90+ Private Villas and Holiday Rentals in Oakmont |
Oakmont Holiday Rentals
Cabin
- Pennsylvania
- ·
- Bairdford
- 5.42 mi to center
10.0Exceptional
(109 Reviews)
2 Bedrooms
1 Bath
6 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $154/Night
7 Nights - US $1,077
House
- Pittsburgh
- ·
- Verona
- 0.90 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
2 Baths
11 Guests
2195.84 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Air Conditioner
US $188/Night
7 Nights - US $1,316
Bed & Breakfast
- Pittsburgh
- ·
- Plum
- 3.23 mi to center
10.0Exceptional
(37 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Parking
US $415/Night
7 Nights - US $2,906
Apartment
- Pittsburgh
- ·
- Verona
- 0.97 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,282
Apartment
- Pittsburgh
- ·
- Harmarville
- 0.33 mi to center
9.3Exceptional
(3 Reviews)
1 Bedroom
1 Bath
5 Guests
904.17 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $135/Night
7 Nights - US $942
Apartment
- Pittsburgh
- ·
- Verona
- 0.89 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1080 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $224/Night
7 Nights - US $1,567
House
- Pittsburgh
- ·
- Oakmont
- 0.59 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
1 Guest
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $126/Night
7 Nights - US $883
Cabin
- Pennsylvania
- ·
- Bairdford
- 5.45 mi to center
9.8Exceptional
(22 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $160/Night
7 Nights - US $1,117
Apartment
- Pennsylvania
- ·
- Bairdford
- 6.92 mi to center
9.2Exceptional
(5 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $146/Night
7 Nights - US $1,021
Luxury Holiday Rentals in Oakmont
Over 81+ Luxury Holiday Rentals in or Near Oakmont
House
- Pittsburgh
- ·
- Plum
- 3.09 mi to center
1 Bedroom
2 Baths
17 Guests
1496.18 ft²
- Parking
- Air Conditioner
Internet
Child Friendly
US $2,187/Night
7 Nights - US $15,309
House
- Pittsburgh
- ·
- Plum
- 1.99 mi to center
3 Bedrooms
3 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $1,710/Night
7 Nights - US $11,970
Apartment
- Pittsburgh
- ·
- Oakmont
- 0.20 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Laundry
US $643/Night
7 Nights - US $4,503
House
- Pennsylvania
- ·
- Bairdford
- 5.46 mi to center
8.0Excellent
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
US $498/Night
7 Nights - US $3,487
Bed & Breakfast
- Pittsburgh
- ·
- Plum
- 3.22 mi to center
10 Bedrooms
10 Baths
19 Guests
433.78 ft²
- Balcony/Terrace
View- Parking
- Air Conditioner
US $413/Night
7 Nights - US $2,890
House
- Pittsburgh
- ·
- Verona
- 0.87 mi to center
9.8Exceptional
(22 Reviews)
5 Bedrooms
2 Baths
11 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $377/Night
7 Nights - US $2,641
House
- Pittsburgh
- ·
- Oakmont
- 0.27 mi to center
10.0Exceptional
(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $340/Night
7 Nights - US $2,378
House
- Pittsburgh
- ·
- Verona
- 0.91 mi to center
10.0Exceptional
(15 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $303/Night
7 Nights - US $2,120
House
- Pittsburgh
- ·
- Oakmont
- 0.49 mi to center
9.2Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
8 Guests
1600 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $298/Night
7 Nights - US $2,086
Top-Rated Holiday Rentals with a Pool in Oakmont
Over 17+ The Best Private Villas and Holiday Rentals in Oakmont with a Pool
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.91 mi to center
9.2Exceptional
(701 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $193/Night
7 Nights - US $1,350
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.91 mi to center
9.2Exceptional
(346 Reviews)
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
US $181/Night
7 Nights - US $1,269
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.90 mi to center
9.1Exceptional
(48 Reviews)
2 Baths
355.21 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
US $236/Night
7 Nights - US $1,653
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.89 mi to center
8.7Fabulous
(155 Reviews)
1 Bath
340.14 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $207/Night
7 Nights - US $1,447
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.89 mi to center
8.0Excellent
(539 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $132/Night
7 Nights - US $926
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.88 mi to center
7.2Very Good
(166 Reviews)
10 Baths
322.92 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
US $157/Night
7 Nights - US $1,099
Hotel
- Pittsburgh
- ·
- O'Hara Township
- 2.19 mi to center
5.8Average
(1007 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $110/Night
7 Nights - US $773
Hotel
- Pittsburgh
- ·
- O'Hara Township
- 2.18 mi to center
5.2Average
(313 Reviews)
6 Baths
250.8 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $89/Night
7 Nights - US $623
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.82 mi to center
10.0Exceptional
(1 Review)
2 Baths
762 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $553/Night
7 Nights - US $3,872
Pet-Friendly Holiday Rentals in Oakmont
Over 24+ Pet-Friendly Holiday Rentals in or Near Oakmont
House
- Pittsburgh
- ·
- Plum
- 1.70 mi to center
10.0Exceptional
(22 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $238/Night
7 Nights - US $1,668
Apartment
- Pittsburgh
- ·
- Springdale
- 0.62 mi to center
9.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Kitchen
US $144/Night
7 Nights - US $1,008
House
- Pittsburgh
- ·
- Plum
- 1.73 mi to center
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $285/Night
7 Nights - US $1,995
Apartment
- Pittsburgh
- ·
- Verona
- 0.97 mi to center
7.4Very Good
(5 Reviews)
1 Bedroom
2 Baths
4 Guests
699.65 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $206/Night
7 Nights - US $1,440
House
- Pittsburgh
- ·
- Plum
- 3.05 mi to center
3 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,428/Night
7 Nights - US $16,997
House
- Pennsylvania
- ·
- Natrona
- 6.90 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $174/Night
7 Nights - US $1,221
Apartment
- Pittsburgh
- ·
- Verona
- 0.97 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
573 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $185/Night
7 Nights - US $1,298
Apartment
- Pennsylvania
- ·
- Wildwood
- 8.82 mi to center
9.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
3 Guests
852 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $146/Night
7 Nights - US $1,025
House
- Pittsburgh
- ·
- Oakmont
- 0.50 mi to center
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,090/Night
7 Nights - US $14,628
Large Holiday Rentals and Private Villas in Oakmont
Over 8+ Large Holiday Rentals and Private Villas in or Near Oakmont
House
- Pittsburgh
- ·
- Plum
- 1.59 mi to center
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $2,467/Night
7 Nights - US $17,272
House
- Pittsburgh
- ·
- Oakmont
- 0.81 mi to center
4 Bedrooms
4 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $5,757/Night
7 Nights - US $40,299
House
- Pittsburgh
- ·
- Dark Hollow
- 0.15 mi to center
6 Bedrooms
4 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $5,700/Night
7 Nights - US $39,900
House
- Pittsburgh
- ·
- Oakmont
- 0.94 mi to center
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $3,990/Night
7 Nights - US $27,930
House
- Pittsburgh
- ·
- Dark Hollow Woods
- 0.06 mi to center
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $3,476/Night
7 Nights - US $24,331
House
- Pittsburgh
- ·
- Plum
- 3.08 mi to center
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $3,449/Night
7 Nights - US $24,140
House
- Pittsburgh
- ·
- Dark Hollow Woods
- 0.06 mi to center
4 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $2,864/Night
7 Nights - US $20,050
House
- Pittsburgh
- ·
- Dark Hollow Woods
- 0.12 mi to center
5 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
Ocean View
US $1,614/Night
7 Nights - US $11,300
Wheelchair Accessible Holiday Homes in Oakmont
Over 4+ Wheelchair Accessible Holiday Homes in or Near Oakmont
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.82 mi to center
2 Baths
680 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $590/Night
7 Nights - US $4,130
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.89 mi to center
6.0Good
(1006 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $118/Night
7 Nights - US $828
Hotel
- Pennsylvania
- ·
- Bairdford
- 6.85 mi to center
5.4Average
(1000 Reviews)
1 Bath
- Breakfast
- Kitchen
- Parking
- Air Conditioner
US $83/Night
7 Nights - US $583
Hotel
- Pittsburgh
- ·
- O'Hara Township
- 2.19 mi to center
5.2Average
(71 Reviews)
1 Bath
- Pool
- Kitchen
- Child Friendly
Wheelchair Accessible
US $89/Night
7 Nights - US $624
Oakmont Private Villas and Holiday Homes Under $200
Over 11+ Oakmont Private Villas and Holiday Homes Under $200
Cottage
- Pittsburgh
- ·
- Verona
- 0.80 mi to center
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $68/Night
7 Nights - US $476
New
House
- Pittsburgh
- ·
- Harwick
- 0.11 mi to center
1 Bedroom
1 Bath
3 Guests
- Balcony/Terrace
- View
- Pet Friendly
- Parking
US $106/Night
7 Nights - US $743
Hotel
- Pittsburgh
- ·
- Harmarville
- 0.40 mi to center
8.0Excellent
(331 Reviews)
1 Bath
- Kitchen
- Parking
- Air Conditioner
- Internet
US $114/Night
7 Nights - US $798
Apartment
- Pittsburgh
- ·
- Oakmont
- 0.86 mi to center
9.0Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Private Pool
- Pool
- Air Conditioner
- Internet
US $168/Night
7 Nights - US $1,179
Hotel
- Pittsburgh
- ·
- Harmarville
- 0.37 mi to center
7.8Very Good
(104 Reviews)
5 Baths
266.94 ft²
- Fireplace/Heating
- Parking
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $700
House
- Pittsburgh
- ·
- Plum
- 2.18 mi to center
2 Bedrooms
2 Baths
4 Guests
1704 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $192/Night
7 Nights - US $1,347
House
- Pittsburgh
- ·
- Verona
- 0.72 mi to center
3 Bedrooms
3 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $190/Night
7 Nights - US $1,332
Apartment
- Pittsburgh
- ·
- Springdale
- 0.68 mi to center
5.0Average
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Child Friendly
US $102/Night
7 Nights - US $714
House
- Pittsburgh
- ·
- Verona
- 1.02 mi to center
2.0Average
(1 Review)
1 Bedroom
4 Baths
3 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $71/Night
7 Nights - US $500
Instantly Bookable Holiday Homes in Oakmont
Over 23+ Instantly Bookable Holiday Homes in or Near Oakmont
New
Apartment
- Pittsburgh
- ·
- Verona
- 0.88 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
- Laundry
US $246/Night
7 Nights - US $1,722
House
- Pennsylvania
- ·
- Bairdford
- 5.46 mi to center
8.0Excellent
(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $440/Night
7 Nights - US $3,080
House
- Pittsburgh
- ·
- Oakmont
- 0.27 mi to center
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $2,719/Night
7 Nights - US $19,032
House
- Pittsburgh
- ·
- Plum
- 2.65 mi to center
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,280/Night
7 Nights - US $15,960
House
- Pittsburgh
- ·
- Upper Oakmont
- 0.25 mi to center
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,451/Night
7 Nights - US $10,158
House
- Pittsburgh
- ·
- Oakmont
- 0.32 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $4,024/Night
7 Nights - US $28,169
House
- Pittsburgh
- ·
- Oakmont
- 0.44 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $812/Night
7 Nights - US $5,686
House
- Pittsburgh
- ·
- Oakmont
- 0.14 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $452/Night
7 Nights - US $3,162
House
- Pittsburgh
- ·
- Oakmont
- 0.64 mi to center
7.6Very Good
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $212/Night
7 Nights - US $1,484
Book a Last Minute Place to Stay in Oakmont
About Casai's Private Villas and Holiday Rentals in Oakmont
Discover more than 90 vacation rentals available in Oakmont. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oakmont.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oakmont, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oakmont. On average, places to stay near Oakmont offer 563.29 ft², with nightly prices averaging US $1,049.
With Casai, finding and comparing holiday rentals in Oakmont is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Oakmont
| Type | Count |
|---|---|
| Vacation Homes | 50 |
| Holiday Apartments | 18 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Oakmont
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oakmont.
Weather in Oakmont, PA
View the weather forecast for Oakmont before booking your Oakmont Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Oakmont, PA
Casai offers a large selection of top attractions around Oakmont . Research things to do on your vacation before you visit Oakmont.
Other Places to Stay in Oakmont, PA
Frequently Asked Questions About Oakmont?
What are the top holiday rentals in Oakmont?
With numerous options available in Oakmont, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oakmont:
- Clean, Fox Chapel Area, 20 Minutes from Downtown Pittsburghn
- Oakmont Inn
- Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
- ✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds
- 4-bedroom modern house in charming Oakmont - close to Country Club and Bakery!
- Retreat in the Heart of a Pittsburgh Rivertown!
- Furnished 2 bedroom 1 bathroom bottom floor unit in Verona
- Robin's Nest
- Charming Riverside Studio in Pittsburgh
- Accessible Family Friendly Safe Locale
Which holiday homes in Oakmont are best for families?
If you're searching for a family-friendly holiday home in Oakmont, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oakmont:
- Comfy three bedroom home near Pitt, CMU and downtown PGH attractions
- 7 Mi to Boyce Park: Family Townhome in Verona!
- 🌟🎨COZY ART HOME in Fox Chapel area by restaurants, bars, shops & hospital!
How many Casai.com holiday rentals are available in Oakmont?
As of 2026, Casai boasts over 90 properties listed in the Oakmont area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oakmont.
Nearby Neighborhood (4)
| Neighborhood | Property Count |
|---|---|
| Plum Vacation Rentals in Pittsburgh, Pennsylvania | 201 |
| Upper Oakmont Vacation Rentals in Pittsburgh, Pennsylvania | 82 |
| Dark Hollow Woods Vacation Rentals in Pittsburgh, Pennsylvania | 87 |
| Dark Hollow Vacation Rentals in Pittsburgh, Pennsylvania | 86 |
People Also Ask
Finding the best prices in Oakmont
Map
