We stayed at the smaller of the two trulli, Sopra, in mid September. The property is very pretty, well equipped and it is clear the owner puts in an effort to make it so. We stayed as a couple so had loads of space but both bedrooms are ensuite which would work well for a family or two couples. Internally perhaps the most obvious thing lacking is a proper living room- there is basically a space between the two bedrooms set aside for this, beyond the very attractive kitchen/dining area, but we didn't use it as such. That said, you are much more likely to be 'living outdoors' and these spaces were excellent, a large shaded area around the pool, a really delightful shaded lounge and dining area just outside the kitchen door and a table and chairs out the front which we sometimes used for a 'sunshine breakfast'. In September it is dark by 7pm and for a few days didn't use the outside lounge/dining area in the evening but once we discovered how good the outside lighting was, including some nice and atmosheric touches illuminating some nearby trees, we found it a great option for dinner.
The trullo is quite isolated, some way from the nearest village (i.e not realistic walking distance) and therefore very quiet but the price for that was quite a lengthy drive up a very bumpy, unpaved road. On balance we found that well worthwhile for the tranquility, but it does add some time to getting in and out the property.
There is plenty to see and do locally; the sea is less than half an hour away, you are in trulli country so lots of nice towns nearby and even medieval Lecce is not much more than an hour away. We did some sightseeing but less than usual, because we found the trullo such a lovely place to be around during the day, relaxing, reading and cooling off in the pool. I'd recommend arranging a visit to the olive oil producer through Angelita, who looks after the property for the owner- she actually works there and gave a great insight into how virgin oilve oil is produced. The tour is free but you can buy a bottle or two at the end. Angelita is also very helpful in dealing with any minor issue you may have during your stay.
You are in food country here, so no shortage of restaurants; Cortiletto in Speziale (about 20 mins drive) was especially good, very reasonably priced and suggested by the owner. Best supermarket is Famiglia in Osuni- about 20-25 mins drive but we thought worth it for the choice and quality. All in all a very relaxing stay.