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Date one went well, rapport was built, two-way attraction was apparent. After dinner, she asked what shall we do and I suggested that we could get a room to hang out in and just relax.
Edit: misread, didn't realize you were renting it out.
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It seemed like she was down for that idea, but said "Hmmm... it's our first date, I wouldn't feel comfortable doing that,"
Humans (not only women) are wired to process emotions before it reaches the rational part of the brain, if you get her turned on she will have a MUCH harder time saying "no", which is why escalate in a safe environment and slowly break down her barriers.
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to which I acted unneedy and responded "Alright, no worries." Soon we took a walk and joked around a bit more, and near the end when we were about to part, she is the one who went in for the goodbye kiss and held it for a few seconds.
good job, though i still think you should be the one to initiate the moves. you want to lead.
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After that, she explicitly told me through text that she enjoyed kissing me and finds me very attractive. To me, it seems like pretty much a done deal. Any advice on how I should steer date two to get a guaranteed escalation to sex?
well done, and read the above. she knows you want sex, so she may hold out till the 2nd or 3rd date, but if she keeps seeing you knowing this take it as a sign that she also wants it.