Family-friendly holiday rentals in Pittsburgh

Luxury Mountainside with Spectacular Views

Furnished by West Elm and RH (Restoration Hardware) to deliver a one of a kind luxury experience. Amazing views, two huge patios, one with a concrete propane fire-pit, modern design and furnishings are just the beginning of your amazing stay at our cliffside paradise. This architecturally stunning smart home offers a fully equipped chef's kitchen, and the highest end furnishings to make this the perfect getaway. Have a Tesla? Bring your charger to plug into our 220V outlet at the driveway!

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!

Stunning King Suite |Unbeatable Downtown Location!

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!

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet

Stylish and freshly renovated 1 BR/ 1 bath apartment perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! Fully equipped for an extended stay, weekend getaway, or just a place to crash for the night. ⭐️Super comfy queen memory foam mattress 🌟24/7 Guest support ⭐️Free off-street parking! 🌟Fully stocked & equipped kitchen ⭐️Queen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ⭐️Laundry (Free and in-unit)

King Bed | Amazing Location | Stunning Design

✨Modern Nordic charm in the heart of Lawrenceville!✨ Just two blocks from Butler Street, you’ll be surrounded by Pittsburgh’s best bars, restaurants, coffee shops, & patios. This art-filled 2BR home combines thoughtful design with high-speed internet, two 55” 4K TVs, and a cozy loft office. Cook in the fully stocked kitchen, stream your favorites, or unwind in a space that’s as functional as it is stylish. Recently remodeled with comfort in mind—it’s the perfect home base for work or play!

Highly rated, 2bd/1.5 bath home/backyard/parking

Welcome to La Casita Millvale, a newly renovated 2 br/1.5 bath (sleeps 6) home in the heart of trendy Millvale/Lawrenceville and close to all Pittsburgh has to offer. Enjoy our expertly designed space including fully equipped kitchen with quartz countertops and stainless steel appliances, well-apportioned rooms with luxurious queen mattresses, and a third floor entertainment room and work space. Sip your morning coffee on the front or back porch and relax in the private backyard.

Urban serenity, privacy in charming carriage house

Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

Shadyside/Pittsburgh, Modern & Unique 1BD w/Prkng

Unique and family oriented modern 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 bedroom & Dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!