Oakland Vacations from ₩966,267

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  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 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

The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Price was ₩1,149,329, price is now ₩966,267 per person
₩966,267
per person
Apr 20 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Orlando (MCO)
9.2/10 Wonderful! (1,174 reviews)
This community and stay was perfect for my family and I. We enjoyed the property and the home was clean. Mariana was super kind and hospitable, her professionalism and her willingness to accommodate was very heartwarming. Caroline was also very kind and helpful. I recommend this property 10/10!

Reviewed on Mar 8, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was ₩1,549,858, price is now ₩1,123,513 per person
₩1,123,513
per person
Apr 20 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Loved it here. House was perfect. Resort great

Reviewed on Mar 17, 2026

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

3.5 out of 5
Price was ₩1,152,909, price is now ₩972,218 per person
₩972,218
per person
Apr 20 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Orlando (MCO)
9.2/10 Wonderful! (1,013 reviews)
We stayed at tower 1, great for us older than 60 people. Everything close by , good walking paths.

Reviewed on Mar 9, 2026

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort

5 out of 5
Golden Oak
Price was ₩2,717,848, price is now ₩2,318,316 per person
₩2,318,316
per person
Apr 20 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Orlando (MCO)
9.6/10 Exceptional! (889 reviews)
Absolutely best resort in Disney area Service exceptional

Reviewed on Mar 20, 2026

Oakland Hotel Deals

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 ₩252,516 per night from Mar 25 to Mar 26
₩252,516
₩366,447 total
Mar 25 - Mar 26
includes taxes & fees
8/10 Very Good! (9,206 reviews)
We enjoyed our stay, clean rooms, great amenities!

Reviewed on Mar 20, 2026

The Grove Resort & Water Park Orlando
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
The price is ₩191,255 per night from Apr 20 to Apr 21
₩191,255
₩215,162 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (4,929 reviews)
Wonderful property and amenities. Almost no need to leave to enjoy a vacation

Reviewed on Mar 20, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
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 ₩144,024 per night from Mar 30 to Mar 31
₩144,024
₩162,027 total
Mar 30 - Mar 31
includes taxes & fees
8.6/10 Excellent! (6,056 reviews)
Amazing place, location and amazing staff! Very pet friendly!

Reviewed on Mar 21, 2026

Rosen Inn at Pointe Orlando
See all 39,348 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 vacation package cost?
Starting from only ₩966,267, a vacation 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 vacation 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 travelers.
How far in advance should I book my Oakland vacation?
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 traveling 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 vacation rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with an Oakland Expedia vacation 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 vacation package?
You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Oakland vacation 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

Disney's Magnolia Golf Course

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

Disney's Magnolia Golf Course
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.