Chianti villas with a private pool above the vines
Inland Chianti is hotter in summer than the coast, which is why the pool matters here more than almost anywhere in Tuscany. A pool on a Chianti hillside is also a viewpoint: rows of vines falling away below, a village on the next ridge, the evening light catching the cypresses. It is where the day begins with a swim and ends with a glass of wine.
Every one of the 92 villas below has a pool of its own. Above Figline Valdarno, a 16th century ducal estate has a main pool looking over vineyards, cypress woods and the distant Apennines; a 14th century watchtower above Poggibonsi pairs a 16 x 8 m pool with rose gardens and a travertine staircase; and two of three restored houses below Panzano have heated indoor pools for the cooler months.
At a glance
- 92 private villas
- From 2 to 20 bedrooms
- Up to 41 guests in one villa
- 92 with a private pool
- 32 with a cook or staff
- Availability and price on request, reply within one working day
Heated indoor pools, rare in the countryside, make swimming possible at Easter or in November, when outdoor pools are covered.
For a large party, ask how many sun loungers and umbrellas there are, and whether a pergola or trees shade part of the pool terrace.
After a day in Florence or Siena, the pool at dusk is often the best swim of the day, with the stone still warm underfoot.
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.
Show all 92 villas
Positions are approximate: the exact address is shared once your stay is confirmed.
Questions before you choose
When are villa pools open in Chianti?
Outdoor pools usually open in May and close in October, sometimes earlier if the weather turns. The water is at its most pleasant from mid June to mid September.
Can the pool be heated in spring or autumn?
Some owners offer heating, usually for an extra charge, and it helps most in May and early October. We ask about heating and its cost when we check your dates.
Do villas rent by the week?
In high season, generally Saturday to Saturday. Outside July and August some owners accept shorter stays. Choose up to five villas in one request and we reply within one working day with the options.
- Summer in Chianti from a villa among the vines
- Easter in Chianti, in a villa of your own
- Autumn in Chianti, a villa for the harvest
- Christmas in Chianti, by the fire in your own villa
- Wedding villas in Chianti among vineyards and olives
- Family villas in Chianti, with room to roam
- Large villas in Chianti for groups of family and friends
- Staffed villas in Chianti, from castles to palazzi
- 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
- Val d'Orcia villas with a pool facing the hills