Oakland Holidays from £865

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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.
Stayable Davenport

Stayable Davenport

2 out of 5
Price was £1,205, price is now £865 per person
£865
per person
30 Jul - 6 Aug
found 1 day ago
Return flight included
Manchester (MAN) to Orlando (MCO)
5.4/10 (36 reviews)
It was a cool stay I’ll book again

Reviewed on 16 Jun 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 £2,257, price is now £1,476 per person
£1,476
per person
26 Aug - 2 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Es excelente este hotel, me encantó su limpieza,atención y muy buena ubicación lo volvería a repetir

Reviewed on 23 Jun 2026

Mission to Mars

Mission to Mars

4 out of 5
Loughman
Save 100% on your flight
Price was £8,386, price is now £5,554 per person
£5,554
per person
5 Sept - 11 Sept
found 15 hours ago
Return flight included
London (LHR) to Orlando (MCO)
No reviews
The Alfond Inn

The Alfond Inn

4 out of 5
Price was £4,487, price is now £3,087 per person
£3,087
per person
1 Aug - 8 Aug
found 3 hours ago
Return direct flight included
London (LON) to Orlando (MCO)
9.6/10 Exceptional! (1,012 reviews)
Loved the location. My room was very comfortable.

Reviewed on 24 Jun 2026

The Vietta Hotel

The Vietta Hotel

2 out of 5
Price was £1,232, price is now £885 per person
£885
per person
30 Jul - 6 Aug
found 1 day ago
Return flight included
Manchester (MAN) to Orlando (MCO)
7.6/10 Good! (1,000 reviews)
El desayuno debe ser algo mas variado

Reviewed on 22 Jun 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 £126 per night from 17 Jul to 18 Jul
£126
17 Jul - 18 Jul
includes taxes & fees
9.2/10 Wonderful! (5,895 reviews)
"I have convinced my husband that we need to come once a year! He is a homebody and hates to travel but somehow he loved the amenities and convenience of our two bedroom villa that we extended out stay. We were pleasantly surprised that a chic fila, Wendy’s, McDonald’s, gas station and Walgreens were ..."

Reviewed on 26 Jun 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 £219 per night from 27 Jul to 28 Jul
£219
27 Jul - 28 Jul
includes taxes & fees
8/10 Very good! (10,235 reviews)
"Loved this property"

Reviewed on 25 Jun 2026

The Grove Resort & Water Park 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 £128 per night from 1 Jul to 2 Jul
£128
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (7,038 reviews)
"I"

Reviewed on 26 Jun 2026

Universal's Cabana Bay Beach Resort
See all 38,809 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 £865, 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.

Things to do

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

£29
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

£450
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Aquatica Orlando

Aquatica Orlando

£39
per traveller
86% 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.