Selling a condo that is booked with a short term rental.

If it I renting it, i wouldn't want someone going into a place that I paid for and had my personal belongings. Now if you put that in the description prior, then the renter at least knows what may happen.

I would say summer is worst time to sell. High season seems better when there are more potential buyers on island. I have seen notices on vacation rental reservation sites that condo is for sale and may require a showing during rental etc. If the renter is told upfront of the possibility of showing then I think that's fine. Otherwise I agree that renters may not be keen on this and don't see that it's all that fair to show it, or at least not without asking if they are OK with it first.

Someone on vacation might get aggravated when potential buyers come around if they weren't warned this could happen when they rented the condo.

We rented for a month out at Coakley Bay a few yrs back with the full knowledge that the condo was for sale and there was the possibility that people could come by to look at it (with prior warning). It didn't bother us, we'd just make plans to head out somewhere on the island during that time. And as a thank you, the realtor left us a gift certificate to Tutto Benes 🙂

I think the fair thing to do is to warn your potential renters and let them decide. That worked for us, the condo was sold and everyone was happy!

I worked for a management company that had several of it's condos for sale and also short term rented them. All of the contracts with the short term renters stated that they were for sale and showings may occur. Occasionally a person would grumble if there was a showing during their stay, but for the most part, it was pretty easy to work around potential buyers and short term renters. Many of the people who viewed the condos were interested in the short term rental potential. So I would think having the place booked would be a benefit in that respect. For any current renters that don't have the 'showing' provision in their contracts I would reach out to them individually and ask them to sign a revised contract. If they refuse, you will at least know when your 'black out' dates are for showing the place. That would be the right thing to do I think, regardless of what your relator told you.

What Julie said is pretty much the norm.
I've seen where showings are blocked out due to vacation rental occupancy but it's unfortunate but if not given the opportunity to view, at the time a potential buyer wishes, they just move on to another unit and may not ever get back to viewing that unit. There's a lot of competition.

It takes very little time to show the interior of a condo unit so as long as your guests are aware the unit is for sale, that there's a slight possibility it will be shown and are given adequate notice, (I prefer to give 48 hr. notice when possible), it should be fine. Remember, most guests are not hanging out inside the condo all day long. They're at the beach, out exploring, taking an excursion, out to lunch, etc.

Good luck.

Thank you so much for your valuable advice.
This forum helped me so much during the two years. I am reading it everyday and I can't express how grateful I am that you are giving your time and knowledge to newcomers.
I enjoy reading everything about the islands and living there.