Oakland Holidays

Photo by Gregg Yutko
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
New York (NYC) to Orlando (MCO)
8.6/10 Excellent! (1,493 reviews)
Time and time again, I say Melia is one of the best places you can stay.

Reviewed on 22 Jun, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
New York (NYC) to Orlando (MCO)
8.6/10 Excellent! (1,000 reviews)
Friendly staff, and very convenient to get around

Reviewed on 24 Jun, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
New York (NYC) to Orlando (MCO)
8.2/10 Very Good! (5,034 reviews)
Besides the neighbors being a little loud in the morning, it was perfect. Not much you can do about the noise because it’s their vacation too so no big deal. But the hotel was amazing. The pools were all clean and had good temperatures as well. And it was not too far away from any attractions nearby. There was also a convenient walmart just down the road and lots of food options from cheap to expensive just further down. 10/10 experience.

Reviewed on 24 Jun, 2025

Hilton Grand Vacations Club Tuscany Village Orlando

Hilton Grand Vacations Club Tuscany Village Orlando

4 out of 5
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
New York (NYC) to Orlando (MCO)
9/10 Wonderful! (1,427 reviews)
They were great and brought a hair dryer to our room when I couldn’t find one. However, we were told we could request a late checkout and stay until 11:30 being our flight was later in the day. When I requested the late checkout they told me we could stay until 10:30- only a 1/2 hr after regular check out. Disappointed! We are there 5 nights and they couldn’t let us stay another hour- check isn’t until 4pm for incoming guests.

Reviewed on 22 Jun, 2025

Buena Vista Suites Orlando

Buena Vista Suites Orlando

4 out of 5
per person
7 Sept - 14 Sept
found 1 day ago
Return flight included
New York (NYC) to Orlando (MCO)
9.2/10 Wonderful! (1,724 reviews)
Great place to stay.

Reviewed on 23 Jun, 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

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
The price is S$169 per night from 16 Jul to 17 Jul
S$169
16 Jul - 17 Jul
includes taxes & fees
9.2/10 Wonderful! (3,095 reviews)
"I enjoyed the pool area. The"

Reviewed on 22 Jun, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Marriott's Grande Vista
Marriott's Grande Vista
4 out of 5
5925 Avenida Vista, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 14 Jul to 15 Jul
S$149
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (2,530 reviews)
"The room and areas around were clean and safe"

Reviewed on 21 Jun, 2025

Marriott's Grande Vista
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 S$222 per night from 25 Jun to 26 Jun
S$222
25 Jun - 26 Jun
includes taxes & fees
8.4/10 Very Good! (4,528 reviews)
"Empleados amables, áreas comunes y la habitación estaban muy limpios. Solo deben actualizar un poco el hotel. Por lo demás todo muy bien."

Reviewed on 21 Jun, 2025

Rosen Inn at Pointe Orlando
See all 38,006 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 S$556, 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

Eco-Kayak Tour

Guided Eco-Paddle

S$76
per traveller
Guided Eco-Paddle
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$98
per traveller
84% of travellers recommend
LEGOLAND® Florida Tickets
Old Town Kissimmee: Attraction and Meal Combo Offers

Old Town Kissimmee: Attraction and Meal Combo Offers

S$19
per adult
80% of travellers recommend
Old Town Kissimmee: Attraction and Meal Combo Offers
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.