Studio 🔹 Free Street Parking 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Retail 🔹 Bike Storage Room

The living area features a comfortable couch and a coffee table, with a wall of windows allowing natural light to fill the space. A desk and chair are positioned for workspace, while decorative elements and plants add a homely touch.