Tuscany villas for 20 guests

Compare the largest villas in our collection for parties of twenty or more.

9 villas in our Tuscany collection sleep 20 or more, and every one of them has a private pool. 2 list a heated pool. The largest, Dimora Ghirlandaio Estate, sleeps 37. A private chef can be arranged at every villa.

9 villas

Solare del Chianti — the farmhouse among olive groves and vineyards from the air
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Solare del Chianti

Chianti · 20 guests · 10 bedrooms

From €13,500 / week

Spa · Gym

Rooms: 10 bedrooms · 9 bathrooms

Borgo delle Vigne — the estate's three farmhouses
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Borgo delle Vigne

Chianti · 22 guests · 9 bedrooms

From €11,160 / week

Heated pool · Cinema room

Rooms: 9 bedrooms · 9 bathrooms

Borgo Bernardini, a villa in Lucca & Garfagnana, Tuscany
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Borgo Bernardini

Lucca & Garfagnana · 24 guests · 12 bedrooms

From €23,200 / week

Private chef · Wine cellar

Rooms: 12 bedrooms · 12 bathrooms · Fully staffed

Villa Poggio d'Oro — the ochre façade across the lawn, framed by umbrella pines
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Villa Poggio d'Oro

Montalcino · 24 guests · 12 bedrooms

From €30,730 / week

Panoramic view

Rooms: 12 bedrooms · 14 bathrooms

Villa Controni, a villa in Lucca & Garfagnana, Tuscany
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Villa Controni

Lucca & Garfagnana · 24 guests · 12 bedrooms

From €22,000 / week

Private chef · Private chapel

Rooms: 12 bedrooms · 12 bathrooms · Fully staffed

Villa Elle, a villa in Siena, Tuscany
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Villa Elle

Siena · 24 guests · 12 bedrooms

From €13,503 / week

Panoramic view · Pizza oven

Rooms: 12 bedrooms · 12 bathrooms

Tenuta La Barricaia — the stone villa above its infinity pool and garden
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Tenuta La Barricaia

Val d'Orcia · 26 guests · 13 bedrooms

From €22,344 / week

Spa · Infinity pool

Rooms: 13 bedrooms · 13 bathrooms

Tenuta Belvedere Estate: Tenuta Belvedere — the villa above its saltwater pool and lawns
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Tenuta Belvedere Estate

Chianti · 26 guests · 13 bedrooms

From €67,900 / week

Spa · Working vineyard

Rooms: 13 bedrooms · 13 bathrooms · Private chef

Dimora Ghirlandaio Estate — at Dimora Ghirlandaio
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Dimora Ghirlandaio Estate

Dimora Ghirlandaio · 37 guests · 20 bedrooms

From €91,000 / week

Private chef · Spa

Rooms: 20 bedrooms · 17 bathrooms · Fully staffed

Choosing the right villa

Sleeping capacity is only the starting point: check private bedrooms, en-suite bathrooms, shared dining and the layout between buildings. For a reunion, birthday or wedding stay, confirm the arrangements for your specific occasion separately from the accommodation booking.

Compare accommodation for twenty to twenty-four

For twenty guests, Villa Elle and Villa Controni both offer published capacity for twenty-four in twelve bedrooms. Elle spreads the accommodation across three buildings; Controni has twelve en-suite guestrooms and several living rooms. Compare these with Borgo Bernardini, checking its current room layout against your guest list.

This collection answers the capacity question: which villas can accommodate at least twenty? For the wider comparison of separate buildings, en-suites and celebration spaces, use our large-group layout guide. Once a property fits, follow the rental process to confirm dates and terms.

One dining table for twenty or more

For twenty or more, ask for the seating arrangement rather than a description of a spacious dining room. Villa Elle’s published details describe a main-villa table for 26; for every shortlisted property, confirm the indoor and outdoor seating for your exact attendance and enough space for catering staff to serve comfortably.

If twenty residents will be joined by visiting friends, specify both numbers when requesting a birthday celebration. Check permission, suppliers, music and extra charges. A table large enough for dinner is a useful starting point, but does not establish event approval.

A rooming plan for ten couples or mixed households

Ten couples sharing one bedroom per couple need ten suitable bedrooms. A party with single travellers may need more; children sharing may need a different bed configuration. In a twelve-bedroom villa, decide how the additional rooms would be used rather than assuming every room can be converted to twins.

Ask for available floor plans identifying en-suite and shared bathrooms, stairs and the route to the main dining room. For a stay spread across buildings, assign households before booking and confirm that all the accommodation on your plan is included. Use our family gathering advice if several generations have different access needs.

What a villa this size has to prove

Anyone can advertise twenty beds. The questions that matter are whether all twenty are in real bedrooms, whether the bathrooms keep pace, whether the kitchen is professional enough for a brigade, and whether the owner permits the celebration you are planning and what arrangements it requires. Ask for these details in writing for the villa and dates you choose.

For a party larger than one villa can accommodate, ask about combining properties. Confirm availability, actual walking or driving distances and which villa can host shared meals; being on the same estate does not necessarily mean being next door.

Book early, and book the right week

When ten or more bedrooms are essential, enquire before the group books flights. Compare your preferred week with alternative dates and confirm minimum stays, arrival days and which buildings are included. For an October gathering, indoor seating and heating deserve as much attention as the terrace; do not assume an outdoor meal will be possible every evening.

Frequently asked

Which villas in Tuscany sleep 20 with a private pool?
9 villas in our collection sleep 20 or more and have a private pool: Solare del Chianti, Borgo delle Vigne, Borgo Bernardini, Villa Controni, Villa Poggio d'Oro, Villa Elle, Tenuta La Barricaia, Tenuta Belvedere Estate and Dimora Ghirlandaio Estate. Tell us your dates and we will confirm which are free.
Can twenty guests stay in a villa that sleeps twenty-four?
Yes, subject to the villa’s booking terms. Confirm that the quote includes the bedrooms and buildings you intend to use. The extra capacity may help with single travellers or a more flexible rooming plan; it does not necessarily reduce the whole-property rental rate.
How much does a villa for 20 cost?
Use the weekly rate for the villa and dates you want, with an itemised list of inclusions and extras. For illustration, €30,000 divided among twenty paying guests is €1,500 each before separately charged services. Catering and event arrangements must be checked against the actual quote.
Are these villas licensed for weddings?
Wedding arrangements are property-specific. Confirm the type of ceremony, permitted event numbers and overnight capacity separately; a villa sleeping twenty does not automatically permit a twenty-person event or a legal ceremony.

See also

Tell us the dates, the numbers and what the week is for. , usually within a working day.