Oakland Vacation Packages

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  • Better together

    Save up to CA $4,200 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 Holiday Package Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,178, price is now CA $621 per person
CA $621
per person
Jun 6 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,010 reviews)
Très bien pour le prix

Reviewed on Apr 28, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,611, price is now CA $759 per person
CA $759
per person
Jun 8 - Jun 13
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,243 reviews)
The staff were really nice, attentive respectful. We had a great view wonderful the rooms were excellent comfortable beds. The place felt safe nothing weird the security was on point. The shampoo and soap you’re provided did suck a bit compared to many other places I have stayed at. But it’s okay . We did stay two nights and room service didn't stop by to clean or change sheets but not a deal breaker for us. The outdoor pool and jacuzzi were nice.

Reviewed on Apr 27, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,385, price is now CA $696 per person
CA $696
per person
Jun 16 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (1,647 reviews)
room are clean, and very affordable for the amount of stuff you can do and they have in the villa. The only issue for me is that the water smell like sewer

Reviewed on Apr 28, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,954, price is now CA $1,056 per person
CA $1,056
per person
Jun 13 - Jun 20
found 18 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.4/10 Very Good! (6,225 reviews)
The staff were very friendly. Ever

Reviewed on Apr 29, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,342, price is now CA $747 per person
CA $747
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
7.8/10 Good! (457 reviews)
Would have been nice to have cooking utensils, even just a pot and a pan. People use the suits with the cook tops to try and cut costs of eating out. Traveling people don’t carry around stuff like that and more than likely can’t take it back with them if they need to purchase so it’s wasting money. Also the jacuzzi tub did not work.

Reviewed on Apr 28, 2026

Oakland Hotel Deals

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 CA $147 per night from May 25 to May 26
CA $147
CA $165 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (5,317 reviews)
All good, very comfortable room

Reviewed on Apr 29, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/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 CA $205 per night from May 4 to May 5
CA $205
CA $231 total
May 4 - May 5
includes taxes & fees
9/10 Wonderful! (6,721 reviews)
Everything was excellent. However, the food court is small and very crowded. Expect long wait times at typical meal hours.

Reviewed on Apr 29, 2026

Universal's Cabana Bay Beach Resort
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 CA $226 per night from May 14 to May 15
CA $226
CA $329 total
May 14 - May 15
includes taxes & fees
8/10 Very Good! (9,711 reviews)
There was so much do to at this neat resort. The rooms were updated and very clean. I would definitely stay here again.

Reviewed on Apr 29, 2026

The Grove Resort & Water Park Orlando
See all 39,771 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Frequently asked questions

How much does an Oakland vacation package cost?
Starting from only CA $621, 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

Flamingo Crossings Town Center

You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this walkable area.

Flamingo Crossings Town Center

Surfari Water Park

4.5/5(50 reviews)

Enjoy a fun-filled day at Surfari Water Park as part of your trip to Four Corners. Make time for the shops and golf courses in this family-friendly area.

Surfari Water Park

Central Florida Railroad Museum

You can study the exhibits at Central Florida Railroad Museum, a museum with a story of its own, during your travels 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

CA $53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $230
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Aquatica Orlando

Aquatica Orlando

CA $73
per traveller
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.