Pet-friendly holiday rentals in Squirrel Hill

Cozy! Micro Loft apartment! in N Oakland, sleeps 1

Come and relax in our new location! Perfect for work and pleasure! 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 that flood the space with natural light. These units come fully furnished and micro kitchen (microwave and mini fridge) and all your required accessories for you to just drop your suitcase and start r

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.

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!

River Ridge Retreat

Discover the charm of our Braddock, PA Airbnb! Just minutes from all Pittsburgh attractions, reach any city hotspot within 20 minutes. Close to Regent Square, Bakery Square, and Point Breeze. Explore Kennywood Park across the river and enjoy quick access to Sandcastle Waterpark. Whether it’s UPMC, downtown, CMU, or The Strip, we’re minutes away from it all! Your perfect Pittsburgh getaway awaits! *If you enjoy this space, the owners are amenable to selling. Please contact for more information

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!

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!

New Lux King Suite | Free Parking+Gym | Near UPMC

✨ Welcome to our stylish and modern apartment in the heart of Shadyside! This fully furnished 1 bedroom suite features sleek décor, a fully equipped kitchen, cozy living space and 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

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!

Friendship Retreat~B | 1BR w/ Gourmet Kitchen

Enjoy a stylish first-floor 1BR with a gourmet kitchen featuring high-end appliances and a spacious living area perfect for relaxing or entertaining. The queen-size bedroom offers a comfortable night’s sleep. High-speed WiFi and a dedicated workspace make it ideal for business travelers or remote work. Access to shared parking (6 spots, first-come, first-served). Located near West Penn Hospital and UPMC Shadyside, perfect for couples, visiting families, or medical stays.

Cozy and Spacious Guest Suite in Greenfield

This newly renovated suite is the downstairs unit of a three story house (the upper two floors are a completely separate living area). This space has plenty of free street parking located just outside of its own entrance. Carnegie Mellon University and the University of Pittsburgh are both about a 5-7 minute drive away, and to get downtown it is typically a 10 minute drive. There is a bus stop at the end of the street that can take you just about anywhere in Pittsburgh.

"The Spa Room" Renovated Flashlight Factory

Beautiful 1700 sq ft loft apartment. Located in historic north side. Minutes from both the stadiums, night life, casino, and museums! Best suited for 2 but can accommodate 4. Hard wood floors. Exposed brick. Huge state of the art kitchen. Beautifully executed bathroom with a walk in shower and massive soaking tub. If the bathtub isn't enough for you there is a hot tub located in the light well 1 floor down from the loft. Our other AirB&B is a Plus.

"April's Haven" Regent Square King Frick Park

Take a break and unwind at this peaceful retreat. Two bedroom third floor apartment walking distance to Frick Park, shops, restaurants, and bars on Braddock. Quiet historic neighborhood with brick streets. Hike or mountain bike on the 22 miles of trails in fabulous Frick Park. Short drive or easy bus ride to universities and UPMC facilities. Don't need 2 bedrooms? Traveling with others? Check out my other 1bd listing. https://air.tl/JAWjri9Y