Oakland Holidays from £703

Book a Hotel + Flight or Car together to unlock savings

Photo by Gregg Yutko

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Oakland Holiday

Organising your next exciting getaway just got simpler with a holiday package to Oakland. Immerse yourself in everything this neighbourhood has to offer while creating precious memories you'll treasure. Your trip to Oakland wouldn't be complete without a visit to top attractions nearby such as West Orange Trail, Garden Theatre and Winter Garden Heritage Museum. Expedia is here to put your travel plans into action. Book your dream Oakland holiday today.

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

Westgate Town Center Resort

4 out of 5
Price was £1,101, price is now £703 per person
£703
per person
13 May - 20 May
found 3 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.2/10 Very Good! (1,554 reviews)
We stayed at the resort while we traveled to the Disney parks and it was perfect for our family of 4. We had a 2 bedroom suite and it had a nice kitchen area and spacious balcony. There were a lot of other families staying nearby and we saw a lot of activities and events going on around the resort. We unfortunately didn’t get to partake since some of them had to be cancelled due to bad weather during our vacation week. The staff was really helpful and made sure our room had the same number of beds listed in our reservation description. It also had a security area you had to go through which added extra peace of mind.

Reviewed on 12 Apr 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was £2,123, price is now £1,268 per person
£1,268
per person
16 May - 23 May
found 1 day ago
Return flight included
London (LON) to Orlando (MCO)
9.2/10 Wonderful! (1,005 reviews)
Hot tub did not work and took 2 days and multiple calls to get it fixed. The grounds were subpar from last time we stayed there, no refreshed landscaping. Usually is very nice but this time felt like a PCB vibe. Probably the last time staying here.

Reviewed on 11 Apr 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was £1,466, price is now £945 per person
£945
per person
23 Jun - 30 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Orlando (MCO)
9.2/10 Wonderful! (1,336 reviews)
I love that hotel I will be staying there again. Very convenient and close to everything

Reviewed on 5 Apr 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was £1,126, price is now £742 per person
£742
per person
13 May - 20 May
found 3 hours ago
Return flight included
London (LON) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
Its always a pleasure to stay at Westgate Bluetree! Clean rooms and property, friendly staff and very conveniently located near dusney, outlets, grocery stores and more!!

Reviewed on 1 Apr 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 £1,237, price is now £854 per person
£854
per person
23 May - 29 May
found 7 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
7.8/10 Good! (413 reviews)
The hotel had a very nice location. The breakfast was terrible. The elevators didn’t work only one. The two bars that they had on property were never open and we were there for one week. The location is probably the best part of the resort.

Reviewed on 11 Apr 2026

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 £186 per night from 19 Apr to 20 Apr
£186
19 Apr - 20 Apr
includes taxes & fees
8/10 Very Good! (9,512 reviews)
Internet was slow.

Reviewed on 12 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
Fully refundableReserve now, pay when you stay
The price is £103 per night from 4 May to 5 May
£103
4 May - 5 May
includes taxes & fees
9.2/10 Wonderful! (5,148 reviews)
Great stay. We would def return.

Reviewed on 12 Apr 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 £111 per night from 10 May to 11 May
£111
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (6,645 reviews)
Great location

Reviewed on 12 Apr 2026

Universal's Cabana Bay Beach Resort
See all 38,664 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oakland travel package cost?
The most affordable Oakland travel package is £703, so your dream getaway can become a reality — without burning a hole in your pocket. Bundle flights, hotels, car rentals and more to tailor make a package that fits you.
If I'm not able to travel, can I cancel my Oakland travel package?
Your situation can change in a flash, so yes. You may be able to cancel or alter your Oakland travel package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Need more information? Have a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Oakland?
Track down flights that fit your schedule, add a hotel room to your booking and see how much you save with an Oakland travel package. It's that simple! From flights and hotels to rental cars and activities, Expedia makes travelling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotel options worldwide to select from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Oakland holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply click on the payment plan best suited to your needs during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can escape on that well-earned holiday now.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Oakland?
With lots to discover in Oakland, it makes sense to stay near its attractions. Resurrection Catholic Church, West Orange Trail and Winter Garden Heritage Museum are some fascinating ones to put on your must-see list.
What are the top hotels in Oakland?
If it's your first time in Oakland, lock in a room at The Grove Resort & Water Park Orlando or Liki Tiki Village by Diamond Resorts. Both hotels offer comfortable beds and are top options with lots of travellers.
How far in advance should I book my Oakland holiday?
It can be difficult to know when the best time is to book your Oakland holiday. But usually the earlier you book, the cheaper the prices. Sometimes, you can reserve your flights and hotels nearly 12 months before departure. If you're considering a last-minute getaway, no need to panic! There are incredible deals announced on Expedia all the time.
What does an Expedia Oakland travel package include?
Hotels, flights and a cool set of wheels for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on some tours and activities and watch your savings stack up. When it comes to creating your Oakland escape, you're the one in control!
What should I know before booking an Oakland travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with an Oakland Expedia travel package?
With a travel package, you're in charge. Whether you'd prefer to fly to Oakland in economy or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines all over the world.

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

Surfari Water Park

Enjoy the thrill rides with your children 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 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

£29
per traveller
86% of travellers recommend
LEGOLAND® Florida 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

£20
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Aquatica Orlando

Aquatica Orlando

£40
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. Flight-inclusive packages are ATOL protected.