Holiday houses 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
Apartment in Downtown Pittsburgh
4.9 out of 5 average rating, 269 reviews

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

LocationValueView

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.
Apartment in Pittsburgh
4.97 out of 5 average rating, 375 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!

ValueFamilyOutdoor spaces

Guest favourite
A cozy parlor is adorned with deep red walls and vintage decor. Two large velvet couches are positioned around a wooden coffee table. A vintage organ sits against one wall, complemented by a blue stained-glass light fixture overhead. Framed artwork and decorative elements enhance the unique atmosphere.
Apartment in Pittsburgh
4.94 out of 5 average rating, 108 reviews

The Weary Traveler

A haunting place for weary travelers that rests just above a curious little shop in the Allentown neighborhood of Pittsburgh. Established in 1903, the old bones of this building have a lot of magic hidden in them and the owners of The Weeping Glass have brought them back to life in this extension of their curiosity shop. Minutes from other off beat and unique businesses and a short ride to down town and the South Side. Please note that due to demand, our cancelation policy is extremely firm.

LocationValueCondition

Guest favourite
Guest suite in West Mifflin
4.95 out of 5 average rating, 258 reviews

Hilltop Suite, Quiet Street

You will have your own entrance & onsite parking in the driveway. Your PRIVATE area does not join with my living area in any way; we likely will never meet. The suite includes your own bathroom with a deluxe shower, an in-suite mini kitchen with stove & fridge, a small dining table, a couch, & a comfy queen bed. You control the temperature with your own HVAC system with both heating & cooling. It’s approximately 15 mins to all main universities, the city center & all of the sports arenas.

LocationValueOutdoor spaces

Top Guest favourite
Townhouse in Mt. Lebanon
4.99 out of 5 average rating, 181 reviews

Private Mt Lebanon Retreat Near Airport/Downtown

Welcome to your home away from home! This recently remodeled townhouse offers the perfect blend of comfort and style, situated just 20 minutes from the air port and city’s major stadiums. Ideal for all travelers, our home is nestled in a peaceful suburb with easy access to public transportation, nearby parks, and charming small businesses and shops. • Two bedrooms featuring king-sized beds. • An expansive kitchen, complete with peninsula and breakfast bar. We look forward to hosting you!

ValueFamilyAccess

Superhost
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
4.9 out of 5 average rating, 323 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!

LocationFamilyGetting around

Top Guest favourite
A bright living room highlights a modern sectional sofa adorned with yellow cushions, paired with a mid-century armchair. A wooden coffee table sits at the center, complemented by a woven area rug. Natural light filters through the windows, enhancing the inviting atmosphere.
Home in Mt. Lebanon
4.94 out of 5 average rating, 137 reviews

Cozy Bright Mt. Leb Cottage | 2 m to T to Stadiums

Relax with the whole family at this peaceful place to call your own. This lovely 3 bedroom cottage welcomes you and your guests in a private setting. This home has been updated and is a perfect place to feel right at home whether you are visiting family and friends or here on a business trip. Everything is here for you, from kitchen items, toiletries, washer and dryer and plenty of great outdoor areas to finish your evening on a great note. Lovely children's park down the street as well.

LocationFamilyHeating

Top Guest favourite
A single-story cottage is surrounded by greenery, showcasing a front porch with hanging plants. A gravel driveway leads to the side of the house. Natural light enhances the welcoming appearance of the exterior, blending harmoniously with the surrounding landscape.
Cottage in Boston
5.0 out of 5 average rating, 45 reviews

GAP Trail | Bike, Hike, Explore | Near Pittsburgh

All season cottage just a short walk with direct access to the Boston Trailhead on the Great Allegheny Passage. At Less than 20 miles (~40 min.) southeast of downtown Pittsburgh, it's an ideal home base for GAP Trail adventurers and regional travelers seeking a peaceful off the beaten path stay. A Short drive to groceries ,coffee shop, bakery, and dining. *Contact host for 1 day stays. *Kennywood Park-11mi *Golden Triangle Bike Rental-15mi *PNC Park-17mi *Point State Park-20mi

FamilyLocationSleep quality

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, 107 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.

ValueFamilyLayout

Top Guest favourite
A bright living room features a light-toned leather sectional sofa arranged around a coffee table. A stone fireplace is centered on the wall, flanked by audio equipment. Large windows allow natural light to fill the space, while wooden floors add warmth.
Home in Mt. Lebanon
4.96 out of 5 average rating, 102 reviews

Cozy house in the heart of Mt. Lebanon

Take a leisurely stroll through the quaint Mt Lebanon community, walk to the great restaurants Mount Lebanon has to offer, or walk to Hitchhiker and try one of the best local brews Pittsburgh has to offer. If you enjoy music or a movie, our stereo system will delight your ears. Our house is within walking distance to the Mt. Lebanon Library and the “T” which takes you to Station Square, Downtown Pittsburgh and the North Side.

FamilyLocationAir conditioning

Guest favourite
Apartment in Pittsburgh
4.96 out of 5 average rating, 72 reviews

A cozy furnished 1 bedroom lower level Apartment.

Cozy one bedroom, one bath fully furnished lower level apartment for rent. Private exterior entrance to this little slice of heaven will meet all the needs of a traveler looking for an extended stay or a short little trip to downtown . It is close to the many local attractions. 💫15 minutes to downtown. 💫Bus stop at front door. 💫Free on street parking. 💫The Breakfast Spot (walking distance)

FamilyValueBathroom

Guest favourite
A spacious living area is highlighted by a large sectional couch in neutral tones, accented with decorative pillows. A wooden coffee table sits in front, topped with a small plant and magazines. Light fills the room through windows, enhancing the open ceiling with exposed beams.
Apartment in Pittsburgh
4.91 out of 5 average rating, 98 reviews

Spacious & Bright Retreat – Perfect for Families!

Bring the whole family to this great place with lots of room for relaxation. We have designed this space to feel bright and open. The massive living room/dinning room is the centerpiece of this apartment with its comfy sectional couch and extra long table for dinner. The kitchen is fully equipped and has beautiful granite counters. Bedrooms are spacious with comfy beds. You will love it here!

LocationFamilyNearby

Popular amenities for Pleasant Hills holiday rentals