Holiday rentals in Pleasant Hills

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Top-rated holiday rentals in Pleasant Hills

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

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Guest favourite
A nighttime view of Pittsburgh showcases a vibrant cityscape, with twinkling lights illuminating the skyline. The sloped foreground provides a natural boundary, creating a contrast against the urban setting. The scene captures the essence of life in a historically rich neighborhood.
Home in South Side Slopes
4.9 out of 5 average rating, 136 reviews

*z 2231 1BR Southside *Sloped* Home Close to Pgh

Quirky South Side Slopes home convenient to Pittsburgh and all local attractions. This property is located in one of Pittsburgh's original industrial neighborhoods which is remaking itself into a fun vibrant community. With fun views from high above the city this neighborhood was home to many Pittsburghers who worked in the steel mills that helped build our great nation. Come get a feel for the way Pittsburghers used to live and enjoy everything Pittsburgh has to offer today, yinzer approved!

Top guest favourite
A welcoming entryway features a small dining table beside a black couch adorned with cushions. Wall-mounted shelves showcase dishware and decorative items. Framed photographs hang on the wall, and a door with a window allows natural light to brighten the space.
Guest suite in West Mifflin
4.95 out of 5 average rating, 230 reviews

Hilltop Suite, Quiet Street

The suite has its own entrance in the back of the house and onsite parking in the driveway. You are in your own PRIVATE area that does not join with my living area in any way; we likely will never meet. The space is very updated and clean. Amenities include your own bathroom with a deluxe shower, an in-suite mini kitchen with stove and fridge, a small dining table, a couch, and a comfy queen bed. It’s approximately 15 mins to all main universities, the city center & all of the sports arenas.

Top guest favourite
A welcoming outdoor seating area is showcased with two individuals comfortably seated on a wooden swing. A guitar is hung on the brick wall behind them, adding a personal touch to this serene space.
Flat in Brentwood
4.97 out of 5 average rating, 359 reviews

Apartment: Home Sweet Home

Enjoy yourself in a quiet, bright, one floor living space, with a separate bedroom, (Queen Size bed), bathroom (shower) and living room. Sleeps 4 comfortably. Queen size sofa bed in living room sleeps 2. Private entrance with keyless entry, private off street parking. 6 miles from Downtown Pittsburgh sports, concerts and events. Close to shopping, pizza and restaurants. Uber available. Enjoy sweet bread or muffins with coffee or tea to begin your stay! We are happy to meet your needs!

Top guest favourite
A charming two-story cottage is nestled within lush greenery, showcasing a well-maintained exterior with a sloped roof and welcoming front porch. Vibrant flowers and shrubs surround the entrance, enhancing the peaceful outdoor ambiance. A clear blue sky complements the serene landscape.
Cottage in Bethel Park
5 out of 5 average rating, 124 reviews

"The Cottage on Summit"

The "Cottage on Summit" is charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . NOTE: A "request to book" will need additional information prior to "confirming by the host". Verified ID and at least ONE Positive review & No Negative reviews from previous stays are needed. House rules strictly enforced.

Top guest favourite
A comfortable living area features a dark leather sofa and an accent chair with a geometric pattern. Light spills in from a doorway leading to the dining area, where a wooden table is set for four. Decorative elements include a coffee table and wall art.
Home in Mt. Lebanon
4.97 out of 5 average rating, 447 reviews

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.

Guest favourite
A cozy living area is highlighted by a sleek beige leather sofa, accompanied by decorative pillows. A glass coffee table sits on an ornate area rug, while natural light illuminates the space. The staircase and a softly lit hallway can be seen in the background.
Home in Duquesne
4.91 out of 5 average rating, 282 reviews

Entire home near Kennywood without extra fees.

Bring everyone along for the trip, including Fido! Our home is a cozy, yet spacious Cape Cod southeast of downtown Pittsburgh. The backyard faces a beautiful and peaceful meadow. The yard is fenced in and has a small garden filled with herbs and tomatoes during the summer. Our home has all of the amenities to make your stay enjoyable and easy. We keep our home clean, organized and stocked with essentials. The beds, pillows and sheets are new and comfortable. Parking is plentiful and easy!

Guest favourite
The entrance features a brick facade with white shutters framing the window. A glass door is set within a wooden frame, leading to a deck area. The surroundings are lush with greenery, providing a welcoming touch to the space.
Home in Bethel Park
4.85 out of 5 average rating, 149 reviews

Cozy Home near DT PGH đŸ¶ friendly + fenced yard!

This cozy Cape Cod home was built in the 1950's but has many more modern updates. A full quarter acre FULLY FENCED backyard gives peace of mind to parents and pet parents regarding the safety and security. The home is only 10 miles from all of Pittsburgh's main attractions! It's also located in one of the safest neighborhoods in the PGH suburbs. A fully stocked kitchen, a 70-inch smart TV, and a ready-to-work office space awaits any guests who wish to experience a true local experience!

Guest favourite
Flat in Downtown Pittsburgh
4.95 out of 5 average rating, 110 reviews

Cozy 1BR Minutes from NFL Draft

Welcome to our newly remodeled 1 bedroom apartment, featuring modern furnishings, upscale appliances, and abundant natural light. Just steps from the David L. Lawrence Convention Center (DLCC), it's perfect for business travelers and event-goers. Enjoy nearby attractions like PNC Park, Market Square, and the Cultural District—all within walking distance. Whether you're visiting for business or leisure, our space provides a comfortable and convenient base for your Pittsburgh stay!

Guest favourite
A spacious living area features a plush, dark gray sofa set against a dark accent wall. A modern round mirror hangs above a light-colored coffee table, with a soft area rug beneath. The open kitchen is visible in the background, showcasing stainless steel appliances and bright cabinetry.
Flat in Friendship
4.96 out of 5 average rating, 188 reviews

Cozy King Bed Suite ~ Free Parking & Ground Floor!

Enjoy our cozy king bed suite located in the safe, central Friendship neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Whole Foods and short walk to Yinz Coffee shop! ⭐King bed (Memory foam mattress) ⭐Queen pull out bed ⭐Pack n play ⭐First floor w/ no steps ⭐In-unit washer/ dryer ⭐Large desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt!

Top guest favourite
An inviting living space features a brown leather sofa and a window adorned with dark curtains. Natural wood paneling enhances the cozy atmosphere, while a small Christmas tree adds a festive touch. The open layout connects to a dining area with wooden chairs and table.
Cabin in South Park Township
4.99 out of 5 average rating, 100 reviews

The Lily Pad Cabin

Cozy cabin offers open floor plan with covered porch overlooking small pond on our property. Uniquely decorated. Views of woods & fields, but close to numerous restaurants, parks & walking trails, & TRAX Farms. The Trolley to Pittsburgh is two minutes away. Should you need single night accommodation, please message me for consideration. Also consider “Mojo’s Loft”, our pet-friendly rental or Jackson Hill Cabin, our full log home with three bedrooms & a pool table.

Top guest favourite
The kitchen features modern stainless steel appliances, including a refrigerator and a gas range. Wooden cabinetry offers storage space, while a window allows natural light. A coffee maker and countertop accessories are also visible, with a soft rug positioned on the floor.
Apartment in Mt. Lebanon
4.92 out of 5 average rating, 181 reviews

Heart of Mt. Lebanon-Walk Anywhere-Easy 2 Downtown

Clean 2 Bedroom 1 Bathroom in the Heart of Mt. Lebanon. On the T line and minutes from Downtown Pittsburgh. 30 seconds walking to a microbrewery and a minute to all the Bars & Restaurants. This is a duplex that is Airbnb’d on the other side. Completely private entrance and unit. Amazing location and more intimate than the hotel up the street (Plus parking is free). Kitchen renovated. Well stocked with supplies. Has DirecTv and WiFi

Top guest favourite
A spacious living area features a large sectional couch facing a wall-mounted TV. The room is brightened by natural light coming through multiple windows. A modern kitchen is visible, equipped with stainless steel appliances. Decorative artwork adds character to the room.
Guest house in Mt. Lebanon
4.97 out of 5 average rating, 261 reviews

Cozy Mt Leb Carriage Hse | Kitchen | T to Stadium

Cozy 1 bedroom carriage house apt in Mt. Lebanon, fully-equipped kitchen, living room/dining room, separate bedroom and bathroom. Bedroom has a king size bed and couch is a large CB2 sectional. Keurig Coffee Maker with k cups. 1 car off street parking. Smart TV with Netflix and Amazon, also basic cable channels. Our guests love it! Please note there are 13 steps to the apartment - 8 concrete steps and 5 Wooden steps.

Popular amenities for Pleasant Hills holiday rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Pleasant Hills