Family-friendly holiday rentals in Squirrel Hill

South Side Flats - Central to everything!

Artfully decorated, large, and open concept 1 bedroom apartment in the center of the South Side Flats entertainment district. Everything you need is within steps of your front door - restaurants, grocery, and entertainment. 5 min from downtown & within 15 min to anywhere in the city. IMPORTANT: This listing is exclusively for people visiting Pittsburgh. DO NOT book with us if you live in Allegheny County without 1st receiving permission from the host, or your reservation will be cancelled.

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.

Entire private floor (giant Jacuzzi with shower!)

Welcome! In addition to having numerous "sparkling clean" reviews, I am committed to helping Airbnb guests stay safe by cleaning and disinfecting frequently touched surfaces. This is a finished basement in my house with its own entry way. Being below ground helps keep things cool in the summer. Off-street parking pad available in back of house (look for small Amish shed). Safe, quiet, and family-oriented neighborhood minutes from the Zoo, Highland Park, and downtown!

Luxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks

Pittsburgh's premier, top of the line Airbnb! No expense was spared outfitting our 4 bedroom, 2.5 bath home! Amenities galore both indoors & out with 3 large outdoor spaces, fire pit, and garage parking. Every high end detail has been meticulously selected and designed. Take advantage of all the city of Pittsburgh has to offer in the lap of luxury with your own centrally located private residence on the North Side, complete with a Peloton for the healthy-minded!

PRIVATE MINI STUDIO (D1)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd 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).

Large victorian 3rd flr apt in walkable eastend

An entire third floor apartment of a historic Colonial Revival house in the Friendship neighborhood. Two bedrooms, each with a firm queen memory foam bed, one bathroom with claw foot tub/shower, huge living room with seating area and desk, and a fully equipped kitchen with washer and dryer. Walk up to third floor. A queen air mattress bed or pack n' play can be added to any one of the bedrooms or the living room, just let us know.

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

Newly remodeled house in the Squirrel Hill neighborhood of Pittsburgh! Includes everything you need for a comfortable stay with friends & family. 🔑 4 BR/2.5 BA - Comfortably Sleeps 8 🔑 Self Check-in 🔑 Private Parking for 2 + Free Street Parking 🔑 Fully Equipped Kitchen w Brand New Appliances 🔑 Quiet Residential Street in the Quaint Neighborhood of Squirrel Hill 🍁 FRICK Park within Steps of your front door

Apt 6 Bloomfield/Lawrenceville private mini studio

This Mini Studio is a clean, cool place to stay. Located in one of the best spots for work or play. Freshly remodeled & Fully furnished with queen bed, full bathroom, smart HDTV, free wifi, cable. Place is close to the city center, art and culture, nightlife, public transport and parks. You would love the location, the coziness. The apartment has a full kitchen with all needed essentials.

Renovated top floor unit! Close to downtown!

Bright, completely renovated, top floor unit in an historical neighborhood of Pittsburgh! Close enough to walk to the both Heinz Field and PNC Park stadiums, and Rivers Casino. Lot's of charm and character! Located 5-10 minutes from downtown and convention center via car, or take the bus right from the corner. Please note this is a third floor walk up, so please be comfortable with steps!