In reply to pebbles:
Hey Pebbles.
Have stayed in two places myself, but have had partners that were staying in different places, so have gone to theirs to pick them up, have drinks, etc.
Personally I would still recommend the Hotel Philoxenia as the best place I've seen.
Location wise it's great because it is right underneath the Grande Grotta, so you don't have an epic walk at the start of each day.
The rooms are spacious and have the best views on the island. Plus the guy who runs it (Nicholas) is on site 24 hours a day, has perfect English and is computer savvy, so he can respond to all your needs, at all times - which you can not say about most of the people/places on the island.
No offence to the Greeks; I love the fact that Kalymnos is very unspoilt and old-fashioned, but the reality is a lot of the locals don't have a website, might not speak much English, and would not be at the end of a mobile phone. Which is fine if you're lazing on a beach all day, but when you have a busy week of climbing ahead of you and every hour counts, you don't want to spend a lot of time waiting around because your shower broke and you have to ask the guy from local shop to try and find your landlord, who is his cousin's brother's wife's boss!
Word from the wise - Neil Gresham stays at the Hotel Philoxenia every year and had his 40th birthday party there, so ........ pretty good advert right there.
I've been to Kaly three times now and am just planning my fourth trip, so anything else you need to know, feel free to ask.