House holiday rentals in Penn Hills

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!

Value · Family · Cleanliness

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

Family · Value · Walkability

Serene Secluded Hilltop Hideaway. Hot Tub Fire Pit

A peaceful escape close to the city. Nestled in a private wooded setting, this 4BR home is just 15 minutes from downtown Pittsburgh. Relax on a wrap-around balcony, unwind in the hot tub, or gather for conversation around the fire pit under the trees. With space for families, pets, and friends, plus trails just steps away, it’s a perfect blend of natural privacy and city convenience. The inside offers a refined treehouse vibe - with warm, modern interiors surrounded by serene woodland views.

Family · Location · Outdoor spaces

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.

Value · Family · Heating

Top Guest favourite

Guest favourite

Scenic Haven: Downtown 3BR/2BA w/Parking + Patio

Welcome to our charming 3Bedroom (5 Beds), 2Bath home! Ideal sanctuary for families or groups of up to 8 guests. Nestled above the heart of the city, this delightful Mt Washington property promises scenic views and a memorable stay with a blend of warmth and modern comfort. Cozy ambiance surrounds you, and the off street driveway parking makes things a breeze. Peaceful family oriented neighborhood providing the perfect location to unwind and relax after a day of exploration and fun in the city.

Value · Family · TV

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.

Value · Family · Long stay

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!

Value · Location · Outdoor spaces

Stylish & Bright 3Bd Home, Amazing Deck, Game Room

Stylish and family oriented house 8 mins from Pittsburgh, NHL and NFL games. Enjoy the beautiful mornings with incredible sunrises and tranquille dawns with the proximity to shopping, bars & restaurants in Lawrenceville. This house features 3 bedrooms, Lounge/Dining areas, Backyard, Game room, Hockey Arena right in the house. Stylishly setup, our home has high speed internet and Security system for safety of our guests. This place is suitable for families only and this is NOT a party place.

Family · Location · Pool

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.

Family · Location · Hospitality

Top Guest favourite

Guest favourite

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.

Location · Family · Outdoor spaces

Top Guest favourite

Guest favourite

The Pitt Stop

Relax and enjoy in this comfortable peaceful place. It is situated in a convenient location close to the City of Pittsburgh, approximately 20 minutes from downtown and the stadiums as well as many city attractions such as the Pittsburgh Zoo! If you are in town for other reasons we have great restraunts, bars and brewerys and the famous oakmont bakery all within 5-7 minutes away. We have added 2 complementary guest passes to Anytime Fitness only a 5 minute drive from the Pitt stop.

Family · Value · Outdoor spaces

Pet Friendly Pittsburgh Home Near Zoo, Sleeps 12

Spacious 4BR pet-friendly home in Upper Lawrenceville, Pittsburgh. Minutes from Pittsburgh Zoo, Strip District, Children's Hospital, and Butler Street dining. Easy access to PNC Park, Acrisure Stadium, PPG Paints Arena, and Pitt/CMU. Open layout with chef's kitchen, luxurious master suite, and modern finishes. Ideal for families, medical stays at UPMC, game-day trips, graduations, and group travel. Free parking and walkable to Lawrenceville's best restaurants and shops.

Family · Location · Amenities