Oakland Holidays

Photo by Gregg Yutko

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    Save up to S$1,300 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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Top hotels in Oakland

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 S$193 per night from 6 Jun to 7 Jun
S$193
6 Jun - 7 Jun
includes taxes & fees
9.2/10 Wonderful! (5,555 reviews)
"Great location and nice customer service. I have gone back multiple times."

Reviewed on 23 May, 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
Fully refundableReserve now, pay when you stay
The price is S$308 per night from 25 May to 26 May
S$308
25 May - 26 May
includes taxes & fees
8/10 Very Good! (9,942 reviews)
"There was roaches in our room."

Reviewed on 23 May, 2026

The Grove Resort & Water Park Orlando
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 S$216 per night from 27 May to 28 May
S$216
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (6,832 reviews)
"Great experience! Bus service to Universal resorts was fast and easy. Close drive to Disney properties. Resort area was clean with plenty to do. Pools were great! Food service at resort was convenient. Food was average but worth it for ease. Conner and Kathryn were great at check in and throughout ..."

Reviewed on 23 May, 2026

Universal's Cabana Bay Beach Resort
See all 39,744 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 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 rentals 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.

Popular places to visit

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

Central Florida Railroad Museum

You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your trip to Winter Garden. Amble around this family-friendly area's lakeside or seek out the adventure tours.

Central Florida Railroad Museum

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$49
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

S$239
per adult
Walt Disney World® Resort Theme Park Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

S$194
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.