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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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, 223 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 Pittsburgh
4.97 out of 5 average rating, 358 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, 121 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.

Guest favourite
A spacious living room is filled with natural light, featuring a plush sofa and an eclectic area rug. An archway leads to a dining area with a round table surrounded by white chairs, complemented by greenery from nearby plants.
Home in Pittsburgh
4.78 out of 5 average rating, 218 reviews

✨Cozy & Stylish 2BR House 🏡 Sleeps 6✨Free Parking

*Only Out of Town Bookings please * Cheerful and stylish 2 bedroom home only 15 minutes to downtown Pittsburgh! Located in a charming neighborhood within walking distance to shops, restaurants, places of worship, Mt. Lebanon golf course and a grocery store. The house is also only a 5 minute walk to the T line which makes it easy to get into and out of downtown Pittsburgh! ⦿ 1 king bed ⦿ 1 queen bed ⦿ Queen sized sleeper sofa ⦿ Smart TV ⦿ Air conditioning ⦿ Off-street parking ⦿ Smart lock

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 Pittsburgh
4.97 out of 5 average rating, 444 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
4.92 out of 5 average rating, 267 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
A cozy living room is highlighted by an oversized leather sofa positioned across from a mounted television. A checkered rug anchors the space, which is adorned with a brick fireplace. Natural light filters through large windows, enhanced by light blue curtains, creating a welcoming environment.
Flat in Mount Washington
4.92 out of 5 average rating, 104 reviews

Off-street Parking | Retro 1-bed | Great Area

Welcome home to Mt. Washington! Inspired by the retro diners that make Pittsburgh unique, you'll find vintage & locally sourced details at every turn in our newly renovated, bright and cheery apartment. The spacious bedroom and living room provide more than enough space for 1-2 people. Enjoy breakfast from our fully-equipped kitchen, then have your coffee on our front deck, and enjoy Netflix from the couch. Our place also features one off-street parking spot (a real treat in Pittsburgh!)

Top guest favourite
A spacious living area features a comfortable sectional sofa and a pair of armchairs, accented by soft seating cushions. Large windows are adorned with sheer curtains, allowing natural light to brighten the room. A decorative area rug lies on the hardwood floor, and small tables complete the arrangement.
Home in Pittsburgh
5 out of 5 average rating, 125 reviews

Seneca Place: A historic home in Mount Lebanon.

Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

Top guest favourite
The image showcases a three-story home with a light grey exterior and blue accents, featuring a prominent gabled roof. A wooden deck with a railing extends in front, providing an inviting entryway. The neighborhood architecture is visible in the background.
Flat in Pittsburgh
4.98 out of 5 average rating, 168 reviews

Cute Apt Minutes from Downtown and Stadiums!

🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

Top guest favourite
A vintage desk is positioned by large windows adorned with golden curtains, allowing natural light to fill the space. A cozy ergonomic chair complements the desk, while a decorative globe and a small flower arrangement add character. The city skyline is visible through the window.
Flat in Mount Washington
4.97 out of 5 average rating, 164 reviews

Grandview Ave - King Bed - Spectacular Views!

One of the few furnished rentals on Grandview Ave, the famous road with million dollar views in Pittsburgh! Completely remodeled to the studs as a short-term rental, our place exudes Pittsburgh charm. Work from home with spectacular views of the city from your vintage desk, relax on the couch and watch the 60" TV, or just hang out on the king size bed! We're just a block from Shiloh St., with 10+ bars & restaurants, but you're always able to cook at our fully stocked kitchen!

Top guest favourite
A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.
Home in East Carson Street
4.91 out of 5 average rating, 420 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
A cozy seating area is featured, with a dark gray sofa adorned with striped pillows. A small coffee table sits in front, and a bright workspace is visible nearby, complete with a desk and chair. Natural light pours through large windows covered with sheer curtains.
Flat in Friendship
4.89 out of 5 average rating, 241 reviews

PRIVATE FULL STUDIO (G2)

This Studio is for anyone needing a neat, clean, cool place to stay with a queen bed, a sleeper sofa (almost queen size), a full kitchen and a full bathroom (shower only) with a private entrance on the 2 nd 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)

Popular amenities for Pleasant Hills holiday rentals