Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Gregg Yutko

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Our pick of the best Oakland Hotel Deals

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 7 Jan to 8 Jan
NZ$259
7 Jan - 8 Jan
includes taxes & fees
8.8/10 Excellent! (6,002 reviews)
Great place

Reviewed on 5 Jan 2026

Universal's Cabana Bay Beach Resort
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 14 Jan to 15 Jan
NZ$156
14 Jan - 15 Jan
includes taxes & fees
7.2/10 Good! (4,054 reviews)
The hotel grounds were pretty great, once we figured out how to get to our room around the entire backside of the building. Phone inside our room didn't work, so calling the front desk when we needed something was a chore. Hair dryer in room didn't work. Room service for cleaning isn't done unless ...

Reviewed on 6 Jan 2026

Wyndham I-Drive Avanti Resort & Conference Center
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
The price is NZ$152 per night from 26 Jan to 27 Jan
NZ$152
26 Jan - 27 Jan
includes taxes & fees
8.4/10 Very Good! (5,502 reviews)
Clean room for budget stay

Reviewed on 2 Jan 2026

Rosen Inn at Pointe Orlando
See all 39,629 properties in Oakland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does an Oakland holiday package cost?
Starting from only , a holiday package is your portal to affordable travel. Customize your Oakland escape by picking from our great range of airfares, hotels and rental cars.
How do I get a cheap travel package to Oakland?
You'll save a ton of money if you bundle your flights, hotels and car rentals into an Oakland holiday package. Sometimes cheap packages mean fewer options. But not with Expedia. We offer over 550 partner airlines and 1 000 000 hotels worldwide, which means you'll always have plenty of options to choose from. Like to save even more? Add some interesting activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Oakland?
With loads to explore in Oakland, we recommend you lock in a hotel near its attractions. West Orange Trail, Garden Theatre and Winter Garden Heritage Museum are some popular ones to add to your itinerary.
What are the top hotels in Oakland?
Whether you'll be staying for one night or longer in Oakland, you'll get a good night's rest at The Oak View Place. This place is the first choice for many travellers.
How far in advance should I book my Oakland holiday?
While prices change from time to time, we generally recommend booking your seats as soon as possible. Most international fares become available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Oakland sometimes appear only weeks before departure.
What does an Expedia Oakland travel package include?
Rental cars, hotels and flights, or any combination of them — the choice is all yours! Whether you're exploring Oakland on a family road trip or travelling with your friends, there's a package to match your budget and style. Once you've made your booking, why not add on one or two tours as well?
What should I know before booking an Oakland travel package?
Locking in all the parts of your getaway together is a simple way to save. Combine car rentals, airfares and hotels into a tidy package. But you're not limited to hotels. Expedia features all kinds of properties, including holiday homes like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with an Oakland Expedia holiday package?
Definitely. Expedia has more than 550 airline partners to pick from worldwide. With all that choice at your fingertips, finding the perfect carrier to fly you to Oakland will be a cinch.
If I'm not able to travel, can I cancel my Oakland holiday package?
You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Oakland holiday package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for further information.

Discover the most popular places to visit in Oakland

Orange County National Golf Club

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Orange County National Golf Club

Resurrection Catholic Church

After visiting Resurrection Catholic Church, make a plan to see the other sights and activities in Winter Garden. Amble around this family-friendly area's seaside or seek out the adventure tours.

Resurrection Catholic Church

Activities

Aquatica Orlando

Aquatica Orlando

NZ$91
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$347
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

NZ$21
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
See all activities in Winter Garden
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.