Oakland Holidays

Photo by Gregg Yutko

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Price found within the past 48 hours. Click for updated prices.
I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
International Drive District
Price was €1,301, price is now €856 per person
€856
per person
7 Mar - 14 Mar
found 12 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
6.8/10 (1,002 reviews)
The stuff was great, and the breakfast was good with some options. Our room was clean, but They will be able to move us to another room due to a heat problem. Overall, I would rate it at nine.

Reviewed on 17 Dec 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was €2,186, price is now €1,248 per person
€1,248
per person
7 Mar - 14 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Garbage bags were cheap. Thats my o ly complaint. It was perfect and will stay again

Reviewed on 18 Dec 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was €1,663, price is now €1,042 per person
€1,042
per person
7 Mar - 14 Mar
found 12 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (1,002 reviews)
Exceeded my expectations

Reviewed on 21 Dec 2025

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Price was €3,670, price is now €2,364 per person
€2,364
per person
7 Mar - 14 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.6/10 Exceptional! (489 reviews)
Wonderful experience

Reviewed on 15 Dec 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Price was €1,554, price is now €1,029 per person
€1,029
per person
7 Mar - 14 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
8.8/10 Excellent! (1,422 reviews)
Too far away from the main resort and amenities.. Sandy ridge is too far.

Reviewed on 17 Dec 2025

Top hotels in Oakland

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 €127 per night from 6 Jan to 7 Jan
€127
6 Jan - 7 Jan 2026
includes taxes & fees
8.8/10 Excellent! (5,849 reviews)
La habitación limpia

Reviewed on 25 Dec 2025

Universal's Cabana Bay Beach Resort
Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
The price is €77 per night from 5 Jan to 6 Jan
€77
5 Jan - 6 Jan 2026
includes taxes & fees
7.2/10 Good! (3,939 reviews)
I thought that the hotel gave good value for the price. The room decor was basic but clean and spacious. The beds were comfortable. The room had a large TV, small fridge, microwave and safe. The pool looked inviting. The wi-fi was excellent. The front staff were very nice. I was originally assigned ...

Reviewed on 24 Dec 2025

Wyndham I-Drive Avanti Resort & Conference Center
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 €93 per night from 14 Jan to 15 Jan
€93
14 Jan - 15 Jan 2026
includes taxes & fees
8.4/10 Very Good! (5,425 reviews)
The breakfast staff were unprofessional and chatted throughout our time there.

Reviewed on 24 Dec 2025

Rosen Inn at Pointe Orlando
See all 39,796 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 €856, 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

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

Winter Garden Art Association

Rich with history, Winter Garden Art Association is a cultural attraction worth visiting in Winter Garden. Stroll along the lakeside in this family-friendly area or visit its top-notch restaurants.

Winter Garden Art Association

Carter Family Bowl

Enjoy a trip to Carter Family Bowl and popular activities such as taking adventure tours in Winter Garden. Amble around this family-friendly area's seaside and enjoy its top-notch restaurants.

Carter Family Bowl

Things to do

Aquatica Orlando

Aquatica Orlando

€45
per traveller
84% of travellers recommend
Aquatica Orlando
Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

€390
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Walt Disney World® Resort Theme Park Tickets

Walt Disney World® Resort Theme Park Tickets

€170
per adult
88% of travellers recommend
Walt Disney World® 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.