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Vacation rentals in Squirrel Hill

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Top-rated vacation rentals in Squirrel Hill

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Townhouse in Pittsburgh

4.84 out of 5 average rating, 294 reviews

Private bath 1st floor suite in Squirrel Hill

Situated in the heart of Squirrel Hill, all sorts of dining, theater, shopping and parks are within a safe walking distance. Explore the incredible variety of Chinese, Korean, Mexican, Jewish, Italian, Indian foods that reside in our neighborhood. CMU, Pitt, Chatham, Duquesne & Oakland are close by but why go anywhere else when all you need is right here. Pittsburgh's famous Frick Park w/ endless trails is under a mile. Schenley Park is under 20 min walk. Phipps Conservatory a 7 min drive.

Guest suite in Pittsburgh

4.98 out of 5 average rating, 192 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Home in Pittsburgh

4.93 out of 5 average rating, 298 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.

Rental unit in Pittsburgh

4.96 out of 5 average rating, 458 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Rental unit in Pittsburgh

4.9 out of 5 average rating, 124 reviews

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

Rental unit in Pittsburgh

4.9 out of 5 average rating, 115 reviews

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

Unique and family oriented modern 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.

Home in Pittsburgh

4.9 out of 5 average rating, 378 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).

Rental unit in Pittsburgh

4.98 out of 5 average rating, 129 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!

Guest suite in Pittsburgh

4.89 out of 5 average rating, 364 reviews

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).

Guest suite in Pittsburgh

4.91 out of 5 average rating, 220 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.

Guest suite in Pittsburgh

4.98 out of 5 average rating, 189 reviews

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Rental unit in Pittsburgh

4.94 out of 5 average rating, 381 reviews

Cozy Entire Apt 2 *Friendship Park* free parking

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. The apartment was recently updated and feels fresh, spacious and blue flair. This 2nd floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

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Popular amenities for Squirrel Hill vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Squirrel Hill

Rental unit in Pittsburgh

5 out of 5 average rating, 16 reviews

Lamont Place

Home in Pittsburgh

5 out of 5 average rating, 62 reviews

Luxe 5B/2.5B | Off St. Parking | Family-Friendly

Rental unit in Pittsburgh

4.91 out of 5 average rating, 11 reviews

1st Fl. Huge Flat on 2 Acres - Pets/Garage Parking

Rental unit in Pittsburgh

4.99 out of 5 average rating, 69 reviews

2bd unit in regent square

Rental unit in Pittsburgh

5 out of 5 average rating, 60 reviews

Lavish Squirrel Hill - 3rd Floor

Home in Pittsburgh

4.97 out of 5 average rating, 31 reviews

Upscale spacious kid-friendly home, amazing views!

Rental unit in Aspinwall

4.98 out of 5 average rating, 57 reviews

Aspinwall 1 bedroom Apartment

Home in Pittsburgh

4.95 out of 5 average rating, 41 reviews

Off-Street Parking, 2 Full Baths, Great Patio!

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