Travel Guide · For Families
Large Family Villas in Tuscany with a Pool for 14 People
The best areas for a family reunion of 14, from Chianti to Lucca, and the villas with the pool, the bedrooms and the long table to match.
The best large family villas in Tuscany with a pool for 14 people are in four areas: Chianti, between Florence and Siena; the hills around Lucca; the countryside south of Siena and the Val d’Orcia; and Cortona. Villas that sleep 14 usually have seven bedrooms, and the best ones for a family reunion add a fenced or covered pool, a long outdoor table and a chef on call. Doorways Villa Vacations, an Italian villa specialist since 1994, has personally inspected every villa in this guide.
A family reunion of 14 is the trip we plan most often: grandparents, two or three grown children, their partners and a crowd of cousins. Here is how to choose the area, and the villas we would book.
What are the best areas in Tuscany for a family villa for 14?
Chianti, for wine and day trips to Florence and Siena
Chianti sits between Florence and Siena, so both cities are within an hour, and the vineyards and stone villages are on your doorstep. It is our first suggestion for families who want a little of everything.
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Colli Chianti |
7 / 14 | From €19,895 / week From about €203 per person a night, €1,421 a week (14 guests, 7-night minimum) |
An infinity pool with a remote-controlled safety cover, a pizza oven and an outdoor cinema |
| Villa Amarika Chianti |
7 / 14 | From €30,560 / week From about €312 per person a night, €2,183 a week (14 guests, 7-night minimum) |
A restored 1684 estate near Castellina, with an owner who loves to spoil her guests |
| Villa Trionfante Chianti |
7 / 14 | From €28,570 / week From about €292 per person a night, €2,041 a week (14 guests, 7-night minimum) |
At the end of a half-mile lane, with private river access and two pizza ovens |
| Villa Chiara Chianti |
8 / 16 | From €11,460 / week From about €102 per person a night, €716 a week (16 guests, 7-night minimum) |
An infinity pool and a spa, halfway between Florence and Siena |
| Casa Bachicche Chianti |
8 / 16 | From €19,200 / week From about €171 per person a night, €1,200 a week (16 guests, 7-night minimum) |
A heated pool and private spa, fifteen minutes from Florence |
| Villa Tavernaccia Chianti |
8 / 16 | From €32,000 / week From about €286 per person a night, €2,000 a week (16 guests, 7-night minimum) |
A Renaissance villa with an open-air theater and a view of Florence's dome |
Lucca, for an easy pace and a chef at home
The hills around Lucca are gentle and green, the walled city is ten minutes away for bike rides on the ramparts, and the beaches of the Versilia coast are close for a day by the sea. These three villas on the Coselli Estate each come with a chef six days a week.
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Lenka Lucca |
7 / 14 | From €14,995 / week From about €153 per person a night, €1,071 a week (14 guests, 7-night minimum) |
A 1624 country house with a pool framed by cypresses and lemon trees |
| Casa Felice Matteucci Lucca |
7 / 14 | From €11,995 / week From about €122 per person a night, €857 a week (14 guests, 7-night minimum) |
A floodlit pool and a private lake, with tennis on the estate |
| Casa Del Fattore Lucca |
8 / 15 | From €14,995 / week From about €143 per person a night, €1,000 a week (15 guests, 7-night minimum) |
A chef and a waiter six days a week, in the village of Vorno |
South of Siena and the Val d’Orcia, for the postcard views
South of Siena, the Crete Senesi and the Val d’Orcia are the rolling hills and cypress roads you have seen in every photograph of Tuscany. Expect more space, quieter roads and longer drives into town.
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Cardinale Siena |
8 / 16 | From €32,000 / week From about €286 per person a night, €2,000 a week (16 guests, 7-night minimum) |
A historic house on a working wine and olive oil estate near Buonconvento |
| Villa Benessere Siena |
10 / 20 | From €21,191 / week From about €151 per person a night, €1,060 a week (20 guests, 7-night minimum) |
Room to spread out, with a wellness annex, tennis and bocce near Sarteano |
Cortona, for walking into town
If your family wants to walk to dinner, Cortona is the answer: two of our villas here are a stroll from the hill town’s piazza. Both sleep more than 14, so there is room for a few extra guests.
| Villa | Bedrooms / sleeps | Rate | Why we chose it |
|---|---|---|---|
| Villa Ivana Cortona |
9 / 18 | From €10,150 / week From about €81 per person a night, €564 a week (18 guests, 7-night minimum) |
Its own restored chapel, walking distance to Cortona |
| Villa Laura Cortona |
10 / 20 | From €25,000 / week From about €179 per person a night, €1,250 a week (20 guests, 7-night minimum) |
Bramasole, the villa from Under the Tuscan Sun |
What should a family villa for 14 have?
- Seven bedrooms with their own bathrooms, or as close as possible, so mornings run smoothly.
- A safe pool for the youngest swimmers: a fence, a safety cover or a shallow end. Ask us which villas have one.
- A ground-floor bedroom for grandparents. See our Tuscany villas with ground-floor bedrooms and fewer stairs.
- One table for everyone, indoors and out, and a kitchen big enough for two cooks.
- A chef on call, at least for a welcome dinner and the big celebration night.
How much does a villa for 14 in Tuscany cost?
The live tables above show each villa’s starting weekly rate, updated from our listings. Split between four or five families, a week in a large villa often costs less per person than hotel rooms, with far more space and privacy. Rates are highest in July and August; June and September offer the best balance of weather and value.
When should you book a family reunion villa?
Book 9 to 12 months ahead for June, July, August and September, when the largest villas go first. Spring and fall leave more choice. Our guide to the best time to visit Siena and our best time to visit Lucca cover the seasons.
Plan your family reunion with us
Tell us who is coming, the ages of the children and what everyone loves, and we will suggest two or three villas that fit, with notes on bedrooms, stairs and the pool. Talk to a Doorways advisor, or see more ideas in large villas in Chianti and Siena for 16 or more and where to stay in Siena.
Frequently asked questions
Where is the best place in Tuscany to rent a villa for 14 people?
Chianti, between Florence and Siena, is our first choice for most families because both cities are within an hour. The hills around Lucca are gentler and closer to the sea, and the countryside south of Siena and the Val d'Orcia has the most famous views.
How many bedrooms do you need for 14 people?
Usually seven, with a bathroom for each if possible. Families with young children can sometimes manage with six by sharing rooms.
Can you get a private chef at a villa in Tuscany?
Yes. Several of our villas for 14 include a chef, like the Coselli Estate villas near Lucca, and most others can arrange one for dinners or a cooking class.
How far ahead should you book a villa for a family reunion?
Nine to 12 months ahead for June to September, when the largest villas are the first to go.
