Villas with a private pool around Cortona and Arezzo
The Val di Chiana is one of the widest views in Tuscany, and around Cortona the best pools are placed to face it. In high summer inland heat makes a pool less a luxury than a necessity, and a house on the hillside, with a breeze and the valley spread out below, is where the long afternoons are spent.
Among the villas on this page, one just below the town has an infinity pool looking out over the valley. A small house beneath the walls has its own pool with Roman steps, useful for children and for easing in slowly. In a country house near Castiglion Fiorentino, a heated indoor pool with water jets sits under a frescoed vault, so swimming continues whatever the season.
At a glance
- 6 private villas
- From 2 to 16 bedrooms
- Up to 32 guests in one villa
- 6 with a private pool
- 2 with a cook or staff
- Availability and price on request, reply within one working day
Wide steps across one end of a pool make it easier for young children and older guests to enter and to sit in the shallows.
Outdoor pools generally close in October. A heated indoor pool allows swimming in spring, autumn and even winter.
Houses on the eastern slopes, below Cortona, look west across the valley: evening light on the water is part of the pleasure.
Choose your villa
Add up to five villas to your list and send one request with your dates: we confirm availability and price with each owner.
Positions are approximate: the exact address is shared once your stay is confirmed.
Questions before you choose
When are outdoor pools open?
From May to October in most villas. If your dates fall at either edge of that period, we will ask whether the pool is heated.
What is the nearest airport?
Perugia is closest, at about 45 minutes. Florence is around an hour and a half, and Rome Fiumicino roughly two and a half hours. A hire car is needed.
Can we ask about several villas together?
Yes, up to five in a single request. Each owner is contacted directly, and you will have our answer on dates and price within one working day.
- Villas with a private pool in Positano
- Villas with a private pool on the Amalfi Coast
- Ravello villas with a private pool
- Praiano villas with a pool over the sea
- Sorrento villas with a private pool
- Villas with a pool in Massa Lubrense and Nerano
- Capri villas with a private pool
- Villas with a private pool on Ischia
- Tuscany villas with a private pool, from hill to sea
- Chianti villas with a private pool above the vines