Vacation rentals in Oakmont

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Top-rated vacation rentals in Oakmont

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Top guest favorite
A functional kitchen features grey cabinets complemented by wooden countertops. Open shelves display various glassware and kitchen essentials. A large sink with a dish drying rack is visible, alongside modern appliances, including a stainless steel refrigerator and coffee maker. Natural light enters through a window with blinds.
Home in North Side
4.93 out of 5 average rating, 207 reviews

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.

Superhost
The exterior of the house is shown, featuring a well-maintained brick facade. The covered porch leads to the front door, framed by two windows. Lush grass surrounds the walkway, emphasizing the welcoming entry. A hint of greenery is visible in the background.
Home in Monroeville
4.82 out of 5 average rating, 230 reviews

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

Superhost
The cabin exterior is seen surrounded by lush greenery. A small outdoor dining area features a table and four chairs under a yellow umbrella. A portion of the cabin façade is visible with wooden logs, while a stone fire pit can be seen in the foreground.
Cabin in Pittsburgh
4.9 out of 5 average rating, 167 reviews

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.

Superhost
The exterior of the historic log house is visible, showcasing its rustic charm with exposed logs. Vibrant foliage in shades of red and orange surrounds a furnished porch, while fallen leaves blanket the ground. The entrance is accessible via a small set of stairs.
Home in Verona
4.86 out of 5 average rating, 310 reviews

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.

Top guest favorite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 272 reviews

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.

Top guest favorite
Apartment in Pittsburgh
4.93 out of 5 average rating, 136 reviews

King Bed | 2 full bath | Deck! Hip Millvale!

Welcome to our spacious home! With 2 full bathrooms & 1 queen bedroom, our place is perfect for the traveling couple that loves privacy, or solo guests that want to spread out. Located in Millvale, our place is within walking distance to great breweries, shops & restaurants. Millvale has a massive amount of charm, with many of the same attributes of Lawrenceville at a lower price point. We're right over the bridge from Lawrenceville & a 5-minute drive to downtown & the North shore stadiums.

Guest favorite
The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.
Apartment in Pittsburgh
4.91 out of 5 average rating, 478 reviews

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.

Guest favorite
The interior space features a convertible sofa adorned with textured pillows, positioned opposite a boat control panel. Windows allow natural light to illuminate the area, offering views of the surrounding greenery. A small, round table complements the cozy living space.
Houseboat in Verona
4.95 out of 5 average rating, 100 reviews

Stationary Houseboat: The Oolikhanna

Come Glamp with us on our tiny 1972 Nautline houseboat located on the beautiful Allegheny River. We are in Verona, PA, a little river town about 10.7 miles upriver from Downtown Pittsburgh. Enjoy a complementary kayak, paddle board or canoe rental to enjoy the river. Create your own river adventure to Sycamore Island, or Plum Creek to explore or just take it easy and hang out on the houseboat and enjoy a dip in the Allegheny to cool off. Enjoy the sunset on the top deck.

Top guest favorite
The exterior of a brick building showcases a distinctive round turret topped with a slate roof. A blue front door, framed by an arched window, is highlighted by the warm tones of the surrounding brickwork. Symmetrical windows and decorative light fixtures add to the structure's charm.
Apartment in Pittsburgh
4.99 out of 5 average rating, 202 reviews

504 Bascom Ave Serene Luxury

Nestled in the middle of an adorable community of stone cottages, this historic structure built in 1938 was the first home John Mattys built in this neighborhood. He went on to build all the houses on Mattys (named after himself) and Oceanas Avenues (named for the sisters that commissioned and lived in this duplex). Re-imagined for contemporary lifestyles, 504 Bascom is your cozy cottage but with all the amenities you deserve. I look forward to hosting you!

Superhost
A bright living area is highlighted by a cozy sectional sofa, a coffee table, and a dining table for four. Natural light streams through three windows, illuminating the wood beams on the ceiling. A wall-mounted TV and a full kitchen are also visible in the space.
Apartment in Glenshaw
4.93 out of 5 average rating, 291 reviews

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

Top guest favorite
The living area includes a teal sofa paired with a brown armchair, positioned around a black coffee table. A decorative mirror with wooden accents is mounted on the wall, reflecting an inviting atmosphere. Two lamps offer soft lighting, and a patterned rug adds texture beneath.
Apartment in Pittsburgh
4.99 out of 5 average rating, 109 reviews

Pittsburgh Area 2 Bedroom Apt.

Comfortable, convenient, clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Downtown & Stadiums 10 mi. Universities, Medical Center & Carnegie Museums 8 mi. Monroeville Convention Center & Sri Venkateswara Temple 5mi, International A/P 27 mi. PENS Hockey Arena 9 mi. I-76 PA turnpike 8 mi. Kennywood Park 5 mi.

Top guest favorite
A cozy living area is showcased with a patterned area rug. A lamp provides soft lighting beside a comfortable armchair. A dining table with four chairs is visible in the background, featuring a vibrant piece of wall art. A modern refrigerator stands in the corner.
Guesthouse in Oakmont
4.98 out of 5 average rating, 113 reviews

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 & 5 minutes from PA Turnpike. Must be able to climb steps.

Popular amenities for Oakmont vacation rentals

Quick stats about vacation rentals in Oakmont

  • Total rentals

    70 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    830 reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Oakmont?

    Yes! Work meets play with ease at over 30 vacation rentals in Oakmont featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Oakmont?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with a kitchen, over 60 homes with wifi, over 50 homes with free parking, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do bed and breakfast rentals in Oakmont have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Oakmont. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakmont have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Oakmont. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Oakmont?

    Four-legged friends are welcome in Oakmont. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Oakmont have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Oakmont. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oakmont have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Oakmont. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Oakmont?

    Oakmont has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in bed and breakfast rentals in Oakmont?

    Experience the best of Oakmont with our bed and breakfast rentals, starting at about $400 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Where should I stay in Oakmont?

    Make yourself at home in Oakmont by choosing from our most frequently booked neighborhoods. We have over 370 vacation rentals in Dark Hollow Road, over 310 vacation rentals in Lower Oakmont, and over 370 vacation rentals in Upper Oakmont.

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