Holiday Rentals in Pittsburgh, PA

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Pittsburgh, PA holiday rentals
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Best Holiday rentals and Airbnb offers in Pittsburgh, PA

Best family friendly Pittsburgh, PA holiday rentals

Among the 3853 accommodations in Pittsburgh, PA, here are the 4 best family friendly rentals

Modern Apt W/ Hulu, Gym & Parking Near Restaurants - Pittsburgh, PA
10 51 reviews
Pittsburgh, PA
27/06 – 04/07
SG$263/nighttotal: SG$1841 (7 )

Modern Apt W/ Hulu, Gym & Parking Near Restaurants

1 2
apartment , Pittsburgh
This one-bedroom Pittsburgh apartment, ideally located near Walnut Street, offers easy access to shops, restaurants, West Penn Hospital, and the University of Pittsburgh Medical Centre, all within a short distance.
The self-contained flat sleeps three, boasts a fully equipped kitchen with a rice cooker and coffee machine, a 50" Smart TV with premium streaming services, in-unit laundry, and access to building amenities including a fitness centre, co-working spaces, and an EV charging station.
Ohio River Valley Views In The City! - Pittsburgh, PA
9.9 112 reviews
Pittsburgh, PA
12/07 – 17/07
SG$396/nighttotal: SG$1980 (5 )

Ohio River Valley Views In The City!

1 6
apartment , Pittsburgh
This Grandview house, a short 1.6km walk from the Monterrey Bay Fish Grotto and minutes from Pittsburgh city centre, offers a blend of rural charm and urban convenience.
Sleeping six guests across three bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, multiple outdoor decks with fire pits, high-speed Wi-Fi, free garage parking, and family-friendly amenities including a travel cot, high chair and baby gates.
View From The Top!  Steps From Grandview, Sleeps 8 - Pittsburgh, PA
10 76 reviews
Pittsburgh, PA
24/11 – 01/12
SG$432/nighttotal: SG$3024 (7 )

View From The Top! Steps From Grandview, Sleeps 8

4 3
apartment , Pittsburgh
This apartment is located in Mount Washington, a half-kilometre from the Mount Washington Overlook and a short distance from the Shiloh Market District, a lively area with restaurants, pubs, and shops. It has received excellent user ratings.
The apartment has four bedrooms and two bathrooms, comfortably accommodating up to eight guests. It offers a range of amenities, including a fully equipped kitchen, a private deck, a 55-inch TV, high-speed internet, and parking.
Cozy House In The Heart Of Mt. Lebanon - Pittsburgh, PA
9.9 96 reviews
Pittsburgh, PA
01/08 – 31/10
SG$225/nighttotal: SG$20475 (91 )

Cozy House In The Heart Of Mt. Lebanon

3 2
apartment , Dormont
This three-bedroom flat is situated in Mount Lebanon, a short walk from the T station that connects to Pittsburgh city centre.
The property offers a fully-equipped kitchen, a private garden, and a jacuzzi, making it ideal for families or groups of up to six people.

Best Pittsburgh, PA holiday rentals with parking

3 Br - Off Street Parking - Amazing View Nearby - Pittsburgh, PA
9.1 308 reviews
Pittsburgh, PA
17/07 – 19/07
SG$361/nighttotal: SG$722 (2 )

3 Br - Off Street Parking - Amazing View Nearby

3 3
apartment , Pittsburgh
This apartment is located in Pittsburgh, just 3.9 kilometres from Heinz Field and 4.5 kilometres from the Pittsburgh Children's Museum, making it ideal for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This apartment offers a comfortable and convenient stay with a fully equipped kitchen and a washing machine. Guests can enjoy amenities such as a terrace, garden, parking, and free Wi-Fi, ensuring a pleasant and relaxing experience.
Dormont Pittsburgh 1a Bright And Cozy Studio Apartment With Free  Parking - Pittsburgh, PA
10 1 review
Pittsburgh, PA
27/06 – 04/07
SG$250/nighttotal: SG$1750 (7 )

Dormont Pittsburgh 1a Bright And Cozy Studio Apartment With Free Parking

1 2
studio , Pittsburgh
This modern studio apartment is situated in the Beechview/Dormont area, offering a 10-minute drive to Pittsburgh's iconic overlooks and an 11-minute drive to Downtown, with local shops and eateries just a 3-minute walk away.
This well-appointed accommodation for two guests includes a Queen bed, a full bathroom, a fully equipped kitchen with a fridge, microwave, and dishwasher, high-speed WiFi, a 50-inch Smart TV, and an in-unit washer/dryer, with free street parking available.
Bloomfield, Pittsburgh Large And Accessible 3bedorom Apartment With Free Parking - Pittsburgh, PA
9.0 12 reviews
Pittsburgh, PA
08/08 – 09/09
SG$204/nighttotal: SG$6528 (32 )

Bloomfield, Pittsburgh Large And Accessible 3bedorom Apartment With Free Parking

3 1
apartment , Pittsburgh
This Bloomfield flat is conveniently located in Pittsburgh, Pennsylvania, minutes from UPMC Children's Hospital and offering easy access to the universities and Lawrenceville.
The three-bedroom property sleeps seven guests, includes a fully equipped kitchen, laundry facilities, free parking, and a 55-inch smart TV, perfect for families visiting the city.
Cozy 1br Retreat Near Highland Park & Zoo - Pittsburgh, PA
9.0 2 reviews
Pittsburgh, PA
10/07 – 15/07
SG$207/nighttotal: SG$1035 (5 )

Cozy 1br Retreat Near Highland Park & Zoo

1 2
apartment , Pittsburgh
This Highland Park flat is situated approximately 8 km from the Pittsburgh Zoo & PPG Aquarium, 21 km from the city centre, and 21 km from local universities.
The two-bedroom, one-bathroom property sleeps five, boasting a fully equipped kitchen, smart TV, free street parking, and is within walking distance of local eateries and a coffee shop.

Frequently asked questions about holiday rentals in Pittsburgh, PA

  • What should a first-time visitor not miss in Pittsburgh, PA?

    You absolutely must visit the Carnegie Museum of Natural History, with its dinosaur skeletons and impressive collection. The Andy Warhol Museum is also a must-see, showcasing the work of one of Pittsburgh's most famous sons. And, of course, no trip to Pittsburgh is complete without a ride on the Duquesne Incline, offering stunning views of the city.
  • What are the best Airbnb and vacation rentals in Pittsburgh, PA?

    3e *New* Huge Spacious 3 Bedroom In Oakland That Sleeps 12, Luxury Pittsburgh Grandview Ave Apt and Pittsburgh's Only Tiny House are the most popular Airbnb and vacation rentals in Pittsburgh, PA among travelers.

  • Which neighborhood in Pittsburgh, PA should you consider for a vacation rental?

    The Strip District is a vibrant area with lots of restaurants and shops, but it can be noisy at night. Lawrenceville is a bit quieter, with trendy restaurants and bars, and is close to the city centre. If you want to be near the action, then the South Side Flats is the place to be, with its nightlife and proximity to the stadiums.
  • What are the most popular Airbnbs in Pittsburgh, PA?

    Among the Airbnbs in Pittsburgh, PA, City View King Bed At Pittsburgh Downtown, Pittsburgh's Only Tiny House and Luxury Pittsburgh Grandview Ave Apt are the most popular ones.

  • What are the top family-friendly attractions in Pittsburgh, PA?

    The Pittsburgh Zoo & PPG Aquarium is always a hit with families. The Carnegie Science Center is another great option, with interactive exhibits and a planetarium. And for a bit of fun, the Phipps Conservatory and Botanical Gardens is a lovely place to spend a few hours.
  • What are the best vacation rentals with a pool in Pittsburgh, PA?

  • When is the best time to book a vacation rental in Pittsburgh, PA?

    The best time to book a vacation rental in Pittsburgh is during the shoulder seasons, April-May and September-October, when the weather is still pleasant but the crowds are smaller. You can also find good deals during the winter months, but be prepared for colder weather.
  • What are the best rentals for families and kids in Pittsburgh, PA?

  • What events or festivals should visitors check out in and around Pittsburgh, PA?

    The Three Rivers Arts Festival in June is a great event with live music, art installations, and food stalls. The Pittsburgh Pride Festival in June is a colourful celebration of diversity. And for a unique experience, check out the Picklesburgh festival in July, celebrating all things pickle.
  • What are the best rentals or Airbnbs with a jacuzzi in Pittsburgh, PA?

  • What are the best budget-friendly activities in Pittsburgh, PA?

    Take a walk or bike ride along the Three Rivers Heritage Trail, which runs through the city centre and offers stunning views of the rivers. Visit the free museums in the Oakland neighbourhood, including the Carnegie Museum of Art and the Carnegie Museum of Natural History. And don't forget to check out the free concerts and events held in the city parks throughout the summer.
  • What are the best restaurants with local dishes in Pittsburgh, PA?

    For a classic Pittsburgh experience, try the Primanti Bros. sandwiches, piled high with meat, cheese, and fries. The Pittsburgh-style hot dog, topped with coleslaw and french fries, is another local favourite. And for a taste of the city's Italian heritage, check out one of the many Italian restaurants in the Strip District.
  • What are the best walking or cycling routes in Pittsburgh, PA?

    The Great Allegheny Passage is a popular cycling route that runs from Pittsburgh to Cumberland, Maryland. The Three Rivers Heritage Trail is a great option for a leisurely walk or bike ride through the city centre. And for a scenic walk, try the Mount Washington Trail, which offers stunning views of the city.
  • Are there pet-friendly attractions in Pittsburgh, PA?

    Many of the city parks are pet-friendly, including Schenley Park and Highland Park. Some restaurants also have outdoor seating areas that are pet-friendly. Check the websites of individual attractions to confirm pet policies.
  • What are the benefits of choosing a vacation rental in Pittsburgh, PA?

    Vacation rentals offer more space and privacy than a hotel room, and often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Pittsburgh, PA?

    Pittsburgh is a city known for its sports teams, including the Pittsburgh Steelers (American Football), Pittsburgh Pirates (Baseball), and Pittsburgh Penguins (Ice Hockey). You can catch a game at Heinz Field, PNC Park, or PPG Paints Arena, respectively.

Destinations nearby

Best Pittsburgh, PA holiday rentals with a balcony

Spacious And Modern Three Bedroom Apartment In Pittsburgh, Free Street Parking - Pittsburgh, PA
Pittsburgh, PA
12/07 – 17/07
SG$416/nighttotal: SG$2080 (5 )

Spacious And Modern Three Bedroom Apartment In Pittsburgh, Free Street Parking

3 6
apartment , Pittsburgh
This family-friendly flat in Pittsburgh's North Side is conveniently located a short drive from Station Square and The Waterfront for shopping, and offers easy access to PNC Park and PPG Paints Arena.
This spacious three-bedroom, two-bathroom apartment accommodates up to seven guests and features a full kitchen with a dishwasher, a deck, high-speed internet, and a Smart Home Security system, with access to the second and third floors requiring the use of stairs.
Perfect Pittsburgh Home Close To City & Airport - Pittsburgh, PA
9.3 227 reviews
Pittsburgh, PA
01/08 – 06/03
SG$169/nighttotal: SG$36673 (217 )

Perfect Pittsburgh Home Close To City & Airport

1 2
house , Crafton
This charming one-bedroom house is located just 4.3 miles from the Pittsburgh Children's Museum and 4.5 miles from PNC Park, offering easy access to the city's attractions while providing a peaceful retreat from the hustle and bustle. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The 39 square metre property comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio, and a garden. Amenities include air conditioning, free Wi-Fi, a TV, and parking, ensuring a comfortable and enjoyable stay.
Hostwise Stays  2 Apartments In 1 - Great Privacy, Beautiful Space! - Pittsburgh, PA
9.6 18 reviews
Pittsburgh, PA
20/07 – 21/07
SG$411/nightfor 1 night

Hostwise Stays 2 Apartments In 1 - Great Privacy, Beautiful Space!

3 2
apartment , Pittsburgh
This Upper Hill property is conveniently located less than 1.3km from the Pittsburgh Ballet Theatre and within 4.8km of the University of Pittsburgh, PPG Paints Arena, Carnegie Mellon University, and PNC Park.
This three-bedroom, two-bathroom house sleeps five guests and offers a fully equipped kitchen, free Wi-Fi, a private balcony, and a peaceful garden; explore nearby attractions including the universities and sporting venues.
Urban Retreat With Garage On Mt. Washington - Pittsburgh, PA
9.9 236 reviews
Pittsburgh, PA
17/07 – 19/07
SG$435/nighttotal: SG$870 (2 )

Urban Retreat With Garage On Mt. Washington

3 4
apartment , Pittsburgh
This Mount Washington holiday home boasts stunning city views and is located 0.6km from the Monongahela Incline, providing easy access to downtown Pittsburgh and attractions such as PPG Paints Arena and PNC Park (within 4.8km).
The 123 square metre property sleeps six guests in two bedrooms and features a fully equipped kitchen, swimming pool, spa, and private garden, alongside free Wi-Fi.

Best Pittsburgh, PA holiday rentals with air conditioning

Shadyside/pittsburgh, Modern & Unique 1bd W/prkng - Pittsburgh, PA
9.7 260 reviews
Pittsburgh, PA
02/07 – 05/07
SG$344/nighttotal: SG$1032 (3 )

Shadyside/pittsburgh, Modern & Unique 1bd W/prkng

1 1
apartment , Pittsburgh
This Shadyside flat is centrally located in Pittsburgh, offering easy access to UPMC Hospitals and Walnut Street, with numerous shops and restaurants nearby.
The one-bedroom apartment sleeps three, features a full kitchen with dishwasher, in-unit laundry, a 55-inch Smart TV, and high-speed internet; free parking is provided.
Backyard Deck☀️bbq🍖parking✨allegheny Gen.🏥quiet - Pittsburgh, PA
9.8 274 reviews
Pittsburgh, PA
12/07 – 17/07
SG$290/nighttotal: SG$1450 (5 )

Backyard Deck☀️bbq🍖parking✨allegheny Gen.🏥quiet

1 6
apartment , Pittsburgh
This three-bedroom flat is situated in Pittsburgh's Northside neighbourhood, a historic district built after the Civil War, just a short distance from Allegheny General Hospital. It has received excellent ratings for user experience, location, and cleanliness.
The property is spacious and comfortable, accommodating up to eight guests. It comes equipped with modern appliances, a private outdoor space with a dining area and barbecue, and free on-street parking.
Open Floor Spacious Home, 15min From Downtown, Private Garage, Kids Friendly - Pittsburgh, PA
8.9 65 reviews
Pittsburgh, PA
14/08 – 17/08
SG$387/nighttotal: SG$1161 (3 )

Open Floor Spacious Home, 15min From Downtown, Private Garage, Kids Friendly

3 2
house , Pittsburgh
This recently renovated Pittsburgh holiday home is situated approximately 8.9 kilometres from Downtown Pittsburgh, offering convenient access to Point State Park, PNC Park, and the Andy Warhol Museum.
The 106-square-metre property sleeps six comfortably, boasting three bedrooms, one bathroom, a fully equipped kitchen with dishwasher, private parking, Wi-Fi, and a private patio; nearby attractions include hiking trails and a water park.
Modern Blue Apartment W/ Parking, W/d + Smart Tvs - Pittsburgh, PA
9.6 44 reviews
Pittsburgh, PA
01/08 – 06/03
SG$125/nighttotal: SG$27125 (217 )

Modern Blue Apartment W/ Parking, W/d + Smart Tvs

1 2
apartment , Pittsburgh
This newly updated flat is situated in Pittsburgh's historic Observatory Hill district, placing you within 4 kilometres of downtown, a short drive to Acrisure Stadium and PNC Park, and a convenient distance to Riverview Park, with excellent links to major motorways.
This accommodation offers a stylish and modern living space for up to five guests, featuring two bedrooms and one bathroom, complete with air conditioning, Wi-Fi, and a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher, plus off-street parking.
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