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Holiday rentals in Oakmont

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Top-rated holiday rentals in Oakmont

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

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Home in Monroeville

4.81 out of 5 average rating, 185 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

29 Dec – 5 Jan

$189 SGD per night

Home in Verona

4.87 out of 5 average rating, 247 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.

29 Apr – 6 May

$132 SGD per night

Guest favourite

Guest suite in Pittsburgh

4.97 out of 5 average rating, 139 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.

5–10 Sep

$117 SGD per night

Guest favourite

Flat in Pittsburgh

4.95 out of 5 average rating, 387 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!

7–14 Jan

$112 SGD per night

Guest favourite

Guest suite in Gibsonia

4.94 out of 5 average rating, 140 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.

28 Jul – 4 Aug

$131 SGD per night

Guest favourite

Flat in Pittsburgh

4.91 out of 5 average rating, 327 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.

17–24 Feb

$129 SGD per night

Guest favourite

Guest house in Oakmont

4.97 out of 5 average rating, 75 reviews

Cozy Carriage House in Oakmont, PA

Newly renovated detached Carriage House with off-street parking. Sleeps 4 people comfortably with master bedroom on the main floor. Ideal for golfers at the famous Oakmont Country Club or a few days stay in beautiful Oakmont, PA. 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. May not be suitable for small children. Must be able to climb steps.

29 Sep – 6 Oct

$258 SGD per night

Guest favourite

Cabin in Pittsburgh

4.92 out of 5 average rating, 126 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.

29 Jan – 5 Feb

$210 SGD per night

Guest favourite

Flat in Glenshaw

4.95 out of 5 average rating, 195 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

11–18 Sep

$106 SGD per night

Guest favourite

Home in Irwin

5.0 out of 5 average rating, 108 reviews

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 .

19–26 Nov

$147 SGD per night

Guest favourite

Townhouse in Pittsburgh

4.92 out of 5 average rating, 120 reviews

Family friendly *garage parking *10 min DT Pitt

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.

9–16 Mar

$216 SGD per night

Guest favourite

Guest suite in Pittsburgh

4.94 out of 5 average rating, 198 reviews

Sweet Mid-Century Modern Suite/Attached Garage

Half-above ground basement studio with secured garage parking (keyless entry) in quiet, peaceful, "Mr. Rogers" neighborhood. Mid-century comfort with modern amenities and eclectic furnishings. Private bath and kitchenette. New queen-size bed, new shower, and new three-quarter sofa bed. Comfortable for single, couple, and 1-2 children. Ground level patio. No stairs or steps.

13–20 Jul

$140 SGD per night

Holiday rentals for every style

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Popular amenities for Oakmont holiday rentals

Free parking on premises

Air conditioning

Stay near Oakmont's top sights

Oakmont Bakery25 locals recommend

The Lot at Edgewater6 locals recommend

Carnivores11 locals recommend

The Pub at 3335 locals recommend

Hoffstot's Cafe Monaco6 locals recommend

The Oaks Theater4 locals recommend

Other great holiday rentals in Oakmont

Guest favourite

Bungalow in Oakmont

4.98 out of 5 average rating, 63 reviews

Oakmont Home with Hot Tub

1–6 Aug

$274 SGD per night

Flat in Springdale

4.79 out of 5 average rating, 42 reviews

2br gem in cute small town.

12–19 Sep

$134 SGD per night

Guest favourite

Flat in Verona

4.96 out of 5 average rating, 90 reviews

The Sycamore BnB @ 10.7 Marina

16–23 Jan

$272 SGD per night

Guest favourite

Home in Monroeville

5.0 out of 5 average rating, 12 reviews

Monroeville 2 bedroom 2 queen size beds

10–17 Jul

$112 SGD per night

Guest favourite

Flat in Aspinwall

4.97 out of 5 average rating, 35 reviews

Aspinwall 1 bedroom Apartment

30 Nov – 7 Dec

$163 SGD per night

Guest favourite

Home in New Kensington

4.98 out of 5 average rating, 65 reviews

Mid-Century Burrell Bungalow

28 Dec – 4 Jan

$266 SGD per night

Home in Brackenridge

4.8 out of 5 average rating, 15 reviews

Cozy two bedroom

30 Sep – 7 Oct

$142 SGD per night

Guest favourite

Flat in Pittsburgh

5.0 out of 5 average rating, 7 reviews

Upscale King Suite by WholeFoods

11–18 Dec

$143 SGD per night

Quick stats about holiday rentals in Oakmont

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
450 reviews
Nightly prices starting at
$41 SGD before taxes and fees

Destinations to explore