Apartment holiday rentals in Squirrel Hill

The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.

4.97 out of 5 average rating, 146 reviews

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

A bright living area is showcased with a comfortable sofa adorned with pillows and a soft throw blanket. A round coffee table sits in front, and a subtle rug grounds the space. A modern lamp and decorative plant add warmth, while a kitchen can be glimpsed in the background.

4.92 out of 5 average rating, 120 reviews

King Bed On Butler Street, Middle of Everything!

If you're the type of traveler that wants to be steps from the fun, this is your place! Our second floor apartment features a well stocked kitchen, quality amenities, smart 4K TVs (including bedroom), a king bed, 2 desks (in 2 separate rooms, perfect for a work from home couple) and more! Three breweries and 20+ bars & restaurants are within 3 blocks of your place. It's perfect for when you want a night out - but with our cozy place you'll be tempted to stay in & relax while watching Netflix!

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.

4.97 out of 5 average rating, 139 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!

The open living area features a modern kitchen with white cabinetry and stainless steel appliances. A wooden dining table with bar stools is positioned next to the kitchen, while a cozy sofa is adorned with decorative pillows. Exposed brick walls add character to the space.

4.99 out of 5 average rating, 147 reviews

Luxury King Suite Near Shadyside Hospital

The Pitt Shuttle is just a block away, and the apartment is 0.8 miles from Pitt and CMU campuses. This newly remodeled 2BR/1BA first-floor apartment is fully stocked and pristine, perfect for a Steeler game, family getaway, or hospital visit. Close to UPMC Shadyside, UPMC Presby, West Penn, and the VA, with restaurants, bars, and shops within walking distance. Whether you're visiting for work or play, this stylish apartment offers the comfort and convenience you need to feel at home.

An inviting living space features a comfortable sectional sofa and a television mounted on the wall. Light streams in through large windows adorned with shutters, highlighting a potted plant and decorative wall hanging. A small dining table with a patterned tablecloth is visible nearby.

4.98 out of 5 average rating, 132 reviews

"April's Retreat" Regent Square King Bed Frick Prk

Take it easy at this tranquil getaway that is close to everything Pittsburgh. You'll enjoy the one bedroom apartment on the 2nd floor of this historic building in Regent Square. Walk to Frick Park, restaurants, coffee shops and bars on Braddock. Hike or mountain bike on the 22 miles of trails. Small and well-appointed kitchen if you like to prepare your own meals. Tons of natural light. Close to bus routes. Need more space? Traveling with others? Check out my other 2bd listing.

Superhost

A modern living area features a sectional gray sofa positioned beside a light wood coffee table. A flat-screen TV is mounted on the wall, and a decorative plant adds greenery. Large windows with blinds provide natural light, illuminating the light wood flooring.

4.91 out of 5 average rating, 130 reviews

Shadyside/Pittsburgh, Modern & Quiet 1BD w/Prkng

Modern, quiet and family oriented 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 Bedroom & Dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

A modern living area features a light grey sectional sofa draped with a vibrant orange throw. Colorful artwork adorns the wall above a sleek television, while a spiral staircase provides access to the upper levels. A dining area with pink chairs is visible in the background.

4.99 out of 5 average rating, 158 reviews

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

Superhost

The loft features vaulted tin ceilings, showcasing natural light filtering through the windows. A comfortable beige sofa sits in the center, complemented by a wooden table and chairs in the background. Exposed brick walls add to the unique charm.

4.8 out of 5 average rating, 250 reviews

private attic loft, and pet friendly

unique one of a kind place. Its a one bedroom attic loft , that has been painstakingly renovated and built with creative little details everywhere. sometimes it's almost like you're in a tree house. It has 20'-vaulted tin ceilings and antique appliances and fixtures. Everything has been updated and works perfectly. There's a Nespresso machine and nice cotton linens on a memory foam king-size bed. It's a great romantic retreat or place to set up shop and stay awhile.

A bright kitchen space is shown, featuring modern cabinetry and stainless steel appliances. A central island with seating for four is highlighted, complemented by a stylish pendant light above. Natural light streams in through a nearby window, enhancing the clean, inviting atmosphere.

4.96 out of 5 average rating, 346 reviews

Cozy Entire APT B Friendship Park & Free Parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

A modern kitchen area features sleek cabinetry alongside a wooden countertop and stainless-steel appliances. A spacious gray sofa with decorative pillows is situated nearby, providing a comfortable seating option. Light streams through a window, illuminating the tiled floor and brick accent wall.

4.9 out of 5 average rating, 471 reviews

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

This Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, a new sleeper sofa, a full kitchen and a full bathroom with a private entrance on the 2rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

The living room features a spacious grey sofa adorned with a navy throw blanket. A blue and cream patterned rug covers the hardwood floor, while natural light streams through sheer white curtains. A light fixture and a small side table complete the serene ambiance.

4.95 out of 5 average rating, 146 reviews

Newly remodeled 2 bedroom apartment

Newly remodeled 2 bedroom apartment on the first floor of a duplex located in a quiet neighborhood. Fully equipped kitchen. Roku Tv with cable and free wifi. Plenty of on street parking. Walking distance to Frick Park and great neighborhood bars/ restaurants. Under one mile to Regent Square bars and restaurants. Just a few minute car ride to the heart of Squirrel Hill. Under ten minute car ride to downtown Pittsburgh. Self check-in.

Superhost

The bedroom features a spacious king bed with a memory foam mattress, accompanied by a plush blanket. A large window allows natural light to fill the room, complemented by stylish curtains. An office desk with a chair and a lamp are present, along with a closet and bedside table.