The tourist season is commonly June, July and August in Spain. Until mid September prices of housing will be ridiculous and inventory will be low to non-existent. In major cities one can add student activity to that. So move mid September or later but not much later. Landlords here tend to think short term, so it is of no use planning long term in Spain. Beginning of September they will start getting nervous about new renters, especially if they see more inventory appearing, so more competition.
So that is the best time to start looking. Do not wait too long though or the inventory will dry up again or it will simply be taken off the market by owners getting tired of seeing prospective renters and who already made lots of money in the usual summer months and do not really need the annual income.
In coastal areas this is especially a dominant symptom, since there at least 80% of homes is occupied by outsiders.
Also take into account a very unusual aspect of the housing market that is typical for Spain and maybe a little for Portiugal as well. Many baby boomers have inherited homes they do not need and will not do any or barely maintenance on and that also do not suit their needs as they have bad locations for them (not in or near major city) ancient lay out, built for large families which do not exist anymore, constructed poorly etc). This is why there is a huge inventory of 1 million empty unused homes in Spain n top of that comes the emotionalism of many Spaniards that they heavily overvalue the value of their homes, so ask way too high a purchase price (often 2-3 times its real value) or rental price. Many will not budge on that until they get financially in trouble with teh house or never, so they let thr house decay. rental protection has dimineshed in favor of owners but it is still ridiculously costly (at least EUR 700 and a many months of wait time for a court decision which can get worse if courts are on strike for months like now in Galicia.
The realty industry, so the brokers are not regulated, which is good, but it also lead here to often poor quality of service because of ignorance and poor sales skills. realtors and brokers are mostly not qualified to help you with a rental (or sale or purchase) as they like to only provide services for overpriced A1 location objects, not affordable stuff. So look for direct dealing with the owner instead.
This means you really need to be well versed in Spanish and in the quirks of the rental market. In my opinion there is a huge market for brokers who offer a service for a fee here but those do not exist in most places.
One matter that I caution you about is the deposit. Insist on having the contract and deposit registered with the local authorities and do not pay more than 1 month as that is all those will cover. It has as a consequence that they can come after you for the renters tax they now started charging, but they may not. Of course, if your have no contract registered there is usually no such tax. see it as an insurance though.
Never accept any deals where more than 1 month deposit is required. It is a set up for trouble. Never also sign any deal unless all is fixed that needs fixing as the landlord will disappear and not fix most things once the contract is signed. If he promised to put in a furnace, insist it gets put in first before you sign and move in. Otherwise it is just a trick to have you finance what he cannot afford. You're not a bank though and you would be running all the risk.
If an owner lives very far away from your rental, do not sign. That is a set up for no services at all with issues with the house, no fixes. Do not believe in any stories of the landlord 'having someone to take care of things'.
As to jobs, there are no jobs for foreigners in Spain beyond seasonally teaching English and that often at ridiculously low hourly rates. Here in Spain a language teacher with a university degree tutoring privately will often not charge more than EUR 6-8 an hour! At bets you can earn EUR 10 teaching a whole class and it won't be regular large volume work. It is no surprise that most Spanish kids are leaving the country and leaving it mainly to pensioners. That is a demographic trend.
All you could try is service foreign pensioners here, but then you would need to go live in areas where they abound. That may be a growing market. Take into account though that the Spanish are getting more and more difficult for foreigners, especially taxing them and demanding more paper work, so many pensioners have already left. The foreign wealthy are now also being chased away, while they are far more welcome across the border in Portugal.
Setting up a business here is also only for the very happy few who are so foolish.
This is mainly a place for old pensioners like me,
Festivals abound in summer and late spring, even autumn, but in many areas it is largely for the young. Only in very touristy areas it will still have the Spanish flavor instead of loud modern music and loud fireworks.
In Galicia I would recommend then especially fish related festivals where one can inexpensively taste the local fish. The music is not great there though. In Andalucia one will find ten times better but that is no wonder with so many foreign tourists there and a far better financial situation of its inhabitants.
The richer the towns and cities, the better celebrations.
Of course the real flavor is not just in festivals and fiestas. One can find it in local bars and restaurants mainly frequented by Spaniards not tourists or on beaches mainly Spanish visit. The thing is that the younger generation is not very 'Spanish' anymore.
Of course there is no denying that the siesta and Sunday shop closures are typically Spanish. ;-)
Your bets bet is in talking to neighbors, shopkeepers, drivers etc.. They are Spain and often love talking A LOT! Especially in more rural areas where people take their time and little is urgent. Be prepared that politics and religion are hot and main issues on all levels.
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