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 · Bathroom

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

Location · Value · Hospitality

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.

Value · Location · Outdoor spaces

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

This charming historical home is close to everything! You can be downtown within 5 minutes. You'll be minutes from the stadiums, museums, and the casino! Pamper yourself. Relax in the hot tub while listening to the sounds of the waterfall over the pond. Watch the colorful Koi splash and play. The meticulously landscaped grounds have countless surprises and beauty in every season. You will enjoy every comfort in this luxurious three-bedroom and 2.5 baths. There's even a shower for your furbaby!

Location · Value · Hospitality

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.

Location · Family · Breakfast

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.

Family · Value · Indoor spaces

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.

Family · Value · Checkout

Modern & Spacious 4BD House in Pittsburgh w/Prkg

Family Oriented and Spacious house with a convenient location and minutes to Pittsburgh. Enjoy the beautiful mornings with incredible sunrises and tranquille dawns with the proximity to shopping, bars & restaurants. This house features 4 bedrooms, 3 baths, Large Dining and living areas, cozy Backyard. Stylishly setup, the house features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families only and this is NOT a party place.

Value · Location · View

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!

Location · Family · Outdoor spaces

Huge 6 BDRM min to Downtown & Stadiums w/ parking

Gather with friends and family in our renovated Pittsburgh home, designed for comfort and fun! ✅ 6 Large Bedrooms & 3 Full Baths – Includes a soaking tub ✅ Easy Parking – Two-car driveway + plenty of free street parking ✅ Stocked Kitchen – Fully equipped with essentials ✅ Spacious Living Areas – Two living rooms for lounging ✅ Entertainment – Projector & sound system for movie nights ✅ Family & Pet-Friendly – Room for everyone ✅ Cozy Fireplace – Available Nov.–Feb. Everyone will enjoy it!

Value · Family · Long stay

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.

Family · Location · Checkout

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 · Value · Checkout