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Family-friendly holiday rentals in Oakmont

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oakmont

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Home in Monroeville

4.84 out of 5 average rating, 141 reviews

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***

21–28 Nov

$495 SGD per night

Guest favourite

Home in Pittsburgh

4.92 out of 5 average rating, 264 reviews

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

16–23 Sep

$180 SGD per night

Guest favourite

Flat in Pittsburgh

4.95 out of 5 average rating, 241 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

*PLENTY OF FREE STREET PARKING* 1 BDRM apt in the up and coming town of Bellevue, just a 10 min drive to downtown and the stadiums. This is a 2nd floor unit in my 100+ year old four-square home. It has a private entrance with a keypad for Airbnb guests, there are 2 other units in the building. Its in walking distance to public transit, shops, restaurants, places of worship, banks, and a grocery store. Pet friendly ($50 fee) just add your pet under pets in the guest section when booking.

28 Mar – 4 Apr

$154 SGD per night

Guest favourite

Flat in Pittsburgh

4.95 out of 5 average rating, 391 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!

3–10 Sep

$131 SGD per night

Guest favourite

Flat in Pittsburgh

4.97 out of 5 average rating, 310 reviews

Apartment: Home Sweet Home

Enjoy yourself in a bright, one floor living space, with a separate bedroom, (Queen Size bed), bathroom (shower) and living room. Sleeps 4 comfortably. Queen size sofa bed in living room sleeps 2. Private entrance with lock box and private off street parking. 6 miles from Downtown Pittsburgh sports and activities. Close to shopping, pizza and restaurants. Uber available. Enjoy sweet bread or muffins with coffee or tea to begin your stay! We are happy to meet your needs!

24–31 Oct

$190 SGD per night

Guest favourite

Guest suite in Pittsburgh

4.84 out of 5 average rating, 206 reviews

Entire private floor (giant Jacuzzi with shower!)

Welcome! In addition to having numerous "sparkling clean" reviews, I am committed to helping Airbnb guests stay safe by cleaning and disinfecting frequently touched surfaces. This is a finished basement in my house with its own entry way. Being below ground helps keep things cool in the summer. Off-street parking pad available in back of house (look for small Amish shed). Safe, quiet, and family-oriented neighborhood minutes from the Zoo, Highland Park, and downtown!

9–16 Jul

$153 SGD per night

Guest favourite

Flat in Pittsburgh

4.92 out of 5 average rating, 410 reviews

Historic Charmer | Spacious | Off Street Parking

2200 sf, beautiful two-bedroom apartment located on the second floor of an 1887 Queen Anne Victorian Home. Private staircase, entrance, and deck with amazing views of the Ohio River and Emsworth Lock and Dam. Only 6 miles from Heinz Field and PNC Park and 15 miles from Pittsburgh International Airport. One block from public transportation. The house is on a large lot with flower and vegetable gardens, fruit trees, and an oak tree that is one of the largest in the area.

21–28 Aug

$154 SGD per night

Guest favourite

Cabin in Pittsburgh

4.92 out of 5 average rating, 127 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.

26 Apr – 3 May

$214 SGD per night

Guest favourite

Home in Pittsburgh

4.97 out of 5 average rating, 154 reviews

Luxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks

Pittsburgh's premier, top of the line Airbnb! No expense was spared outfitting our 4 bedroom, 2.5 bath home! Amenities galore both indoors & out with 3 large outdoor spaces, fire pit, and garage parking. Every high end detail has been meticulously selected and designed. Take advantage of all the city of Pittsburgh has to offer in the lap of luxury with your own centrally located private residence on the North Side, complete with a Peloton for the healthy-minded!

24–31 Mar

$755 SGD per night

Guest favourite

Flat in Pittsburgh

4.97 out of 5 average rating, 378 reviews

Modern Love Apartment - Heart of Lawrenceville!

This private apartment (with it's own entrance) is on the lowest level of our house. It is walking distance to the best of lively Lawrenceville. It is centrally located in Pittsburgh and close to downtown, the universities and the stadiums. We are right off of Butler Street which is where the shops and restaurants are located. There is free street parking directly in front of the house. Dozens of restaurants and shops are just a short walk away.

2–9 Aug

$180 SGD per night

Guest favourite

Home in Pittsburgh

4.88 out of 5 average rating, 422 reviews

PRIVATE MINI STUDIO (D2)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

21–28 Sep

$129 SGD per night

Guest favourite

Guest suite in Pittsburgh

4.98 out of 5 average rating, 233 reviews

Large victorian 3rd flr apt in walkable eastend

An entire third floor apartment of a historic Colonial Revival house. Two bedrooms, each with a firm queen memory foam bed, one bathroom with claw foot tub/shower, huge living room with seating area and desk, and a fully equipped kitchen with washer and dryer. Walk up to third floor. A queen air mattress bed or pack n' play can be added to any one of the bedrooms or the living room, just let us know.

3–10 Oct

$207 SGD per night

Holiday rentals for every style

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Popular amenities for Oakmont family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Home in Pittsburgh

4.91 out of 5 average rating, 143 reviews

My Favorite Sunny Bunny Eco Luxe Stay (Blue)

22–29 Oct

$719 SGD per night

Guest favourite

Home in Pittsburgh

5.0 out of 5 average rating, 10 reviews

Luxe Shadyside Spa + Parking + 5 Beds + Zen Garden

3–10 Apr

$542 SGD per night

Guest favourite

Bungalow in Oakmont

4.98 out of 5 average rating, 64 reviews

Oakmont Home with Hot Tub

20–27 Oct

$279 SGD per night

Guest favourite

Home in Pittsburgh

4.88 out of 5 average rating, 73 reviews

Sunny Bunny Eco Luxe Art & Wellness House (Green)

25 Feb – 4 Mar

$833 SGD per night

Guest favourite

Bungalow in Oakmont

4.96 out of 5 average rating, 53 reviews

Oakmont home with private hot tub

20–27 Oct

$374 SGD per night

Guest favourite

Home in Pittsburgh

5.0 out of 5 average rating, 18 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

4–11 Nov

$979 SGD per night

Family- and pet-friendly home rentals

Flat in Pittsburgh

4.87 out of 5 average rating, 281 reviews

Cozy + Modern apartment near the city!

11–18 Jul

$128 SGD per night

Guest favourite

Tiny home in Mount Pleasant

4.97 out of 5 average rating, 259 reviews

Tiny House - Big Farm Adventure near Pittsburgh

29 Nov – 6 Dec

$172 SGD per night

Guest favourite

Home in Butler

4.98 out of 5 average rating, 177 reviews

Meadow Rock Farm-6BR/4Bath, Sleeps 20

14–21 Nov

$1,160 SGD per night

Guest favourite

Townhouse in Pittsburgh

4.93 out of 5 average rating, 320 reviews

Charming Home • Vibrant Neighborhood

5–12 Nov

$329 SGD per night

Guest favourite

Home in Pittsburgh

5.0 out of 5 average rating, 209 reviews

High-End South Side 4 Bedroom House, sleeps 15!

28 Aug – 4 Sep

$834 SGD per night

Guest favourite

Townhouse in Pittsburgh

4.88 out of 5 average rating, 99 reviews

Modern/Industrial Townhouse in Lawrenceville

20–27 Sep

$127 SGD per night

Guest favourite

Home in Sarver

4.93 out of 5 average rating, 60 reviews

Stoney Creek

21–28 Feb

$366 SGD per night

Home in Pittsburgh

4.91 out of 5 average rating, 11 reviews

House 3bed Free Parking Walk to Bars & Shops

19–26 Sep

$301 SGD per night

Family-friendly home rentals with wifi

Flat in Pittsburgh

4.81 out of 5 average rating, 270 reviews

Apt 7 Bloomfield/Lawrenceville private mini studio

6–13 Jul

$152 SGD per night

Guest favourite

Home in Munhall

4.8 out of 5 average rating, 218 reviews

Beautiful 3 Bedroom Home Cozy Front and Back Porch

31 May – 7 Jun

$174 SGD per night

Guest favourite

Home in Pittsburgh

4.98 out of 5 average rating, 156 reviews

Spacious, attractive apartment in residential home

20–27 Aug

$141 SGD per night

Flat in Pittsburgh

4.93 out of 5 average rating, 331 reviews

Delightful Artsy & Private Apartment, East End PGH

24 Jun – 1 Jul

$161 SGD per night

Guest favourite

Home in Pittsburgh

4.92 out of 5 average rating, 228 reviews

Cozy home in "Little Italy"

18–25 Jul

$221 SGD per night

Guest favourite

Flat in Coraopolis

4.97 out of 5 average rating, 179 reviews

Moon Professional Living Suite B

7–14 Jun

$102 SGD per night

Guest favourite

Home in Monaca

4.99 out of 5 average rating, 181 reviews

Serenity Now!

13–20 Dec

$250 SGD per night

Guest favourite

Home in Pittsburgh

4.98 out of 5 average rating, 180 reviews

PBR - Pittsburgh Bloomfield Rowhouse

26 Oct – 2 Nov

$237 SGD per night

Quick stats about holiday rentals that are family-friendly in Oakmont

Total rentals
20 properties
Local attractions
Oakmont Bakery, The Lot at Edgewater and Carnivores
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
280 reviews
Nightly prices starting at
$95 SGD before taxes and fees

Destinations to explore