I think to have a good holiday you have to throw the idea of what you 'should' do on holiday out the window. At the very early planning stage consider what you want out of it and how you're going to achieve it. You don't have to stay in a hotel next the beach etc.
We like a bit of exploring the area, sun, swimming, chilling/ reading and a few drinks in the evening.
Like to take life slowly everything at our own pace. We like long lie ins & DS is a pretty good sleeper, but does need early nights. Spending half the morning sitting in bed drinking tea and reading is bliss.
We have one DS 4. He doesn't like sand or sitting in restaurants. Loves swimming and playing with other kids. Is very happy playing on his ipad or with lego etc his own for an hour or so.
So we go self catering in a mobile home, with a big pool complex, kids club. We eat lots of bread, cheese & olives type meals. Or cook a pizza or other simple stuff. We had a gas BBQ this year was was brilliant so ate lots of sausages! We're not big foodies and keep food simple. Rocky beaches nearby are perfect. Might pop to a bar for a cocktail in the evening or occasional meal out. But mostly happy sitting outside on veranda drinking wine, playing card or board games and reading while DS is asleep in bed.
The idea of all sharing a room would be no fun for us! Neither would I be prepared to sleep on a sofa bed in the lounge. Need our own bedrooms so at least a 2 bedroom place and some space like a lounge and veranda to be able to sit and chat in the evening without worrying about disturbing DS. Which pretty much rules out hotels as suiting us!
Having to get dressed and go downstairs and sit in a restaurant together for every meal doesn't sound like any fun. Grabbing a bowl of cereal whenever fancy in the morning is fine. Then DS usually eats dinner at about 5 whereas we prefer to eat about 8. Eating together can be pretty stressful if we're all hot and tired. I'd much rather chuck some fish fingers in the oven or do some pesto pasta and wash up a couple of plates than drag the boy to a restaurant when he'd rather go to bed. It's fine a couple of times a week, but 3 times a day no thanks!
I'd certainly need a way to make a cuppa to drink in bed in the morning and a fridge to keep my wine and bars of chocolate cold so a kitchen is essential.
We all have to comprise in some ways, I think it's just about finding what works for you to get what you want out the holiday without the stress!