The hottest place is Portugal in May is Évora (24ºC) in the beautiful Alentejo region between Lisbon and the Algarve. Both Lisbon (22ºC) and Faro (22ºC) on the Algarve coast will feel warm in May, with temperatures likely to reach the high 20s.
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The warmest part of the Algarve is the eastern Algarve. The more west you travel, the colder and windier it usually gets, especially ones you go around the corner at Sagres. I would recommend staying anywhere in between the Spanish boarder and Salema.
Albufeira is a coastal town in the Algarve region of southern Portugal. It is located about 40 km north of the city of Faro. Albufeira is one of the warmest places in Portugal in winter because of its perfect climate.
This one is a close call with both destinations seeing temperatures sitting in the balmy mid- to late-twenties during the summer months. Out of the peak season, the Greek island of Crete warms up as early as May hitting around 25C, while the Algarve isn't far behind at around 22C.
The best month to visit Portugal, specifically the Algarve, is during the shoulder season. I personally love visiting in May-June or late Sept-October. If you're looking to make the most of the Algarve, the sweet spot lies in the shoulder season — May-June and September-October.
It's balmier and drier as you move further south to Lisbon, where highs around this time can reach 72°F (22°C). Beach days get likelier in May as temperatures in the Algarve, in Portugal's south, hit up to 72°F (25°C).
What are the hottest places in Europe in May? The hottest city in Europe in May is Seville (27°C) in southern Spain, followed by Antalya (26°C) in southern Turkey. The islands of Crete, Malta and Cyprus will also feel hot at 24°C, along with Valencia and the Costa de la Luz (24°C) in Spain.
How Often Does It Rain in May? During May, Lisbon will feature about 17 mostly sunny, 4 partly sunny, and about 10 mostly cloudy days. You can also expect that 9-10 days will record some rainfall. However, only about 5 days record at least 1 mm (0.04 inches) or more, and only 2 days will see 10 mm (0.4 inches) or more.
Summarizing: The weather in May is reliable and warm with average temperatures around 22-24 degrees. Make sure to bring good sunscreen and clothes for warm day temperatures and slightly colder evenings.
Not much difference in average temps in either location, though the algarve is more influenced by its proximity to atlantic weather systems than the costa del sols more sheltered med location.