Family villas in Chianti, with room to roam
Chianti gives children something the coast cannot: space. There are olive groves to run through, white roads for bicycles, and hill towns whose medieval walls can still be walked. Monteriggioni's ring of towers and the skyline of San Gimignano look like a picture book come to life, and Florence and Siena are close enough for a morning visit before the heat.
Every one of the 86 villas below has at least three bedrooms and a pool or family equipment. Near Montaione, independent houses stand among centuries old olive trees with a small lake, a vineyard and a 15 x 8 m pool; two of the three houses below Panzano have heated indoor pools; and the Ghirlandaio family's estate at Impruneta has vineyards, olive groves and a lake of its own.
At a glance
- 86 private villas
- From 3 to 20 bedrooms
- Up to 41 guests in one villa
- 86 with a private pool
- 29 with a cook or staff
- Availability and price on request, reply within one working day
Monteriggioni, between Siena and Florence, is a complete walled village with towers; sections of the ramparts are open to walk and short enough for children.
An evening in a Chianti town square, with gelato and room to run, is the family ritual of summer. Greve's arcaded piazza is a favourite.
Estates of several houses let families keep their own space and bedtimes, then meet at the pool and around one table in the evening.
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 86 villas






























































Positions are approximate: the exact address is shared once your stay is confirmed.
Questions before you choose
Are the villas suitable for young children?
Many are, but historic houses have stairs, uneven floors and pools that may be unfenced. Tell us your children's ages and we will ask each owner about cots, high chairs, gates and pool safety.
Is Chianti too far from the beach?
The nearest Tyrrhenian beaches are around 1 hour 30 minutes away by car, so most families treat the sea as a day trip and let the villa pool do the daily work.
When do school holiday weeks book up?
July and August, Easter and the October half term go first, and in summer these weeks usually run Saturday to Saturday. Send up to five villas in a single enquiry and we reply within one working day.
- 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
- Large villas in Chianti for groups of family and friends
- Chianti villas with a private pool above the vines
- Staffed villas in Chianti, from castles to palazzi
- Family villas in Positano, with pools and sea
- Family villas on the Amalfi Coast
- Family villas in Ravello, with room to roam
- Family villas in Amalfi, among the lemon groves
- Family villas in Sorrento and on the peninsula
- Family villas in Massa Lubrense and Nerano
- Family villas on Capri
- Family villas in Tuscany, between pinewood and sea
- Family villas in the Val d'Orcia, with room for all
- Family villas around Lucca, with room for everyone