Oakland holiday homes
We found 185 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Oakland that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and pool. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Oakland
Showing deals for:18 Jul - 25 Jul
Image gallery for Amazingly Homey w/Garage + Outdoor Space! 5B/2B
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Amazingly Homey w/Garage + Outdoor Space! 5B/2B
Pittsburgh, PA
7% off
Price is NZ$6,397
NZ$6,397
NZ$914 per night
includes taxes & fees
Image gallery for PGH Jewel - Modern All New 5B/5B, Near Downtown, Private Parking
1010 out of 10 rating
Exceptional
(12 reviews)
PGH Jewel - Modern All New 5B/5B, Near Downtown, Private Parking
Pittsburgh, PA
7% off
Price is NZ$6,371
NZ$6,371
NZ$910 per night
includes taxes & fees
Image gallery for *New* Loft 3 min to CMU, Pitt Sleeps 4
9.89.8 out of 10 rating
Exceptional
(6 reviews)
*New* Loft 3 min to CMU, Pitt Sleeps 4
Pittsburgh, Pennsylvania
8% off
Price is NZ$2,256
NZ$2,256
NZ$322 per night
includes taxes & fees
Image gallery for Entire Home • Lux Master • Terraces • 4 Car
1010 out of 10 rating
Exceptional
(25 reviews)
Entire Home • Lux Master • Terraces • 4 Car
Pittsburgh, PA
12% off
Price is NZ$6,519
NZ$6,519
NZ$931 per night
includes taxes & fees
Image gallery for Ind Loft Children's Hospital Shadyside Oakland 4
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Ind Loft Children's Hospital Shadyside Oakland 4
Pittsburgh, Pennsylvania
9% off
Price is NZ$2,591
NZ$2,591
NZ$370 per night
includes taxes & fees
Image gallery for King Bed / Free Parking / Arcade / BBQ / Patio
1010 out of 10 rating
Exceptional
(20 reviews)
King Bed / Free Parking / Arcade / BBQ / Patio
Pittsburgh, PA
12% off
Price is NZ$4,602
NZ$4,602
NZ$657 per night
includes taxes & fees
Image gallery for Mathilda Street Trio - Stylish 2BR Apt
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Mathilda Street Trio - Stylish 2BR Apt
Pittsburgh, Pennsylvania
8% off
Price is NZ$2,289
NZ$2,289
NZ$327 per night
includes taxes & fees
Image gallery for Historic Home In The South Side
1010 out of 10 rating
Exceptional
(30 reviews)
Historic Home In The South Side
Pittsburgh, PA
12% off
Price is NZ$2,437
NZ$2,437
NZ$348 per night
includes taxes & fees
Image gallery for King Bed / Free Parking / Arcade / Fire Pit
1010 out of 10 rating
Exceptional
(7 reviews)
King Bed / Free Parking / Arcade / Fire Pit
Pittsburgh, PA
8% off
Price is NZ$4,164
NZ$4,164
NZ$595 per night
includes taxes & fees
Image gallery for Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf
Pittsburgh, PA
8% off
Price is NZ$7,189
NZ$7,189
NZ$1,027 per night
includes taxes & fees
Image gallery for *New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft
9.89.8 out of 10 rating
Exceptional
(41 reviews)
*New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft
Pittsburgh, Pennsylvania
10% off
Price is NZ$9,553
NZ$9,553
NZ$1,365 per night
includes taxes & fees
Image gallery for Apt 2-Downtown Pittsburgh Apt w/ City View Balcony
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Apt 2-Downtown Pittsburgh Apt w/ City View Balcony
Pittsburgh, PA
11% off
Price is NZ$1,930
NZ$1,930
NZ$276 per night
includes taxes & fees
Image gallery for Modern ✌🏾Bedroom House in the ❤️ of Shadyside
9.89.8 out of 10 rating
Exceptional
(33 reviews)
Modern ✌🏾Bedroom House in the ❤️ of Shadyside
Pittsburgh, PA
7% off
Price is NZ$2,591
NZ$2,591
NZ$370 per night
includes taxes & fees
Image gallery for Carey Way Quarters – Modern 2BR Near Carson Street
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Carey Way Quarters – Modern 2BR Near Carson Street
Pittsburgh, Pennsylvania
8% off
Price is NZ$2,995
NZ$2,995
NZ$428 per night
includes taxes & fees
Image gallery for Clean and comfortable 3BR home in the South Side neighborhood
1010 out of 10 rating
Exceptional
(32 reviews)
Clean and comfortable 3BR home in the South Side neighborhood
Pittsburgh, PA
12% off
Price is NZ$3,630
NZ$3,630
NZ$519 per night
includes taxes & fees
Image gallery for Momma Mary's Place @ Lawrenceville
9.49.4 out of 10 rating
Exceptional
(23 reviews)
Momma Mary's Place @ Lawrenceville
Pittsburgh, PA
7% off
Price is NZ$2,546
NZ$2,546
NZ$364 per night
includes taxes & fees
Image gallery for Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking
Pittsburgh, PA
9% off
Price is NZ$3,417
NZ$3,417
NZ$488 per night
includes taxes & fees
Image gallery for Hillman Cancer Center/Children Hospitals Sleeps 6
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Hillman Cancer Center/Children Hospitals Sleeps 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$2,728
NZ$2,728
NZ$390 per night
includes taxes & fees
Image gallery for Industr Loft 5min Shadyside East Liberty Oakland 6
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Industr Loft 5min Shadyside East Liberty Oakland 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$3,305
NZ$3,305
NZ$472 per night
includes taxes & fees
Image gallery for Spacious Loft 2 bedroom in N Oakland 400, sleeps 8
9.69.6 out of 10 rating
Exceptional
(30 reviews)
Spacious Loft 2 bedroom in N Oakland 400, sleeps 8
Pittsburgh, Pennsylvania
10% off
Price is NZ$5,553
NZ$5,553
NZ$793 per night
includes taxes & fees
Image gallery for Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
1010 out of 10 rating
Exceptional
(31 reviews)
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$3,244
NZ$3,244
NZ$463 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Oakland
Map Attractions
2
Carnegie Museum of Natural History
4
Soldiers and Sailors Memorial Hall and Museum
Find the best place to stay - Oakland
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
*New* Loft 7 min to Acrisure Stadium Sleeps 4
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
*New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft
Sleeps 12 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
NEW Gorgeous 4bd near universities Hot tub + Games
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Bright, cozy city flat minutes from Oakland, Downtown Pittsburgh, PPG & Acrisure
Sleeps 6 · 2 bedrooms · 1 bathroom
7.07.0 out of 10
Goodgood
4 reviews(4 reviews)
Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
15 reviews(15 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Oakland?
Apartments are the most popular style of holiday home in Oakland, according to our data. Even if you have something different in mind, Bookabach has properties in many sizes and shapes. Browse our options to find your perfect match.
How much does it cost to rent a holiday home in Oakland?
A range of factors influence how much you’ll pay for a holiday home in Oakland, including the season, type of property and length of stay. Still, all our holiday homes have one thing in common — unbeatable value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Oakland?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Oakland travel dates to view your options on Bookabach. Can’t live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want.
Are there pet-friendly holiday homes in Oakland?
Yes. You can pick from 21 holiday homes that cater to pets in Oakland. Several of our pet-friendly holiday homes come with an outdoor area for your fur child to run around in, complimentary treats, doggie beds and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect pad on Bookabach.
What are popular home amenities in Oakland?
The most popular home amenities people search for in Oakland are a nearby river, a barbecue grill and a garden. Whether you’re going on holiday with your besties, family or even pets, Bookabach holiday homes provide the best amenities for making epic memories with the people who matter most.
Are there large group holiday homes in Oakland?
You can pick from two holiday homes in Oakland that can accommodate 10 or more guests. Whether you’re planning a family holiday or a special event like a birthday party, there’s ample room to get your favourite people together under the same roof.
Are there holiday homes in Oakland that welcome kids?
With 21 family-friendly holiday homes to select from in Oakland, now is a fantastic time to introduce your children to the magic of travel. Check our “Properties good for families” filter box to search for stays loaded with amenities perfect for travelling families, such as kitchens, yards, bunk beds and entertainment units.
What are the top attractions for families in Oakland?
Keep the kids amused at these popular family-friendly attractions in Oakland:
- Pittsburgh Zoo and PPG Aquarium
- Carnegie Science Centre
- Carnegie Museum of Natural History
Are there one-bedroom holiday homes in Oakland?
There are seven one-bedroom properties in Oakland to choose from. A one-bedroom holiday home is a great option if it’s only you and your partner or if you’re holidaying solo. Add in more space, privacy and convenience than a standard hotel, and you’ve got the makings of an unforgettable break.
Can I find two-bedroom holiday homes in Oakland?
Oakland has eight two-bedroom properties to select from. Go for a holiday home with all the space and privacy you need at a fantastic price on Bookabach.
How can I find holiday homes with air conditioning in Oakland?
Oakland has 21 holiday homes where you’ll be able to relax and recharge in air-conditioned comfort. To find a property on Bookabach that comes with this amenity, enter your travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Oakland?
The minimum age allowed can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Oakland you want. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Oakland for?
The amount of time you can book an Oakland holiday home for varies depending on the property. Just enter your travel dates to browse available options that offer long-term stays. They come with all the things you need to make your extended break more enjoyable and comfortable, like kitchens and backyards. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.