Oakland Holidays from NZ$3,730

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Top Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4 out of 5
Orange Lake
Price was NZ$4,694, price is now NZ$3,730 per person
NZ$3,730
per person
22 Dec - 28 Dec
found 17 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
8.8/10 Excellent! (2,420 reviews)
Very clean resort. Heavy in the time share promos. TVs are pretty small. Had a 3 br/3 ba rental. It was nice distributed. Although noise can carry from one bedroom to other.

Reviewed on 6 Oct 2025

Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

4 out of 5
Price was NZ$6,284, price is now NZ$4,350 per person
NZ$4,350
per person
22 Dec - 28 Dec
found 17 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9.2/10 Wonderful! (1,145 reviews)
Spacious accommodations near Disney, with some amenities.

Reviewed on 4 June 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was NZ$5,795, price is now NZ$4,079 per person
NZ$4,079
per person
22 Dec - 28 Dec
found 17 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9/10 Wonderful! (1,001 reviews)
Cottage was immaculate and was very large. Close to Target for groceries and the shuttle service was excellent and very convenient.

Reviewed on 16 Sept 2025

Conrad Orlando at Evermore

Conrad Orlando at Evermore

5 out of 5
Price was NZ$5,843, price is now NZ$4,645 per person
NZ$4,645
per person
22 Dec - 28 Dec
found 17 hours ago
Return flight included
Wellington (WLG) to Orlando (MCO)
9.6/10 Exceptional! (282 reviews)
I loved the cleanliness of the entire property. Staff was very professional and polite.

Reviewed on 5 Oct 2025

Our guide on 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

Our pick of the best Oakland Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
The price is NZ$172 per night from 2 Nov to 3 Nov
NZ$172
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very Good! (6,727 reviews)
"The stay was over all pleasant but the staff at the lobby took forever to take care of the guests. Also, we have a child and needed to warm up milk constantly. The microwave is all the way in the game room making it a hassle to get there. There was renovation going on at the hotel therefore they ..."

Reviewed on 30 Sept 2025

DoubleTree by Hilton at the Entrance to Universal 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 NZ$270 per night from 5 Nov to 6 Nov
NZ$270
5 Nov - 6 Nov
includes taxes & fees
8.8/10 Excellent! (5,356 reviews)
"Great for families"

Reviewed on 1 Oct 2025

Universal's Cabana Bay Beach Resort
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 NZ$191 per night from 27 Oct to 28 Oct
NZ$191
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (3,595 reviews)
"Cannot say enough, good things about this spot!"

Reviewed on 1 Oct 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
See all 39,247 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 NZ$3,730, 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 homes 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.

Discover the most popular places to visit in Oakland

Orange County National Golf Club

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Orange County National Golf Club

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

Activities

Aquatica Orlando

Aquatica Orlando

NZ$88
per traveller
82% of travellers recommend
Aquatica Orlando
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

NZ$334
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Orlando: 7-D Dark Ride Entry Ticket

Orlando: 7-D Dark Ride Entry Ticket

NZ$20
per adult
90% of travellers recommend
Orlando: 7-D Dark Ride Entry Ticket
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.