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 AU$2,500 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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Your Oakland Holiday

Experience all the wonderful things this neighbourhood has to offer with a tailor-made Oakland holiday package. However you see yourself spending your time here, you'll find countless opportunities for fun, adventure and relaxation. When it's time to get out and explore, you'll find a lot of big-name attractions nearby including West Orange Trail, Resurrection Catholic Church and Oakland Nature Preserve. Visit one or all during your trip to Oakland. No matter what your ideal Oakland holiday looks like, you can make it a reality with Expedia.

Our pick of the best Oakland Hotel Deals

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is AU$217 per night from 18 July to 19 July
AU$217
18 July - 19 July
includes taxes & fees
9.2/10 Wonderful! (5,859 reviews)
"Everything was wonderful rooms/suite was extra clean everyone was nice and polite I will come here every time I come to Orlando.Money well spent"

Reviewed on 22 June 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
The price is AU$406 per night from 6 July to 7 July
AU$406
6 July - 7 July
includes taxes & fees
8/10 Very Good! (10,254 reviews)
"Our kids enjoyed the pool and water park."

Reviewed on 22 June 2026

The Grove Resort & Water Park Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 24 June to 25 June
AU$117
24 June - 25 June
includes taxes & fees
9.4/10 Exceptional! (4,526 reviews)
"Drove down from Myrtle Beach with husband, granddaughter and dog. Check in was fantastic and quick. The lobby is fun with plenty to see and the hotel felt super modern. We headed right back out for the night but when we got to our room we realized we didn't have any washcloths and no trash can. By ..."

Reviewed on 22 June 2026

Kompose Boutique Resort at Theme Parks
See all 38,812 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

Disney's Palm Golf Course

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Disney's Palm Golf Course

Activities

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

AU$54
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

AU$256
per adult
Walt Disney World® Resort Theme Park Tickets
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

AU$118
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
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.