House holiday rentals in Shadyside, Pittsburgh

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Top-rated house rentals in Shadyside, Pittsburgh

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite

Home in North Side

4.93 out of 5 average rating, 164 reviews

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Guest favourite

Home in Bloomfield

4.96 out of 5 average rating, 205 reviews

Spacious Luxury 6 BR Art Deco Home In The City

Location & Luxury! This meticulously renovated, spacious six bedroom home is nestled between Shadyside, North Oakland & Bloomfield! Coffee lovers will enjoy our curated coffee bar selections. Travel light, we provide linens, toiletries & a fully equipped chef's kitchen. Our space is great for families touring universities in Oakland, groups coming for concerts & events or travelers just looking to stay close to everything! -close to major universities -easy drive to North Shore destinations

Guest favourite

Home in Squirrel Hill North

4.87 out of 5 average rating, 104 reviews

Hot Tub Infrared Sauna Peloton treadmills

Eco-conscious luxury vacation rental one block from the Carnegie Mellon University campus, newly renovated and furnished. Features hardwood floors, natural latex mattresses, organic cotton and linen bedding, original artwork, fast Wi-Fi, and a 77" OLED 4K TV. Minutes from the University of Pittsburgh, the Carnegie Museums, Schenley Park, and Phipps Conservatory. The house sleeps up to 13 adults. Off-street parking is available 1-2 cars. 7-night minimum stay required for Pitt & CMU graduation.

Top guest favourite

Home in Lower Lawrenceville

4.97 out of 5 average rating, 142 reviews

Off-Street Parking, Steps to Butler St., Patio!

In the heart of lower Lawrenceville, our place exudes historic Pittsburgh charm while providing an incredibly cozy experience. Our spacious kitchen invites you to cook a great dinner. Our comfortable living room surrounded by historic brickwork + open staircase encourages you to relax and watch Netflix. The patio welcomes you with fresh air. With two full bathrooms, two couples or a family can get ready for the day (or night!) Within walking distance, bars, breweries, and restaurants abound!

Top guest favourite

Home in Friendship

4.97 out of 5 average rating, 102 reviews

Sunny, Creative Duplex in Friendship

You and your travel companions will be in an ideal Pgh spot when you stay at this Friendship neighborhood home. With 3 floors, you'll have lots of room to spread out or gather together. This beautifully updated 100-year-old home is a creative space, filled with art from Pgh artists, cheery textiles from around the world, and vintage decor scattered throughout. It’s a charming retreat for artists & writers, a cozy spot for families, or the perfect place for larger groups to share a getaway.

Guest favourite

Home in Squirrel Hill South

4.93 out of 5 average rating, 320 reviews

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.

Top guest favourite

Home in Central Lawrenceville

4.98 out of 5 average rating, 179 reviews

Perfect Location in Lawrenceville: Top 10 airbnb

Named Top Ten Trendiest AirBnB's in Pgh Dec. 2021 by Living Pittsburgh! Beautifully renovated three story brick row house built in 1890 - perfect location a few hundred feet from Butler Street in Lawrenceville. Gorgeous street - very safe area. 2 miles from downtown Pgh. Street parking. Entry keypad. Private outdoor area with seating. French bakery, tons of restaurants & shops right out the front door. You couldn't find a better location in L-ville - our favorite neighborhood in PGH!

Guest favourite

Home in Central Lawrenceville

4.96 out of 5 average rating, 194 reviews

Willy Wonka Themed | King Bed | Free Parking | Arc

✓ Willy Wonka Themed ✓ Free Parking ✓ 1 Minute Walk to Children’s Hospital ✓ King Bed – 6 total beds ✓ Arcade / BBQ / Fire Pit / Patio w/ String Lights ✓400 mbps Fast Wi-Fi ✓ 12-inch cooling gel memory foam Rank One Stays presents Pure Imagination - You’ll explore the world of Wonka complete with oversized gummy bears, lollipops, and a wondrous boat in a completely unique, interactive and immersive Wonka experience just minutes away from Acrisure, PNC Park, PPG Arena, and Downtown.

Guest favourite

Home in Bloomfield

4.92 out of 5 average rating, 197 reviews

Urban serenity, privacy in charming carriage house

Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

Guest favourite

Home in Shadyside

4.89 out of 5 average rating, 161 reviews

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!

Guest favourite

Home in South Side Flats

4.91 out of 5 average rating, 396 reviews

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).

Guest favourite

Home in Friendship

4.88 out of 5 average rating, 503 reviews

PRIVATE MINI STUDIO (D2)

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).