Holiday rentals in Pittsburgh

Cliffside Luxury with Spectacular City Views

Amazing views, rooftop patio w/fire pit, contemporary design and furnishings are just the beginning for your amazing stay at our cliffside paradise. This architecturally stunning home offers a fully equipped kitchen, two decks to dine and relax on. Beyond its walls, you can visit the nearby Station Square shops and restaurants, 2 Inclines, Pittsburgh Zoo and PPG Aquarium, Warhol Museum, the Rivers Casino, or watch the Penguins at PPG Arena, Steelers at Heinz Field, and the Pirates at PNC Park!

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!

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.

Chic Loft Style HighEnd King Suite~ 2Parking Spots

Brand New Loft Style Apartment with 17ft. ceilings, huge windows, and 2 dedicated OffStreet Parking Spaces! Brand new KING Suite! 1 block to West Penn, short walk to UPMC! On site parking makes the short drive to Shadyside, CMU, Pitt and the Strip District/Downtown a breeze! The building was gutted and remodeled, everything is brand new! Fully stocked for long and short term stays! Steps to dozens of restaurants, shops, coffee shops, and grocery stores. Make your reservation today!

Immaculate Double King Suite w/ Rooftop Terrace

Enjoy our immaculate 2 BR Penthouse suite on Butler Street, right in the heart of Lawrenceville. This is a brand new construction building in 2025. Just steps away from several local shops, cafes, and dining options in one of Pittsburgh’s most vibrant neighborhoods. ⭐2 King Beds (memory foam mattresses) ⭐1 Queen Sleeper sofa + 1 Queen Murphy Bed + Pack N Play ⭐Rooftop Deck w/ City view ⭐Free in-unit washer/dryer ⭐Free off-street parking ⭐Desk with speedy wifi ⭐24/7 guest support

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.

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!

Modern Condo with Skyline View & Parking

Escape to our modern Pittsburgh retreat in sought-after Lawrenceville! This new condo comfortably fits 4, featuring a plush King bed & Queen sleeper sofa. Enjoy stunning city skyline views from the Juliette balcony. Perfect for couples or small groups, you're just a short walk from top restaurants & shops. Includes a dedicated workspace, gourmet kitchen, and free parking. A stylish and convenient base to explore the best of Pittsburgh!

Exposed Beams, Modern Vintage War Streets Charmer!

✨ Discover the charm of Pittsburgh’s historic Mexican War Streets! This stylish 2BD/1BA home combines exposed brick, rich wood tones, and modern comforts for a warm, inviting stay. ☕ Enjoy locally roasted coffee, lounge on the cozy sectional, or catch up on work before heading out. With PNC Park, Acrisure Stadium, the Warhol Museum, and top dining just minutes away, you’ll love exploring this highly walkable neighborhood! 🚶‍♂️🏙️

Modern Victorian Apartment - Quiet but walkable!

This 3rd floor apartment is located in the heart of the Northside in Mexican War streets. It’s freshly renovated with a massive kitchen and living room/dining room. A block away from Commonplace Coffee and under 15 minute walk to just about everything, including Pirates, Steelers, Aviary, children’s museum, Federal Street, Western Ave and more! We love this neighborhood and you’ll love it too!

Penthouse|PRIME PARKING|Beside PPG|Private Rooftop

🌆⭐Stay in the BEST location in Pittsburgh, right on 5th Ave beside PPG Paints Arena (Penguins hockey + concerts literally steps away). Enjoy a luxury designer penthouse with a huge corner rooftop patio and sleek garage-style doors for epic indoor/outdoor vibes. Walk to top dining, nightlife, and downtown attractions. Perfect for groups or business travel! 🏙️🏒🥂

Bright 1BR Downtown Pittsburgh Near DLCC

This bright 1-bedroom apartment offers modern furnishings, upscale appliances, and abundant natural light. Located steps from the David L. Lawrence Convention Center, it’s perfect for business travelers and event-goers. Walk to Market Square, PNC Park, and the Cultural District while enjoying comfort, convenience, and Pittsburgh’s vibrant downtown lifestyle.