Oakland Vacation Packages
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Top Holiday Package Deals in Oakland
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,496
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
The unit itself is beautiful. The bedrooms and bathrooms are gorgeous with really nice furnishings. The showers are really nice and each bedroom has an attached bathroom, which is very convenient.
There were a few issues with cleanliness in the unit and the pool. We had stained washcloths in one bathroom, the sofa fabric is pilling and we found several items on the kitchen floor that hadn't been swept up. The pool filter doesn't appear to work well at all. We continually skimmed the pool but there was still dirt and leaves in the bottom of the pool that never went away.
The pictures in the listing show the pool as having an attached hot tub. It does not. It also shows loungers by the pool, but there are none. I did call the front desk to advise them of this. I asked for loungers to be delivered but they will not do that as it seems it's the responsibility of the owners to provide those. They didn't have much to say about the pool not having the hot tub, even though it is advertised as having one so that was disappointing.
The resort lobby is beautiful and check in was fairly easy. The resort pools and hot tubs were very nice as well. The pool bar food and drinks are expensive ($40 for a drink and hummus appetizer) and an automatic 20% gratuity is automatically added to all orders. Something to keep in mind.
Overall, we had a great stay and would definitely do it again, although I would not rent this particular unit the next time.
Reviewed on Sep 14, 2026
Westgate Lakes Resort & Spa Universal Studios Area
CA $695
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.4/10 Very good! (7,020 reviews)
cleaneless can be improved. also the access to the inside water park cost 20$ a person, but in case of bad weather they closed and there is no refund.
Reviewed on Sep 15, 2026
Westgate Blue Tree Resort in Lake Buena Vista
CA $652
per person
Dec 2 - Dec 8
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The stay was immaculate. It was secluded and quiet. The perfect resting place for celebrating my husband’s birthday. We were near everything we wanted to enjoy. The staff was amazing; Morgan gave an excellent introduction to the property and we enjoyed throughly and hassle free. We will be returning in November for a concert after this amazing experience! Our pets enjoyed the property and the quiet and calm ambiance really helped them to relax into a new space.
Reviewed on Sep 14, 2026
Oakland Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $190
CA $214 total
Oct 7 - Oct 8
includes taxes & fees
9.2/10 Wonderful! (6,753 reviews)
"Sort of solicited checking in and out. Nice properties."
Reviewed on Sep 16, 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
CA $133
CA $150 total
Oct 9 - Oct 10
includes taxes & fees
9/10 Wonderful! (4,968 reviews)
"Marriott has a great location with close proximity to Sea World. I was a bit surprised by the amount of the required deposit ($500) at check in.. In addition to the $30 per day self-parking charge (valet is NOT available); I was out of $750 at check in. That meant I essentially paid for my stay once ..."
Reviewed on Sep 16, 2026
Avanti International Resort
8738 International Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $99
CA $139 total
Sep 17 - Sep 18
includes taxes & fees
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 CA $543, 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.
Things to do
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $194
per adult
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
CA $38
per adult
92% of travellers recommend
WonderWorks All Access After Dark
CA $38
per traveller
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.