House holiday rentals in Squirrel Hill

Skyline Haven:5BR/3.5BA +2 parking spots + Rooftop

Experience unparalleled luxury in this spacious 5-bedroom, 3.5-bathroom haven, perfectly situated in the heart of Pittsburgh. Boasting not one, but two roof decks, you'll have the finest city vistas right at your fingertips. Relax by the indoor-outdoor gas fireplace this is a serene escape amidst the urban hustle. With the addition of garage parking for 1 vehicle + Parking pad directly in front of the garage door, your downtown retreat combines modern elegance with supreme comfort, promising a m

King Bed | Free Parking | Arcade | Fire Pit

✓ King Bed, 2 queen, 1 rollaway twin ✓ Free parking ✓ On Carson St-nightlife & entertainment district ✓ Arcade / Fire Pit / Patio ✓ White noise machines ✓ 10 mins to Acrisure, PNC Park, PPG Rank One Stays presents, Dacha, a charming urban retreat in the heart of Pittsburgh's vibrant Southside neighborhood! This hidden gem has been thoughtfully designed to capture the cozy essence of a cabin while offering all the modern amenities you crave. Book your stay today & experience it for yourself!

Your Home Away from Home in Pittsburgh's East End!

This bright, stylish, and comfortable space, designed by an HGTV producer! With a fully remodeled kitchen and bathroom, cozy beds, and inviting rooms, this home offers the perfect home away from home. Conveniently located within 20 minutes of everything Pittsburgh has to offer, including sports fields, rivers, bridges, shopping, museums, historical sites, music venues, universities, and more! Whether you're here for business or pleasure, you'll find everything you need for a relaxing stay.

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

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.

Luxury Row House ❤️️of Lawrenceville. 10 min to DT

Enjoy urban living in this designer-furnished modern private house on a quiet residential street, a few steps from Butler St and all the nearby boutiques, cafes, bars & restaurants. Our cozy home is a perfect mix of modern finishes and original early 20th Century Steel Era features. Ideal for groups/solo travelers & romantic getaways in the city. Under 10 min drive to DT, Strip District, stadiums (Acrisure/Heinz, PNC Park, PPG Paints), universities & 10 min walk to Children's Hospital.

3 BR home~Steps from Walnut Street~Free parking

Beautiful 3 Bed / 2 Bath home in the heart of Shadyside! This home is located STEPS away from popular Walnut Street, which has plenty of fun restaurants, shops and more! 💫Four memory foam beds (2 king/ 2 queen) 💫Twin-sized rollaway bed 💫Pack N' Play crib 💫Two full bathrooms 💫Free Off street parking 💫Private front and back patio 💫Free in-unit washer/ dryers 💫Fully stocked & equipped kitchen My team and I are here for you 24/7 before, during and after your stay with us!

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Fire Pit + Family Friendly + Great Location!

Welcome to our family-friendly home in Bloomfield! Tickle the ivories on our baby brand piano while you send the kids upstairs to play with coloring books, toys, and more. Cook a great meal in our well stocked kitchen, or relax on the couch and watch Netflix. At night, spark up the fireplace and enjoy an evening outside with friends! If you're an "out and about" type - you're just a few blocks from the main drag in Bloomfield, full of great bars & restaurants!