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Vacation rentals in Oakmont

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Top-rated vacation rentals in Oakmont

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Irwin

4.99 out of 5 average rating, 333 reviews

Accessible Private Suite - near PA Turnpike

Nicely decorated private suite with open floor plan designed for relaxation & comfort! Park in the wide driveway along the wall, a few steps away from the covered level entry door. Walk in, sit down & make yourself at home. Enjoy TV in the sitting area, sleeping in a comfy queen bed in the bedroom, free coffee in the kitchen, or taking a nice warm shower in the bath. Easy access to dining, shopping, Pgh & the Laurel Highlands via Rt 30 & PA Turnpike Exit 67. Hit ♥ to save & find us more easily!

Home in Verona

4.87 out of 5 average rating, 273 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.

Rental unit in Verona

4.94 out of 5 average rating, 105 reviews

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, paddle 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.

Guest suite in Highland Park

4.98 out of 5 average rating, 193 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.

Rental unit in Point Breeze

4.96 out of 5 average rating, 458 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Guest suite in Gibsonia

4.93 out of 5 average rating, 167 reviews

Cozy Comfortable Retreat #1

Beautiful basement guest suite with a gas fireplace, full bath, kitchen with cooktop stove, mini refrigerator and microwave/convection oven. Enjoy off street parking in a quiet friendly neighborhood with outdoor patio. Close to shopping, restaurants, North Park and Hartwood Acres. Downtown Pittsburgh is less than 13 miles away which allows for easy access to all the sporting events Steeler games, Pirate games and Penguin games. Located less than 2 miles from the PA turnpike exit.

Rental unit in Pittsburgh

4.91 out of 5 average rating, 395 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.

Cabin in Pittsburgh

4.93 out of 5 average rating, 143 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/night is $135.00 for 2 adults. Extra 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.

Rental unit in Glenshaw

4.95 out of 5 average rating, 230 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

Guest suite in Bloomfield

4.98 out of 5 average rating, 189 reviews

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

Townhouse in Pittsburgh

4.92 out of 5 average rating, 145 reviews

Family friendly *garage *10 min downtown

Nestled in a quiet neighborhood, our home is the perfect haven for families looking to explore the vibrant city of Pittsburgh. With ample space for everyone to spread out and relax, our home offers a comfortable and inviting atmosphere. We offer premium amenities, including whole bean coffee, tea selection, soft towels, toiletries, and in-unit laundry (w/d) with laundry supplies provided.

Home in New Kensington

4.99 out of 5 average rating, 125 reviews

Mid-Century Burrell Bungalow

Located only 30 minutes from the beautiful city of Pittsburgh, this newly renovated home is nestled in a quiet, dog & family friendly rural neighborhood. While the home is playground-adjacent & located just up the hill from the rails-to-trails along the Allegheny River, the backyard is fenced in & perfectly suited for families & furry friends alike.

Vacation rentals for every style

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Popular amenities for Oakmont vacation rentals

Free parking on premises

Air conditioning

Stay near Oakmont's top sights

Oakmont Bakery25 locals recommend

Carnivores11 locals recommend

Zone 286 locals recommend

Oakmont Country Club6 locals recommend

Hoffstot's Cafe Monaco6 locals recommend

The Lot at Edgewater6 locals recommend

Other great vacation rentals in Oakmont

Home in Verona

4.88 out of 5 average rating, 69 reviews

Neighborhood Charmer

Rental unit in Shadyside

4.98 out of 5 average rating, 48 reviews

Shadyside/Central @4 Stylish&Central Studio w/Prkg

Home in Munhall

4.98 out of 5 average rating, 64 reviews

Private House with Stone Patio and Sun Room

Rental unit in Export

5 out of 5 average rating, 17 reviews

Trailside Comforts

Home in Pittsburgh

4.94 out of 5 average rating, 36 reviews

Country Club Cottage - 20 minutes from downtown

Guest suite in Sarver

5 out of 5 average rating, 40 reviews

Open concept design studio

Rental unit in Aspinwall

4.98 out of 5 average rating, 57 reviews

Aspinwall 1 bedroom Apartment

Rental unit in Pittsburgh

4.97 out of 5 average rating, 39 reviews

Pittsburgh Area 2 Bedroom Apt.

Quick stats about vacation rentals in Oakmont

Total rentals
40 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
640 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 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 10 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 20 homes with free parking, over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Oakmont have wifi?
Absolutely! We offer over 20 house 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 20 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 10 vacation rentals for guests traveling with pets.
Do house rentals in Oakmont have free parking?
Absolutely! We offer over 20 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 20 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 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oakmont?
Experience the best of Oakmont with our house rentals, starting at about $60 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 290 vacation rentals in Upper Oakmont, over 250 vacation rentals in Lower Oakmont, and over 290 vacation rentals in Dark Hollow Road.

Destinations to explore