We loved the condo. Our daily routine was to make breakfast, walk down the hill to one of the local coffee shops and then walk around the beaches until it started to get really hot. We relied on Uber and Lyft for most of our travels and only rented a car for our last few days on the island. Most of our activities were centered around Wailea, so the location was great.
There were a lot of extremely helpful supplies in the unit, especially 4 sets of beach chairs with backpack-style shoulder straps, a beach umbrella (make sure to screw it in deeply to fight against wind at the beach), a small cooler and an insulated tote bag. The rest of the standard items that you'd expect were also there. The unit was clean but it's definitely a struggle trying to keep floors the same way. We'd pretty religiously rinse off feet and remove shoes at the door but it still somehow got in. We didn't go to the complex's pool at all but it looked pretty nice and was deserted in the mornings.
There's plenty to do around Wailea but we'd also recommend some of things that we did outside of it. Kayaking & snorkeling in Olowalu, hiking around Īao Valley State Monument and hanging out in Paia for a few hours. We would also highly recommend Makena Beach, which is a short car ride South of Wailea. It was postcard beautiful and not crowded at all; although be warned that the surf breaks hard and the current is strong.