Oakland holiday rentals

We found 184 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:15 Jan - 22 Jan

Room
Private kitchen
Living area
Interior
Exceptional
(15 reviews)

Spacious 6-Bedroom Retreat Near Pitt, CMU & Downtown Pittsburgh

Pittsburgh

8% off
AU$6,116
for 7 nights, 1 home
AU$874 per night
includes taxes & fees
Spacious 6-Bedroom Retreat Near Pitt, CMU & Downtown Pittsburgh
Living room - main entrance/front door
Kitchen within the open floor plan allows our guests to be together
Enclosed, private patio - the door goes into the kitchen area
Romeo's Room suite - daybed that is a twin bed with another twin trundle bed
Exceptional
(8 reviews)

Beautiful High-End 4 Bed 3 Bath House, Sleeps 15!

Pittsburgh

11% off
AU$4,621
for 7 nights, 1 home
AU$660 per night
includes taxes & fees
Beautiful High-End 4 Bed 3 Bath House, Sleeps 15!
Living room with unique accent wall
Patio Balcony area with comfy couches and surrounded by trees and skyline
Kitchen with wooden cupboards and marble-designed countertops
8-seater dining table in a cozy dining room
Exceptional
(8 reviews)

Pittsburgh Gem - 5BR - Downtown Deck View

Pittsburgh

15% off
AU$4,068
for 7 nights, 1 home
AU$581 per night
includes taxes & fees
Pittsburgh Gem - 5BR - Downtown Deck View
A welcoming dining space perfect for sharing meals and making memories.
Fully equipped kitchen with easy access to the upper level.
Spacious bedroom designed for a restful night`s sleep.
Cook, gather, and make yourself at home in this inviting kitchen.
Exceptional
(7 reviews)

City Cottage with Yard Sleeps 8

Pittsburgh

10% off
AU$2,412
for 7 nights, 1 home
AU$345 per night
includes taxes & fees
City Cottage with Yard Sleeps 8
Room
Living area
Private kitchen
Exterior detail
Exceptional
(12 reviews)

Iron City of South Side Flats Charming 2-bedroom Unit

Pittsburgh

7% off
AU$1,571
for 7 nights, 1 home
AU$224 per night
includes taxes & fees
Iron City of South Side Flats Charming 2-bedroom Unit
Interior
Private kitchen
Room
Living area
Exceptional
(5 reviews)

Steel City of South Side Flats Charming 2-Bedroom Unit

Pittsburgh

7% off
AU$1,580
for 7 nights, 1 home
AU$226 per night
includes taxes & fees
Steel City of South Side Flats Charming 2-Bedroom Unit

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

When is the best time to visit Oakland for a holiday rental?
The peak season for visiting Oakland stretches from July to September, making it the prime time for holiday rentals in this charming Pennsylvania town. During these months, the pleasant summer weather invites travellers to explore the area's beautiful parks, hiking trails, and vibrant community events.July stands out as the most popular month, bringing with it a lively option filled with festivals and outdoor activities. Temperatures typically hover around 20 to 30 degrees Celsius, great for enjoying leisurely strolls or picnics in the sun. Visitors can take advantage of the local attractions, including the picturesque Lake Oakland, which offers opportunities for swimming, boating, and fishing.If you're looking for a more budget-friendly option, consider visiting in December. While this month may be quieter, it offers a unique charm with festive decorations and seasonal events that showcase the community spirit. Exploring the quaint streets adorned with holiday lights can be a delightful experience, and you'll likely find more availability and attractive rates for holiday rentals.Ultimately, the best time to visit Oakland depends on whether you prefer the bustling energy of the summer months or the tranquil beauty of the winter season.
What are the top attractions in Oakland, Pennsylvania, United States of America?
In Oakland, Pennsylvania, visitors can explore several noteworthy attractions, particularly due to its proximity to the University of Pittsburgh and Carnegie Mellon University. The Carnegie Museums, including the Carnegie Museum of Natural History and the Carnegie Museum of Art, are major draws, offering a rich array of exhibitions and collections. The neighbourhood is also home to the beautiful Phipps Conservatory and Botanical Gardens, where guests can enjoy stunning floral displays and a peaceful environment.Additionally, the area features Schenley Park, which provides extensive walking trails, picnic spots, and sports facilities, making it an excellent location for outdoor activities. The nearby Cathedral of Learning, an iconic symbol of the University of Pittsburgh, is worth a visit for its impressive architecture and the Nationality Rooms that showcase various cultures.
Are all fees included in the Oakland holiday homes prices shown on Stayz?
Stayz 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.
Are there any Oakland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Oakland holiday homes?
You can find great discounts on holiday homes in Oakland on Stayz, 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.
Can I change or cancel my Oakland holiday home booking on Stayz?
To find Oakland holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Oakland?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oakland holiday home?
Book your Oakland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oakland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Oakland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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