Oakland Vacations from ￥279,789

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The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ￥354,064, price is now ￥279,789 per person
￥279,789
per person
Jun 2 - Jun 8
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (1,068 reviews)
great place , highly recommended

Reviewed on Mar 30, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was ￥489,822, price is now ￥301,397 per person
￥301,397
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
The room I stayed in was clean and comfortable. I liked the fact it had a small balcony, although I did not utilize it. Most properties I've stayed at in the past have an available electrical outlet near the bed or nightstand. Due to the apparent age of this building however, the room did not have a lot of electrical outlets, so I had to plug my phone in to charge on the floor, near the tv.

Reviewed on Mar 29, 2026

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5 out of 5
Price was ￥425,662, price is now ￥331,760 per person
￥331,760
per person
May 21 - May 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (475 reviews)
This is a really nice hotel and the service staff were great! The only issue we had was there were no washcloths until our last night there. Also, when we came in our sink drain would not open and someone had to come fix that our second day there. Besides those things, I really have no complaints with the hotel!

Reviewed on Mar 31, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was ￥417,768, price is now ￥326,442 per person
￥326,442
per person
Jun 23 - Jun 27
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Friendly staff. Great location. Villa was amazing

Reviewed on Mar 28, 2026

Hilton Orlando Lake Buena Vista - Disney Springs® Area

Hilton Orlando Lake Buena Vista - Disney Springs® Area

4 out of 5
Price was ￥360,035, price is now ￥283,326 per person
￥283,326
per person
May 21 - May 23
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.6/10 Excellent! (1,566 reviews)
Hotel is very clean, friendly staff, easy access to Disney springs and buses for Disney parks. My only real complaint is how expensive everything is in their market/ food area and at the bar. An energy drink was $7 and breakfast was around $30 a person. We were there with a high school show choir and many of the kids skipped breakfast due to the cost. Seems excessive!

Reviewed on Mar 29, 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 ￥25,050 per night from Apr 21 to Apr 22
￥25,050
￥36,991 total
Apr 21 - Apr 22
includes taxes & fees
8/10 Very Good! (9,354 reviews)
Booked this resort, to try something different from the usual hotel we frequently stay at when visiting Orlando. I have to admit, the photos online make this place seem like a steal for $250 a night. However, after staying there, I am not sure I would again. Came during Spring Break and it was insanely ...

Reviewed on Mar 31, 2026

The Grove Resort & Water Park 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 ￥15,832 per night from Apr 21 to Apr 22
￥15,832
￥17,812 total
Apr 21 - Apr 22
includes taxes & fees
8.6/10 Excellent! (6,183 reviews)
Ac kept room cool. I needed an extra blanket press “0” on the room phone and asked for one and got it within 10 minutes to my room!

Reviewed on Mar 31, 2026

Rosen Inn at Pointe 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
Fully refundableReserve now, pay when you stay
The price is ￥25,570 per night from Apr 26 to Apr 27
￥25,570
￥28,766 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (5,057 reviews)
I booked at the Sheraton Vistana as an alternative to the highly overpriced rooms being offered for the conference I attended not far away. Not only was the room we stayed in at Sheraton Vistana a fraction of the price I would’ve paid to stay at the hotel the conference was being held, it was a much ...

Reviewed on Mar 31, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 39,671 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 ￥279,789, 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 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

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

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

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

￥6,113
per traveler
86% 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

￥4,327
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

￥8,398
per traveler
84% of travellers recommend
Aquatica Orlando
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.