Family-friendly holiday rentals in Oakmont

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.

Kitchen · Family · Cleanliness

The Sycamore BnB @ 10.7 Marina

Stay above 10.7 Marina on the Allegheny River, in Verona, PA, a little river town about 10.7 miles upriver from Downtown Pittsburgh. Enjoy a complementary kayak frompad board or canoe rental to enjoy a river adventure or dip in the Allegheny to cool off. Create your own river adventure to Sycamore Island, or Plum Creek to explore. You can also take it easy and hang out on the deck with panoramic views of this “lake like view” and enjoy the many sunsets. Eat, drink and shop many local spots.

Indoor spaces · Kitchen · Getting around

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Indoor spaces · Family · Sleep quality

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost you see per night is for 2 guests. Added adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day. I will collect that later.

Family · Indoor spaces · Pets

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.

Kitchen · Indoor spaces · Barbecue

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!

Indoor spaces · Kitchen · Solo travel

Luxurious 2Bed by Whole Foods

Brand new construction, high end spacious 2 bedroom with designated off street parking! Double King Suites and Full Size pullout bed offer enough room for the whole family Enjoy the convenience of being across the street from WholeFoods & steps to dozens of restaurants & shops, short Walk to UPMC Shadyside, West Penn, & Children's hospitals, close CMU & Pitt! Enjoy dozens of restaurants shops and coffee shops just a walk away! Fully stocked for both long and short term stays!

Family · Indoor spaces · Getting around

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

Indoor spaces · Family · Quiet

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

Family · Kitchen · Layout

2br gem in cute small town.

The whole group will enjoy easy access to everything from this centrally located place. Grab a book about Pittsburgh from the coffee table and find some fun things to do or have game night with the selection of board games. Sip a beverage on the back porch or make s’mores at the fire pit. Easy access to Pittsburgh, hop on 28 and be there in no time, or ride one of the busses that stop outside the door. 13 miles to PNC Park 14 miles to Acrisure Stadium

Family · Kitchen · Location

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

Indoor spaces · Family · Pets

Cozy Carriage House in Oakmont, PA

Freshly updated detached Carriage House with off-street parking. Sleeps 4 adults comfortably. Minutes from Oakmont Country Club. Walkable to Allegheny River Boulevard shops and Oakmont Bakery. Living room and Main Bedroom equipped with Smart TVs. Standard cable + HBO. Private patio area with seating. 20 minutes from Downtown Pittsburgh, Acrisure Stadium, Rivers Casino, and PNC Park. 5 minutes from PA Turnpike. Must be able to climb steps.

Indoor spaces · Kitchen · TV