Oakland Vacations from ￥164,842

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was ￥238,535, price is now ￥164,842 per person
￥164,842
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (2,167 reviews)
The hotel is connected to a large mall. lots of shops nearby.

Reviewed on Oct 24, 2025

Beautiful 5bed 3 bath house-Disney Parks

Beautiful 5bed 3 bath house-Disney Parks

4 out of 5
Davenport Lakes
Save 100% on your flight
Price was ￥781,862, price is now ￥477,028 per person
￥477,028
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
No reviews
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ￥274,941, price is now ￥174,379 per person
￥174,379
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.6/10 Exceptional! (1,019 reviews)
All around wonderful stay

Reviewed on Oct 20, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was ￥500,188, price is now ￥337,969 per person
￥337,969
per person
Dec 29 - Jan 4
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9/10 Wonderful! (1,003 reviews)
Clean cottage. Friendly staff.

Reviewed on Oct 8, 2025

Villatel Orlando Resort

Villatel Orlando Resort

4 out of 5
International Drive District
Price was ￥761,209, price is now ￥536,246 per person
￥536,246
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.4/10 Exceptional! (237 reviews)
Clean house and rooms . Prompt attention to any issues .

Reviewed on Oct 20, 2025

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Oakland Hotel Deals

DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is ￥10,586 per night from Nov 2 to Nov 3
￥10,586
￥16,201 total
Nov 2 - Nov 3
includes taxes & fees
7.4/10 Good! (6,235 reviews)
Staff was friendly and nice. Very helpful!

Reviewed on Oct 19, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
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 ￥20,294 per night from Nov 4 to Nov 5
￥20,294
￥22,831 total
Nov 4 - Nov 5
includes taxes & fees
8.8/10 Excellent! (5,483 reviews)
It was a great place to stay.

Reviewed on Oct 24, 2025

Universal's Cabana Bay Beach Resort
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 ￥10,619 per night from Nov 12 to Nov 13
￥10,619
￥11,947 total
Nov 12 - Nov 13
includes taxes & fees
8.4/10 Very Good! (5,126 reviews)
Overall okay experience staying one night. Arrived around mid-night, the lobby was packed with conference goers. Got our room-card, arrived to room, which was pretty far from the lobby (the hotel property is huge). And the key card won't open our door... Walked down and have to drive back to the ...

Reviewed on Oct 20, 2025

Rosen Inn at Pointe Orlando
See all 39,115 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 ￥164,842, 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

5/5(1 review)

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

4/5(6 reviews)

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

Resurrection Catholic Church

5/5(1 review)

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

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥6,355
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

￥4,138
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

￥28,807
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
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.