Hi we stayed in Pienza in Southern Tuscany, but they have a sister property with a pool, we loved staying at La Bandita townhouse, they are very good with kids, I think meals etc are free and good room rates if you go outside of holiday time, so much to do just walking around, gorgeous countryside, winery visits and swimming in hot springs pools etc. You do need a car, I wrote a post about this on my blog if you want to read a bit more about it, we loved it, but we were coming from Dubai ! Weather would be good then was a bit hot in August.
It's written up as an Eid break as that's a big holiday coming up here.
The Greek islands are lovely from mid-May (we've been in early May and the weather can be a little more varied, although it's still warm). If you want some where child friendly, but not too touristy, maybe Skiathos or Kefalonia would be good. I tend to book just after Christmas, but it's worth looking now to see what's available.
We stayed in a resort called Armacao de Pera in Portugal a couple of years back, flights v reasonable through easy jet, transfers through resorthoppa, accommodation through owners direct , which comes with a booking guarantee, town itself and beach lovely, lots of Portuguese families holiday there and not too Anglo centric. We went end of July for less than 900quid for the three of us!
It's been a while since I booked a holiday (5+ yrs), and I want to go somewhere sunny next spring with dh and the kids (they'll be 3 and 8 mo). We'll be pretty flexible with dates (dh is self employed) and we can avoid school holidays. But to get the best prices should I be looking now, or trying for last minute? Is it best to try and get a package deal or do the budget airlines + accommodation separately? We'd be looking for self-catering, hopefully with a pool, reasonably nice accommodation as we'll be back each afternoon for naps, but preferably not too too touristy. Was thinking portugal, or greek isles, or spanish isles but not too bothered really. We've been living in the tropics for the last 5 yrs so I think by spring time we'll be in need of some sun! Any suggestions of places/companies etc?