Photo by Gregg Yutko

Oakland holiday rentals

We found 413 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Oakland that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you need and want for your stay, which might include parking and a garden. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Oakland

Showing deals for:25 Dec - 1 Jan

Private kitchen
Dining
Outdoor dining
Living area
Wonderful
(21 reviews)

Orlando 4 BR Home Centrally Located on Dead End St

Orlando

8% off
AU$3,490
for 7 nights, 1 home
AU$499 per night
includes taxes & fees
Orlando 4 BR Home Centrally Located on Dead End St
Exterior
Living room with sky windows for natural sunlight
Back Yard
Front yard
Exceptional
(6 reviews)

Orlando 1 Acre 4 BD Home Central Near Universal

Orlando

12% off
AU$4,071
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Orlando 1 Acre 4 BD Home Central Near Universal
Patio area and backyard
Exterior
Kitchen
Foosball Table
Exceptional
(7 reviews)

Orlando 20 Guest Villa Centrally Located with Game Room

Windermere

16% off
AU$4,910
for 7 nights, 1 home
AU$701 per night
includes taxes & fees
Orlando 20 Guest Villa Centrally Located with Game Room
Terrace/patio
Private kitchen
Room
Interior
Exceptional
(11 reviews)

Modern Brick Rural Home

Clermont

8% off
AU$3,406
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Modern Brick Rural Home
Pool
Private kitchen
Dining
Living area
Exceptional
(6 reviews)

The Orlando Oasis with Private Pool

Orlando

8% off
AU$4,564
for 7 nights, 1 home
AU$652 per night
includes taxes & fees
The Orlando Oasis with Private Pool
Room
Private kitchen
Interior
Outdoor dining
Excellent
(7 reviews)

Charming studio in superb Clermont with AC, WiFi

Clermont

8% off
AU$1,298
for 7 nights, 1 apartment
AU$185 per night
includes taxes & fees
Charming studio in superb Clermont with AC, WiFi
Living Room Pull Sectional accommodates up to 2
Living area
Master Bedroom
Private kitchen
Exceptional
(6 reviews)

Visiting Family, Lakes, Golf, Olympus, the Mouse?

Clermont

6% off
AU$1,782
for 7 nights, 1 apartment
AU$255 per night
includes taxes & fees
Visiting Family, Lakes, Golf, Olympus, the Mouse?

  • 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 best time to visit Oakland, Florida, for a holiday rental is during the peak season from January to March. This period is especially popular, with visitors flocking to enjoy the sunny weather and vibrant local attractions. With temperatures ranging from 10 to 25 degrees Celsius, the climate is great for outdoor activities such as strolling through the beautiful parks or enjoying watersports on the nearby lakes.March stands out as the most popular month, offering a lively option filled with community events and festivals. It's an ideal time for families and friends to gather, as well as for those looking to embrace the festive spirit of springtime in Florida.For those who are more budget-conscious or seeking a quieter experience, consider planning your visit in August. While it may be less bustling, this month allows for a more relaxed vibe and the opportunity to enjoy the natural beauty of the area without the crowds.No matter when you choose to visit Oakland, you'll find a welcoming community and a variety of activities to make your stay memorable.
What are the top attractions in Oakland, Florida, United States of America?
In Oakland, Florida, visitors can explore a variety of attractions that highlight the area's natural beauty and local charm. The historic downtown area features quaint shops and restaurants, providing a taste of the local culture. Nearby, the beautiful Lake Apopka offers opportunities for outdoor activities such as birdwatching, hiking, and cycling along the Lake Apopka Loop Trail, which is popular for its scenic views and wildlife.The local parks, such as the Oakland Nature Preserve, provide a serene setting for walking trails and nature observation, great for families and nature enthusiasts. Additionally, the community often hosts events and festivals that showcase local artists and craftspeople, adding to the vibrant setting of this small town.
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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