Hello @Michael402
You have a lovely condo with great facilities in the club-house!
Am I right in understanding that you are living in the condo just part of the time? To maximise the letting potential I understand you want to let one room while you're living there, and when you're away, you want to let the two rooms separately to separate guests. Do you also want to let the whole condo at times? Or have I got this wrong!
That would mean setting up 3 listings:
1) (when you're there) a Private Room in an apartment, with a Private Bathroom, and kitchen (and say that the kitchen is shared with the owner when you're there, and with another guest when you aren't there)
2) (when you're away) a whole Apartment with 2 bedrooms, 2 bathrooms and kitchen
3) (when you're way) (for your second bedroom) a Private Room in an apartment with a Private Bathroom and say that the kitchen and common areas like the sitting room are shared with another guest.
I have to say that listing 3) is unusual, but in fact not so different from apartments I have stayed in where I've shared the kitchen with another guest, when the host lives in the apartment, but hardly ever appears. I would have thought you could charge more letting the whole condo when you're away, than letting to two separate people with a shared kitchen and sitting-room.
For three listings, you would have three calendars, and you would have to be scrupulously careful to update each one as you got bookings for another one. Personally, I would find this a nightmare!
Whichever arrangement you choose, it is dependent on your knowing exactly when you're going to be away, and blocking the other calendar(s) on the corresponding dates. If you can't plan very far ahead, you can set your listing to block future dates.
I think you would be well advised just to have two listings and let a Private Room when you're there, and the Whole Apartment when you're away (or if you are still keen on letting two rooms to two separate people, just use listing suggestions 1) and 3) Always let guests know if you're going to be there yourself.
I like your photos; I think some of them just need labels to say whether they are part of the club house or in your apartment (eg photo no. 5 and 9). You should also have a photo of the second bedroom in the appropriate listing. A brighter photo would be better, with fewer items, and straighten the bed covers and curtains! (I always judge a room on the tidiness of a bed - if the host takes trouble with the bed covers, I get the impression they will take care of other details - just me being fussy!)
You have a fabulous property with great assets, and the money should soon be rolling in! Good luck!
