Oakland holiday lettings

We found 169 holiday rentals — enter your dates for availability

Discover a selection of 7 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:30 Jan - 6 Feb

Image gallery for Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

Living area
9.4 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)

Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

Pittsburgh, PA

7% off
Price is £2,023
for 7 nights, 1 home
£289 per night
includes taxes & fees
Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

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Frequently asked questions

What is the most popular type of holiday rental in Oakland?
In Oakland, apartments are the most popular type of holiday rental, with around 44 available throughout the area. These apartments are often situated in lively neighbourhoods close to various amenities and attractions, providing a convenient base for exploring the local culture. Most rooms feature fully equipped kitchens, comfortable living areas, and modern furnishings, making them ideal for both short and extended stays.
How much does it cost to rent a holiday home in Oakland?
Prices for holiday rentals in Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oakland holiday house rentals?
You can find great discounts on house rentals in Oakland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Oakland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oakland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Oakland?
A long-stay holiday rental in Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Oakland for a holiday rental?
The best time to visit Oakland for a holiday rental is during the peak season from July to September, when the area comes alive with vibrant summer activities. This period is particularly appealing for families and outdoor enthusiasts, as the warm weather, typically in the mid to high 20s Celsius, creates ideal conditions for exploring local parks and engaging in recreational activities like hiking and biking.

July stands out as the most popular month, attracting visitors who are keen to enjoy the community events and festivals that frequently take place. The atmosphere is energetic, making it a great backdrop for those eager to soak up the local culture while participating in outdoor adventures.

For those looking for a more budget-friendly option, consider planning your visit in December. While this month is in low season, it offers a unique charm with festive decorations and a quieter pace, allowing for a more relaxed exploration of the area.
Are there any remote work holiday rentals in Oakland?
In Oakland, Pennsylvania, there are numerous remote work holiday rentals available, with around 48 options to choose from. This area is known for its vibrant community and convenient access to local amenities. Many of the properties come equipped with essential remote work amenities such as Wi-Fi, dedicated desk spaces, and comfortable office setups, ensuring a productive environment for those working away from home.

Travellers can expect accommodations featuring well-appointed living areas, full kitchens for meal preparation, and sometimes even extra features like separate office rooms or ergonomic furniture to enhance their work-from-home experience. The proximity to local cafes and parks also provides excellent opportunities for breaks and relaxation after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oakland holiday rental?
Book your Oakland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oakland?
In Oakland, Pennsylvania, visitors can enjoy a range of attractions primarily centred around the University of Pittsburgh and Carnegie Mellon University. The nearby Phipps Conservatory and Botanical Gardens offer a beautiful escape with its stunning floral displays and seasonal exhibitions, great for nature lovers. Just a short stroll away, the Carnegie Museum of Natural History and the Carnegie Museum of Art provide enriching cultural experiences.
Can I change or cancel my Oakland home rental booking on Vrbo?
To find Oakland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oakland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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