Oakland Holidays

Photo by Gregg Yutko

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Top hotels in Oakland

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 S$342 per night from 22 Apr to 23 Apr
S$342
22 Apr - 23 Apr
includes taxes & fees
8/10 Very Good! (9,443 reviews)
Honestly, the resort itself is not clean. The hallways going to our room was so dirty, we took three flights of stairs rather than the elevator because it was so filthy and the floor was falling apart. We wanted to sit and enjoy the nice lounge area by the springs pool bar but there was garbage piled ...

Reviewed on 8 Apr, 2026

The Grove Resort & Water Park Orlando
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$207 per night from 4 May to 5 May
S$207
4 May - 5 May
includes taxes & fees
9.2/10 Wonderful! (5,118 reviews)
Extremely pleased with this facility. From check in to check out, everything exceeded our expectations. We will stay here again in the future.

Reviewed on 8 Apr, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

3 out of 5
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
The price is S$143 per night from 13 Apr to 14 Apr
S$143
13 Apr - 14 Apr
includes taxes & fees
9.4/10 Exceptional! (3,461 reviews)
La habitación espaciosa y limpia, el staff con buena actitud siempre. Lo que no sabía fue que al rentar con Expedia cobran $15 adicionales por Parqueo por noche, es mejor reservar directo con el hotel. Las instalaciones muy buenas, las piscinas, el río lento, saunas, gimnasio. Muy bien ubicado. Wifi ...

Reviewed on 8 Apr, 2026

Kompose Boutique Resort at Theme Parks
See all 39,289 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 , 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

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

S$49
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

S$248
per adult
78% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

S$35
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. 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.