House holiday rentals in Penn Hills

4.92 out of 5 average rating, 114 reviews

The exterior of a four-story home is depicted, featuring a light-colored facade with multiple windows. A well-maintained pathway leads to a double-door entrance framed by two symmetrical awnings. Lush green shrubs and trees provide a natural border, enhancing the serene ambience of the setting.

Home in Shadyside

Stunning 4-story Home | Sauna | Parking | Walkable

Welcome to our stunning & secluded 4-story home! This home is huge w/ 4 BRs and 2.5 baths, perfectly located in the heart of Shadyside. Short walk of plenty of restaurants, coffee shops, bars, shops, and steps away from Giant Eagle Market District! ⭐4 beds with memory foam mattresses (2 King / 2 Queen) ⭐Sauna ⭐2 private decks ⭐Futon + air mattress + 1 rollaway bed + 1 crib ⭐Washer/ dryer ⭐Off-street parking(3 cars) My team and I are here for you 24/7 before, during and after your stay with us!

4.95 out of 5 average rating, 180 reviews

A modern living room features large windows that allow natural light to fill the space. A sleek gas fireplace is framed by dark stone, while a large television is mounted on the wall. Comfortable armchairs and a circular coffee table complete the inviting atmosphere.

Home in Strip District

Skyline Haven:5BR/3.5BA +2 parking spots + Rooftop

Experience unparalleled luxury in this spacious 5-bedroom, 3.5-bathroom haven, perfectly situated in the heart of Pittsburgh. Boasting not one, but two roof decks, you'll have the finest city vistas right at your fingertips. Relax by the indoor-outdoor gas fireplace this is a serene escape amidst the urban hustle. With the addition of garage parking for 1 vehicle + Parking pad directly in front of the garage door, your downtown retreat combines modern elegance with supreme comfort, promising a m

A modern living area is showcased with a dark blue accent wall. A large flat-screen TV displays mountain scenery above a stylish console table. A decorative plant adds a touch of greenery, while a clock is positioned above the staircase, enhancing the contemporary design.

4.99 out of 5 average rating, 112 reviews

Terry’s Place

~Newly updated duplex ~Fully equipped kitchen with all new appliances ~Spacious 4 bedroom 2 bathrooms ~Located the heart of Pittsburgh in the neighborhood of Mt Washington ~20 minute drive to the Pittsburgh International Airport ~6 minute drive to downtown ~10 minute drive to: PPG Paints Arena Acrisure Stadium PNC park David L. Lawrence Convention Center Duquesne University ~12 minutes drive to the University of Pittsburgh ~2 blocks away from the historic overlook of the city & Duquesne Incline

4.93 out of 5 average rating, 282 reviews

A functional kitchen features grey cabinets complemented by wooden countertops. Open shelves display various glassware and kitchen essentials. A large sink with a dish drying rack is visible, alongside modern appliances, including a stainless steel refrigerator and coffee maker. Natural light enters through a window with blinds.

Home in North Side

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

A cozy living area features a colorful array of artwork on the walls and a mounted flat-screen television. A decorative fireplace with a warm glow is complemented by a cowhide rug on the wooden floor. A leather recliner and a dining area are seen in the background.

4.81 out of 5 average rating, 255 reviews

Steel City Beds, Breakfast and More

3-story single family home in Pittsburgh's popular eastend. Common areas decorated with eclectic mix of outsider and emerging art, art deco collectibles and antiques. Inviting outdoor spaces including front porch, fenced in backyard and play area good for kids and pets. Short walk to public transit, coffee shops, fine-dining, food coop, Construction Junction architectural artifacts, historic Frick Mansion and more. 5 minute drive or Uber ride to 4 premier shopping and entertainment centers.

The exterior of the historic log house is visible, showcasing its rustic charm with exposed logs. Vibrant foliage in shades of red and orange surrounds a furnished porch, while fallen leaves blanket the ground. The entrance is accessible via a small set of stairs.

4.86 out of 5 average rating, 333 reviews

Wyckoff-Mason Log House 1774 Historic Landmark

Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

4.98 out of 5 average rating, 113 reviews

A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.

Home in Shadyside

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

4.88 out of 5 average rating, 161 reviews

Home in Forest Hills

East End Gem | Your Home Away from Home

This bright, stylish, and comfortable space, designed by an HGTV producer! With a fully remodeled kitchen and bathroom, cozy beds, and inviting rooms, this home offers the perfect home away from home. Conveniently located within 20 minutes of everything Pittsburgh has to offer, including sports fields, rivers, bridges, shopping, museums, historical sites, music venues, universities, and more! Whether you're here for business or pleasure, you'll find everything you need for a relaxing stay.

The exterior showcases a charming three-story home with a distinctive architectural design. Its light-colored brick facade is accented by purple trim. Lush green foliage surrounds the entrance, which features steps leading up to a welcoming porch with colorful potted flowers.

4.98 out of 5 average rating, 161 reviews

Sunny, Creative Duplex in Friendship

You and your travel companions will be in an ideal Pgh spot when you stay at this Friendship neighborhood home. With 3 floors, you'll have lots of room to spread out or gather together. This beautifully updated 100-year-old home is a creative space, filled with art from Pgh artists, cheery textiles from around the world, and vintage decor scattered throughout. It’s a charming retreat for artists & writers, a cozy spot for families, or the perfect place for larger groups to share a getaway.

4.97 out of 5 average rating, 470 reviews

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

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.

A wooden staircase leads to the upper level, framed by polished handrails and original woodwork. A woven runner rug adds texture to the hardwood floor. A small console table stands against the wall, paired with a green potted plant. Light filters in through a nearby doorway.

5.0 out of 5 average rating, 113 reviews

Cheerful 3-bedroom home with on-street parking

Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

4.98 out of 5 average rating, 295 reviews

An outdoor deck is furnished with a seating arrangement that includes a woven sofa and armchairs. A low coffee table is centered on a colorful area rug featuring intricate patterns. Lush greenery surrounds the space, providing a natural backdrop.

Home in Export

Peaceful Export Escape

Enjoy this newly remodeled home with a spacious master bedroom and large deck. You'll be pleasantly surprised by the secluded and private feel of this space. It is perfect for a get away with family, friends, or all by yourself! Come relax, have fun, and explore all that the small town of Export has to offer. 25 minutes from Pittsburgh city center, 15 minutes from Monroeville, right off the Westmoreland Heritage Trail.

Popular amenities for Penn Hills house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.87 out of 5 average rating, 197 reviews

A large in-ground heated pool is showcased within a shaded outdoor area. Tall trees provide natural privacy, while bright blue waters reflect the clear sky. Lounge chairs are positioned along the edge of the pool, inviting relaxation in a serene setting.

Home in Monroeville

Mayberry Escape

4.81 out of 5 average rating, 105 reviews

A wooden dining table is positioned in the foreground, featuring a decorative orange fish centerpiece. The background reveals a modern kitchen with sleek granite countertops and a stylish backsplash, complemented by an overhead stainless steel range hood.

Home in Dormont

Renovated Cozy Duplex w/pool, Close to downtown

4.78 out of 5 average rating, 112 reviews

Home in Highland Park

Urban Pittsburgh Home w/ Pool

4.88 out of 5 average rating, 59 reviews

Relax in a 3bd & loft w/Pool in Plum PA

4.67 out of 5 average rating, 18 reviews

A beautiful cozy home away from home!

5.0 out of 5 average rating, 22 reviews

Home in South Side Flats

Rooftop Deck | Perfect for Entertaining | Upscale!

4.92 out of 5 average rating, 25 reviews

A private pool glistens in a vibrant blue, surrounded by a spacious deck. Lounge chairs with orange cushions are placed nearby, and a shaded seating area is visible under a large umbrella. Lush greenery and tiered wooden decking create a tranquil outdoor atmosphere.

Home in Brookline

Heated Pool Oasis • Free Parking • 5 min to PGH

4.57 out of 5 average rating, 63 reviews

A private pool is set within a spacious wooden deck, surrounded by lounge chairs and shaded areas. A vibrant beach ball floats on the water, and an umbrella offers shade nearby. Lush greenery is visible in the background, enhancing the outdoor space.

Home in New Kensington

Seasonal Pool Retreat | Fire Pit & Large Deck

Weekly house rentals

4.97 out of 5 average rating, 60 reviews

The Pitt Stop

A tree-lined pathway leads to a stone entrance, bordered by lush greenery. A decorative bench offers a resting spot, while the natural landscaping includes small shrubs and ground cover. The setting provides a calm entrance into the home, surrounded by a relaxed outdoor atmosphere.

4.87 out of 5 average rating, 84 reviews

The Stone House

A warm living area features a stone fireplace gently glowing with light. Comfortable seating arrangements include a sofa and an inviting window nook with colorful cushions. Natural light enters through multiple windows, highlighting the wooden beam ceilings and rich tones of the walls.

4.95 out of 5 average rating, 74 reviews

Cottage on a hill

A modern kitchen showcases light wood cabinetry paired with dark lower cabinets. Stainless steel appliances, including a refrigerator and microwave, are prominently featured. A gas cooktop is positioned on a spacious island, which offers ample counter space and is well-lit by an overhead light fixture.

4.91 out of 5 average rating, 47 reviews

Ranch Home: Cozy & Modern!

4.97 out of 5 average rating, 67 reviews

Family & Friendly Stay in Pittsburgh, PA.

A spacious bedroom features a large bed with neutral bedding and decorative pillows. Two bedside tables with lamps flank the bed, while a comfortable recliner and a small table create a cozy seating area. A large window allows natural light to fill the room, complemented by soft curtains.

4.93 out of 5 average rating, 92 reviews

HUGE Brand New Stylish Home ~ Parking~Theatre

A historic stone house showcases a mix of rustic and contemporary architecture. The building features a distinctive red roof accent and large windows, surrounded by manicured lawns and mature trees. A stone pathway leads to the entrance, enhancing the home's inviting appearance.

4.92 out of 5 average rating, 13 reviews

Charming Hillside Retreat

4.97 out of 5 average rating, 32 reviews

Home in Aspinwall

Aspinhaus

Private house rentals

4.65 out of 5 average rating, 48 reviews

A Home like yours in Verona, PA.

5.0 out of 5 average rating, 33 reviews

East End Pittsburgh 4 Bedroom Getaway

4.94 out of 5 average rating, 34 reviews

Home in Highland Park

Sergio's Gallery

5.0 out of 5 average rating, 12 reviews

Home in Monroeville

Gorgeous & Modern Home with HUGE Fenced-in Yard

4.74 out of 5 average rating, 27 reviews

NFL draft serene, Cozy beds "hill house" retreat

4.84 out of 5 average rating, 45 reviews

Peaceful Plum PA Home

A living area is presented with comfortable dark sofas adorned with plush throw pillows. A wooden coffee table occupies the center, while a decorative area rug lays beneath. Natural light filters through a nearby window, creating a cozy ambiance.

4.76 out of 5 average rating, 107 reviews

Verona Villa

The living room showcases a spacious sectional sofa arranged with decorative cushions, complemented by a soft throw blanket. Side tables with lamps add warmth, while framed artwork adorns the walls. A television is positioned in the corner, and natural light filters through sheer curtains.