Oakland Holidays

Photo by Gregg Yutko

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Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was €525, price is now €328 per person
€328
per person
9 Apr - 15 Apr
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
The hotel was quiet. It was on the lake which made a nice place to sit and enjoy nature.

Reviewed on 13 Feb 2026

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was €1,583, price is now €815 per person
€815
per person
9 Apr - 15 Apr
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Great location, property and resort. Had a great time

Reviewed on 6 Feb 2026

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Price was €951, price is now €604 per person
€604
per person
9 Apr - 15 Apr
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,422 reviews)
Rooms were ready and as always perfect Staff at check in very helpful

Reviewed on 3 Feb 2026

Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
Price was €1,189, price is now €768 per person
€768
per person
9 Apr - 15 Apr
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (152 reviews)
Exactly what we needed for our stay in Disney. Was first time we have stayed off property and besides not getting in to the park early, this place was great. It rained on us every day at the park and was nice to be able to through our jacket in the dryer! On negative i will say is the washer and dryer was loud HA! But other than that place had everythign we needed. Oh and fyi this place was not 3 bed rooms. It was 4! Maybe because it didtn have a bathroom? Not sure but was 4 bedroom 3 and half bath. HA kids liked havign there own rooms with own bathrooms. And so did I! Was thankful we was not crammed on an on park hotel with one room and one bathroom! Had 2 masters with Kings, one upstairs one down, and then the other 2 rooms was up stairs with one being two twins with bathroom then the other room was just a bunk. Would stay here again for sure.

Reviewed on 9 Oct 2025

Parkway International Resort

Parkway International Resort

3 out of 5
Price was €669, price is now €433 per person
€433
per person
9 Apr - 15 Apr
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (2,052 reviews)
Check in was easy, room was large, clean, and close to the Disney parks.

Reviewed on 13 Feb 2026

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 €124 per night from 15 Mar to 16 Mar
€124
15 Mar - 16 Mar
includes taxes & fees
9.2/10 Wonderful! (4,560 reviews)
Amazing resort for the price you can’t beat it!

Reviewed on 10 Feb 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 €207 per night from 1 Mar to 2 Mar
€207
1 Mar - 2 Mar
includes taxes & fees
8/10 Very Good! (9,004 reviews)
Everything ws perfect

Reviewed on 12 Feb 2026

The Grove Resort & Water Park Orlando
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
Fully refundable
The price is €119 per night from 12 Mar to 13 Mar
€119
12 Mar - 13 Mar
includes taxes & fees
8.4/10 Very Good! (6,937 reviews)
Not only are the rooms very clean but the staff is extremely nice and the free bus to universal was a great plus. I would recommend this hotel to everyone

Reviewed on 10 Feb 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 39,430 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 €328, 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

Garden Theatre

Enjoy a show at Garden Theatre, a theatre with a story to tell in Winter Garden. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Garden Theatre

Things to do

Universal Orlando Resort

Universal Orlando Resort Theme Park Tickets

€486
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

€44
per traveller
84% of travellers recommend
Aquatica Orlando
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

€23
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
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.