Holiday rentals in Squirrel Hill

A cozy living room area showcases a brown leather sofa adorned with decorative pillows. Two lamps illuminate the space, and a round coffee table is positioned in front of the sofa. Artwork is displayed on the walls, contributing to the classic decor.

4.99 out of 5 average rating, 120 reviews

2BR Apt. /Pittsburgh/East/Regent Square/Frick Park

First floor 2-bedroom apartment with classic decor. Modern bath/kitchen with complete utensils. Wi-Fi & wired gigabit network. Two TVs with service. Appropriate for business traveler, families with older children. Living and dining room accommodates 8-10 people. Convenient to downtown, Oakland/universities. Across street parking. Nearby restaurant/stores and park in walking distance. Open bar. No per-person or amenities charges. Virtual tour at https://my.matterport.com/show/?m=BFeAkSV4ekM

Superhost

The dining area features a wooden table surrounded by six chairs, complemented by a woven area rug. Modern pendant lighting hangs above, illuminating the space. The open layout connects to a fully equipped kitchen with stainless appliances and an island with seating.

Home in Pittsburgh

4.78 out of 5 average rating, 266 reviews

Sq. Hill 🏡 Frick Park 🚵‍♀️ Parking 👑 King Bed

Newly remodeled 4BR/2.5BA home on a quiet Squirrel Hill street—steps to Frick Park & Blue Slide Park. Sleeps 8 (king + memory-foam beds). Cook in the fully stocked kitchen w/stainless appliances, coffee & tea bar, dine at the table for 6 + breakfast bar, then unwind with fast Wi-Fi, dedicated workspace, Roku TV, DirecTV Stream, and in-home washer/dryer. Easy keypad self check-in , driveway and easy street parking. Walk to Murray Ave shops, cafes & 2 Starbucks. Minutes to CMU, Pitt & downtown.

A mid-sized living room features a gray futon and several chairs arranged around a light-colored coffee table. An area rug with a floral pattern covers the floor, and a cozy ambiance is provided by overhead lights and lamps. Exposed wooden panels bring warmth to the space.

4.83 out of 5 average rating, 138 reviews

Darling basement one-bedroom

This simple basement suite is safe and convenient. Located on a quiet street with walking to restaurants, library, and movie theater with easy bus access to Pitt, CMU. Equidistant to Frick and Schenley Parks with hiking and biking trails, tennis, soccer, playground. Private entrance, off steep-ish driveway . Free street parking. Lower ceiling. No pets, smoking outside only. I have my children every other weekend; they have quiet hours 9pm-8am. Please inquire for dates if that might annoy.

A modern living room features a comfortable sofa with decorative pillows, complemented by an armchair and a coffee table. The kitchen area showcases a marble countertop, with bar stools provided for dining. Bright wall art enhances the space, illuminated by natural light from the window.

4.91 out of 5 average rating, 294 reviews

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet

Stylish and freshly renovated 1 BR/ 1 bath apartment perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! Fully equipped for an extended stay, weekend getaway, or just a place to crash for the night. ⭐️Super comfy queen memory foam mattress 🌟24/7 Guest support ⭐️Free off-street parking! 🌟Fully stocked & equipped kitchen ⭐️Queen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ⭐️Laundry (Free and in-unit)

4.93 out of 5 average rating, 352 reviews

The kitchen area features dark wood cabinetry with a granite countertop. Stainless steel appliances, including a microwave and refrigerator, are neatly installed. A tiled backsplash in a soft grey hue complements the modern design. A small dining table with two chairs occupies the space.

Home in Pittsburgh

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

A spacious sleeping area is highlighted by a wooden bed with neutral bedding. A cozy fireplace is located beneath a clock, accompanied by a decorative plant and a circular seating area. Natural light enters through the windows, enhancing the room’s bright atmosphere.

4.92 out of 5 average rating, 160 reviews

Shadyside/Central @4 Stylish&Central Studio w/Prkg

Stylish and Central family oriented modern Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen 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.

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.

4.93 out of 5 average rating, 248 reviews

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!

5 out of 5 average rating, 99 reviews

A wooden staircase leads to the upper level, framed by polished handrails and original woodwork. A woven runner rug adds texture to the hardwood floor. A small console table stands against the wall, paired with a green potted plant. Light filters in through a nearby doorway.

Home in Pittsburgh

Cheerful 3-bedroom home with on-street parking

Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

A cozy living area is adorned with a plush sectional sofa in neutral tones. A modern stone fireplace serves as a focal point, complemented by a large wall-mounted television. Natural light filters through the windows, and a dining space is visible in the background.

5 out of 5 average rating, 25 reviews

Apartment In Point Breeze

This cozy unit is newly renovated and is a spacious upper unit in a duplex located in the Point Breeze section in the city of Pittsburgh, PA. The unit has 3 spacious bedrooms, 1 bathroom, an office, and a sunroom, board games, in-unit laundry, and keyless entry. This apartment is conveniently located less than a mile from grocery, shopping, restaurants, parks, and entertainment. It is also just a short distance to multiple universities, and many popular destinations.

Guest suite in Pittsburgh

A patio area is visible with a round white table surrounded by four metal chairs, shaded by a striped umbrella. A decorative bowl sits on the table. A barbecue grill is positioned beside a stone patio, with green lawn and trees in the background.

4.92 out of 5 average rating, 240 reviews

Renovated large private studio in Squirrel Hill

Cozy and lovely large studio with garden, separate private entrance, kitchen, and full bathroom. Located in the central and convenient neighborhood of Squirrel Hill, close to CMU, University of Pittsburgh and Chatham University, right next to Schenley Park and walking distance (only 2 blocks) to all the cafes, restaurants, shops, movie theater and local amenities of our amazing neighborhood. Downtown Pittsburgh is only 10-12 minutes drive.

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, 156 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.