What's the best PoD out there for both the Habsburg and Bourbon royal houses (and the countries they control) to become allies, with the condition that it lasts past a single major war? Is such an alliance feasible in the long term?
Would the 18th century be the most likely context for this scenario, considering the rise of Prussia?
 
There are so many possible good PODs that it's hard to make a choice.

One of the most obvious is one where Habsburg Austria would agree to Bourbon France obtaining the spanish/austrian Low Countries and something close to the Rhine frontier and France would agree in exchange for Austria to obtain Bavaria and retain or regain Silesia.

However, you need to avoid France's revolutionary meltdown to have it last.

Concerning the spanish Habsbugs, you had It OTL with the acquisition of most spanish Habsburg holdings by the Bourbons through inheritance : kind of friendly merger/acquisition. And what happened in 1700-1713 could have happened as early as 1665 if Philip IV of Spain had left no surviving son.
 
The easiest way is to find them a common enemy. Most likely in mine idea would be a strong and independent Burgundy and maybe Spain - In Italy France and Austria could find common ground. For the alliance surviving a major conflict: have them not win. As long as the cmmon enemy remains there is a good chance the alliance will last.
 
Impossible without a common threat.
The easiest way is to find them a common enemy. Most likely in mine idea would be a strong and independent Burgundy and maybe Spain - In Italy France and Austria could find common ground. For the alliance surviving a major conflict: have them not win. As long as the common enemy remains there is a good chance the alliance will last.
Prussia seems like the most likely candidate here.
Although, would Britain suffice?
 
Prussia seems like the most likely candidate here.
Although, would Britain suffice?

Prussia is too late on the scene for that I think. Get them stong much earlier and yes.

Britain: Unless it becomes a land power and starts to have some problem with Austria I dont think so.
 
The best PoD is probably keeping the Habsburgs out of Spain. Perhaps give Ferdinand II of Aragon the Not-Philip Son he dreamed of, and have this Son go on to become King of Spain. Or even better, there's Miguel da Paz, who died in infancy but would have had a stronger claim to Spain than Philip and thus The Habsburgs. Have him Survive, and that would give you a United Iberia under the House of Aviz.

In this case, rather than the Habsburgs becoming the 800 Pound Gorilla that unites everyone against them, you wind up with a 4-point diplomatic situation between England, France, Spain, and Austria.

In this situation, the Habsburgs still rule The Netherlands. However France is no longer encircled by the Habsburgs, and thus won't devote every effort to fighting them. This not only keeps the Habsburgs from being the overwhelming Rival of France, but also gives you two other countries who can serve as Common Rivals. Spain and England would make natural allies against France, especially since this Aviz founded Spain would likely maintain the Anglo-Portuguese Alliance. When considering Habsburg Claims to Northern Italy and possible claims to Southern Italy as well, plus potential rivalry with England over Naval Trade, the England-Spain Alliance can serve as a natural Rival to bring together a France-Austria Alliance.

Though really it would probably wind up as a Constantly Shifting Dance, with Allies trading spots and steps constantly.
 
I doubt it would produce the result you mention for the reason that It is what happened OTL.

What was unforeseen was the extinction of the Trastamaras. But the Habsburgs and the Trastamaras OTL concluded crossed marriages in order to balance the superpower that France was in the late 15th century.
 
They allied in 1756 and the alliance survived the Seven Years War, so OTL kind fulfilled OP's demands.
 
In this situation, the Habsburgs still rule The Netherlands. However France is no longer encircled by the Habsburgs, and thus won't devote every effort to fighting them.

But the Low Countries and the Franche-Comté are prime targets for French expansion. I think Habsburg possession of them is actually a bigger obstacle to an alliance than Habsburg rule in Spain. France can tolerate a Habsburg presence on its southern border (far away from Paris) more easily than it can on its northern border.
 
Bourbon - Habsburg Always... A match made in paradise with soup du jour avec du pain at the Rendezvous Cafe... What it lacks in conversation, it makes up for in friendship and amore. Thanks
 
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If I'm not mistaken, the Franche-Comte and much of what became the Spanish Netherlands entered into the Habsburgs possessions through the Burgundian inheritance when Mary of Burgundy married Maximillian. Since her father was the last of the Valois line of Burgundian dukes, if she ends up marrying someone else and thus have all the Burgundian lands pass to someone else, the Valois and Habsburg houses could possibly aid each other in picking off these territories from a common enemy.
 
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