
House holiday rentals in Oakmont
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Top-rated house rentals in Oakmont
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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.

Mayberry Escape
Discover the charm of this inviting 3-bed, 3.5-bath Monroeville home! Immerse yourself in luxury with a heated pool (seasonal), rejuvenating infrared sauna, expansive decks, a private backyard, a fully equipped kitchen, a finished basement, and a delightful fire pit overlooking the pool. Experience comfort and style with off-street parking included. Enquire now to make this your own sanctuary! ***If you enjoy this space, the owners are amenable to selling. Please contact for more information***

Pittsburgh Hideaway - Pets - Private
-Discounts on weekly and monthly stays - Put in dates for prices. -1 bedroom house with 1 bath and everything you need for a comfortable stay. -House is tucked away, but also close to the highway and turnpike. -Walking distance to UPMC East, 6 minutes to Forbes Hospital, and min from major shopping/restaurants. -Pet friendly with a large yard (no fence). -Dog park only 7 minutes away - Monroeville Dog Park. Boyce Park and Penn Hills (fenced dog parks) 15 min away -TV- Amazon Stick to login

Private Hot Tub | King Beds 1 Block from Butler St
Great value at this spotless centrally located private home with all the bells and whistles! *Air hockey table *Convertible table that turns into a Ping Pong Table or Pool Table *Outdoor deck with 2 person HOT TUB! Newly renovated & professionally decorated 3 Bedroom with 4 Comfy Beds. *Two individual KING suites w/TVs. *Third Floor Bedroom with two double beds & TV. Short walk to popular Butler Street bars & restaurants. Quick Uber ride (10 minutes) to downtown & all sports venues!

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.

Gorgeous Modernized Cabin + Hot Tub + Pool Table
Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

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.

Entire home near Kennywood without extra fees.
Bring everyone along for the trip, including Fido! Our home is a cozy, yet spacious Cape Cod southeast of downtown Pittsburgh. The backyard faces a beautiful and peaceful meadow. The yard is fenced in and has a small garden filled with herbs and tomatoes during the summer. Our home has all of the amenities to make your stay enjoyable and easy. We keep our home clean, organized and stocked with essentials. The beds, pillows and sheets are new and comfortable. Parking is plentiful and easy!

Seneca Place: A historic home in Mount Lebanon.
Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

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.

Our cozy contemporary home near PA turnpike
Enjoy this peaceful, private residence conveniently located <5 miles from PA turnpike exit 67 with quick access to many restaurants and retail establishments. This is a nicely appointed and recently renovated ranch home in a residential neighborhood with a peaceful outdoor space. There is an open concept living room, dining area and new modern kitchen with stainless steel appliances. The bedrooms have comfortable beds with down comforters .

6min to Pittsburgh Zoo,Pet Friendly,Near Butler St
Located in Upper Lawrenceville, Pittsburgh, PA, this spacious 4-bedroom, 2.5-bathroom property stands out in the neighborhood. With an inviting open layout, a chef's kitchen, and a luxurious master suite, it combines modern comfort with timeless charm. The prime location offers easy access to trendy shops and eateries. Enjoy this unique Upper Lawrenceville property's perfect blend of space, style, and convenience.
Popular amenities for Oakmont house rentals
House rentals with a pool

Country Retreat: Indoor Pool/Pickle Ball/Sleeps 12

Convenient townhome

Renovated Cozy Duplex w/pool, Close to downtown

Cheerful 4BR Chalet with Seasonal Pool, Hot Tub

Spacious House w/ Pool @Wexford

PIT Staycation Retreat with Pool House!

3BR Home w/ Pool, Deck, Scenery, near Pittsburgh

Eastside Vibes ~ Roomy. Peaceful. Charming.
Weekly house rentals

*z 2231 1BR Southside *Sloped* Home Close to Pgh

Aspinhaus

Contemporary Comfort Near Pittsburgh Pa - 13mi

Urban Spa Retreat· Sauna · Gym · Smart Beds · Pool

Comfortable & Charming Cottage

3BR/2BA Hidden Gem on the Allegheny River

Yew Arbor Cottage

Near Hospitals + Great Food, w/ Off-Street Parking
Private house rentals

Renovated 4-bedroom Farmhouse

Grand on Grant

Delightfully Cozy & Well Provisioned Home

Historic Luxury in Highland Park

Rooftop Deck Sunsets, Fire Pit Nights, Walk to Fun

Pet friendly/safe by Oakmont, Veltres + Pittsburgh

Quiet/safe 2BR House in Churchill with King Bed

2 beds/1.5 bath Hygge-Hus, Minute to Cafes & Shops
Quick stats about house rentals in Oakmont
Total holiday rentals
Explore 50 holiday rentals in Oakmont
Nightly prices starting at
Oakmont holiday rentals start at $108 AUD per night before taxes and fees
Verified guest reviews
Over 450 verified reviews to help you choose
Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
50 of Oakmont holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oakmont rentals
4.9 Average rating
Oakmont stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a washing machine and dryer Oakmont
- Rentals with outdoor seating Oakmont
- Pet-friendly rentals Oakmont
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- Rentals with a patio Oakmont
- Rentals with a fire pit Oakmont
- Family-friendly rentals Oakmont
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- House rentals Allegheny County
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- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Ohiopyle State Park
- Oakmont Country Club
- Raccoon Creek State Park
- Kennywood
- Yellow Creek State Park
- National Aviary
- Phipps Conservatory and Botanical Gardens
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Point State Park
- Narcisi Winery
- Schenley Park
- Senator John Heinz History Center
- Bella Terra Vineyards
- Children's Museum of Pittsburgh
- Cathedral of Learning
- Laurel Mountain Ski Resort