Historic Estate01
Villa San BartolomeoMontepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Spa · Infinity pool
Rooms: 6 bedrooms · 6 bathrooms
VillasLarge groups
Large villas in Tuscany.
Compare large villas to rent in Tuscany for twelve or more guests, including villas sleeping more than sixteen. Start with guest numbers, bedrooms and rates, then ask for floor plans, en-suite details and spaces where everyone can gather.
23 villas for larger parties
The whole collection23 villas
Historic Estate02
Villa LenkaLucca & Garfagnana · 14 guests · 7 bedrooms
From €15,000 / week
Private chef · Frescoed interiors
Rooms: 7 bedrooms · 7 bathrooms · Fully staffed
Countryside Classic03
Villa AgrestoCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Spa · Heated pool
Rooms: 6 bedrooms · 6 bathrooms
Countryside Classic04
Casa dell'ErtaChianti · 14 guests · 7 bedrooms
From €7,810 / week
Spa · Infinity pool
Rooms: 7 bedrooms · 7 bathrooms
Countryside Classic05
Villa MatteucciLucca & Garfagnana · 14 guests · 7 bedrooms
From €12,000 / week
Private chef · Olive grove
Rooms: 7 bedrooms · 7 bathrooms · Fully staffed
Historic Estate06
Casale di Sant'AndreaCortona · 12 guests · 7 bedrooms
From €20,700 / week
Infinity pool · Heated pool
Rooms: 7 bedrooms · 6 bathrooms · Private chef
Countryside Classic07
Villa del FattoreLucca & Garfagnana · 15 guests · 8 bedrooms
From €15,000 / week
Frescoed interiors · Olive grove
Rooms: 8 bedrooms · 8 bathrooms · Private chef
Historic Estate08
Villa CastellaroChianti · 13 guests · 7 bedrooms
From €8,500 / week
Heated pool · Wine cellar
Rooms: 7 bedrooms · 7 bathrooms · Private chef
Countryside Classic09
Villa OddiCastiglion del Bosco · 12 guests · 6 bedrooms
From €91,000 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Tennis court
Rooms: 6 bedrooms · 6 bathrooms
Contemporary Masterwork10
Villa FarfallaLucca & Garfagnana · 14 guests · 6 bedrooms
From €19,000 / week
Panoramic view · Olive grove
Rooms: 6 bedrooms · 6 bathrooms · Private chef
Historic Estate11
Villa della CappellaCortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
Rooms: 9 bedrooms · 10 bathrooms
Historic Estate12
Casale GherardiChianti · 18 guests · 9 bedrooms
From €20,300 / week
Infinity pool · Working vineyard
Rooms: 9 bedrooms · 9 bathrooms
Historic Estate13
Argentaia EstateMaremma · 18 guests · 9 bedrooms
Price on enquiry
Private chef · Spa
Rooms: 9 bedrooms · 10 bathrooms · Fully staffed
Historic Estate14
Villa ErbavoglioChianti · 18 guests · 9 bedrooms
From €17,400 / week
Working vineyard · Olive grove
Rooms: 9 bedrooms · 9 bathrooms
Wellness Estate15
Villa Il CelleseChianti · 19 guests · 10 bedrooms
From €59,500 / week
Spa · Heated pool
Rooms: 10 bedrooms · 11 bathrooms · Private chef
Historic Estate16
Borgo delle VigneChianti · 22 guests · 9 bedrooms
From €11,160 / week
Heated pool · Cinema room
Rooms: 9 bedrooms · 9 bathrooms
Countryside Classic17
Villa ElleSiena · 24 guests · 12 bedrooms
From €13,503 / week
Panoramic view · Pizza oven
Rooms: 12 bedrooms · 12 bathrooms
Restored Borgo18
Borgo BernardiniLucca & Garfagnana · 24 guests · 12 bedrooms
From €23,200 / week
Private chef · Wine cellar
Rooms: 12 bedrooms · 12 bathrooms · Fully staffed
Historic Estate19
Villa Poggio d'OroMontalcino · 24 guests · 12 bedrooms
From €30,730 / week
Panoramic view
Rooms: 12 bedrooms · 14 bathrooms
Historic Estate20
Villa ControniLucca & Garfagnana · 24 guests · 12 bedrooms
From €22,000 / week
Private chef · Private chapel
Rooms: 12 bedrooms · 12 bathrooms · Fully staffed
Wellness Estate21
Tenuta Belvedere EstateChianti · 26 guests · 13 bedrooms
From €67,900 / week
Spa · Working vineyard
Rooms: 13 bedrooms · 13 bathrooms · Private chef
Wellness Estate22
Tenuta La BarricaiaVal d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Spa · Infinity pool
Rooms: 13 bedrooms · 13 bathrooms
Historic Estate23
Dimora Ghirlandaio EstateDimora Ghirlandaio · 37 guests · 20 bedrooms
From €91,000 / week
Private chef · Spa
Rooms: 20 bedrooms · 17 bathrooms · Fully staffed
Compare layouts for a large-group stay
Villa Elle and Villa della Cappella are two of our best sellers for gatherings. Compare them with Villa Controni below: a larger capacity does not necessarily mean the layout is better for your party.
Villa Elle
Siena · Sleeps 24 · 12 bedrooms
- Layout and gathering spaces
- Accommodation across three buildings, with a main-villa dining table described for 26.
- Why consider it?
- Compare for families who want separate sleeping areas and a shared place for meals.
- Before you book
- Request the room allocation across all three buildings, the en-suite breakdown and the routes between bedrooms and dining spaces.
Villa della Cappella
Cortona · Sleeps 18 · 9 bedrooms
- Layout and gathering spaces
- Nine bedrooms with en-suite bathrooms on the upper floors, a grand salon and a games room.
- Why consider it?
- Compare for a group of 16–18 that wants bedrooms and shared rooms within one villa.
- Before you book
- Check stairs against your guests’ needs, indoor dining capacity and permission for the celebration you have in mind.
Villa Controni
Lucca & Garfagnana · Sleeps 24 · 12 bedrooms
- Layout and gathering spaces
- Twelve en-suite bedrooms, three living rooms, a banquet hall and a shaded dining loggia.
- Why consider it?
- Compare for a larger party wanting several indoor spaces and a base around Lucca.
- Before you book
- Confirm seating for your whole party, bedroom access and the arrangements for catering or visiting guests.
Request available floor plans and a bedroom-by-bedroom bathroom list. A dining room, chapel or garden does not establish event permission: confirm attendance, suppliers, music rules and a wet-weather space separately.
Your group’s booking checklist
Send these details with your enquiry so we can compare the layout against your group, rather than guest capacity alone.
- Bedrooms and bathrooms
- List couples, single guests and children by age. Request available floor plans, bed arrangements and a room-by-room en-suite list; a bathroom total does not establish private access for every bedroom.
- Access between buildings
- Flag anyone who needs step-free access or a bedroom near the main living areas. Check stairs, paths and the location of any annex before assigning rooms.
- Eating and celebrating together
- State the number staying and any visiting guests. Request indoor and outdoor seating capacities, a wet-weather plan and written confirmation of event, catering and music arrangements.
- Dates and total cost
- Give your dates and flexibility. Ask which buildings, services and charges the quote includes, together with pool opening dates and any heating costs.
See villas accommodating 16 guestsSee villas accommodating 20 or more
The largest villas
Space to stay
and gather together.
The villas on this page are the ones built for a crowd — the wedding party, the leadership offsite, the reunion that finally gets three generations under one roof.
Each listing sleeps twelve or more. Compare the bedroom layout, en-suite bathrooms and shared dining spaces as well as capacity. If your group needs more than one villa, ask us to confirm availability, distances between properties and where everyone can eat together.
If you are gathering for a particular reason, start from the occasion and confirm the arrangements with the property for weddings, corporate retreats and family reunions and milestone birthday celebrations.
By exact party size: villas for 12, for 16 and for 20 or more.
Before you enquire, two honest reads: what a villa at this scale costs and how renting works. The top of the collection is at luxury villas.
Enquire
Tell us your numbers, and we’ll tell you the right villa.
Choose a large villa by layout, not just guest count
A large villa in Tuscany needs to work for sleeping, eating and spending time together. Begin with your overnight guest list, then compare bedrooms, bathrooms and shared spaces. A villa accommodating 24 may suit a party of 18 wanting more room, but the extra capacity alone does not tell you where those rooms are.
Villa Elle offers accommodation across three buildings; Villa della Cappella has its nine bedrooms on upper floors; Villa Controni combines twelve en-suite bedrooms with several reception rooms. These are different ways of staying together. Ask for available floor plans before assigning rooms, especially when parents want to be close to children or someone needs to avoid stairs.
If your numbers are settled, use the collections for 16 guests or 20 guests and more to narrow the inventory. Both include larger villas that can accommodate that party size; they are not lists restricted to exactly sixteen or twenty beds.
Bedrooms and en-suites: build the rooming plan first
Eight couples sharing one bedroom per couple need eight suitable bedrooms; ten couples need ten. Families, single travellers and children sharing may need a different arrangement. Check double versus twin beds, any additional beds, and whether bedrooms are in the main villa, an annex or a separate building.
A total of twelve bathrooms does not prove that twelve bedrooms are en-suite. Request a bedroom-by-bedroom list showing private and shared bathrooms, connecting rooms and access routes. Where step-free access matters, confirm the route from parking to the bedroom, bathroom and communal spaces, not just the presence of a ground-floor room.
For three generations, consider how the layout works after dinner as well as during the day. Rooms away from the main gathering space may suit early sleepers, while families with young children may prefer adjacent bedrooms. Our family gathering guide helps turn the guest list into a practical brief.
Dining together, indoors and outside
Confirm the number that can sit at one table in each dining space. A terrace large enough for everyone in July does not establish that the group can eat together indoors on a wet October evening. Ask about chairs, covered space and the room available for service around the table.
The same check applies to living rooms: can the whole party gather comfortably, and is there a second space for guests who want a quieter evening? Villa Controni’s several living rooms and Villa della Cappella’s salon and games room offer different starting points for this comparison.
For a shared dinner, ask about private chef arrangements, kitchen access, menus, food costs, service and clearing up. Confirm what is included in the villa rate and what is quoted separately. For autumn dates, use the October villa checklist to cover heating and seasonal pool arrangements too.
A birthday dinner is different from an event booking
For a 30th, 40th, 50th or 70th birthday, start with the kind of celebration you want: dinner for the resident guests, a catered lunch with visitors, or an event with music and suppliers. Give the owner the total attendance as well as the number sleeping at the villa.
Confirm the permitted event space, an indoor alternative, supplier access, music hours, additional fees and any restrictions before committing. A private chapel, banquet hall or extensive garden can be a useful feature, but does not by itself establish permission for a ceremony or party.
Our birthday celebration guide covers the occasion in detail. For a wedding, compare venue arrangements separately from the accommodation: resident capacity and permitted event attendance answer different questions.
Compare the whole weekly cost
Use the weekly villa rate as the starting point, then compare the same dates, room access and inclusions. As an illustration, a €30,000 rental divided among twenty paying guests is €1,500 each for the week before separately charged services. This is arithmetic, not a quoted rate for every villa on this page.
Request an itemised quote covering catering, staffing, heating, pool heating where available, transfers and any event charges that apply. Deposits and payment dates should be clear before the group commits. Our villa pricing guide explains the questions to ask.
Enquire once your likely dates and group size are known, particularly if a specific layout is essential. Do not assume a birthday weekend can be booked for two nights: minimum stays and arrival days depend on the villa and season.
Choose a base that works for the whole group
Start with the outings that matter most and compare them with the villa’s location. Villas near Lucca suit a different itinerary from villas near Siena. Our map and driving-distance guide helps compare the areas without treating Tuscany as one compact destination.
Before booking flights, use the Tuscany airport guide to compare arrival options, then confirm the route to the exact property. For several households, discuss arrival times, luggage, child seats and the size of vehicles that can reach the villa.
If your party exceeds one property’s capacity, ask about combining villas. Confirm availability, the real distance between them and which property permits everyone to gather for meals. Two villas on the same estate are not necessarily within easy walking distance.
Frequently asked
- How do we choose between villas for 16, 18 and 24 guests?
- Start with the number and type of bedrooms your guests need. Then compare en-suite arrangements, the location of annexes and indoor dining capacity. A larger villa can give a smaller party more flexibility, but confirm which rooms and buildings are included in the quote.
- Do all large villas have en-suite bathrooms?
- No collection-wide assumption should be made. Request the bathroom arrangement for each bedroom. A total bathroom count can include shared bathrooms and guest WCs, so it is not the same as an en-suite count.
- Can we see floor plans before booking?
- Ask for available floor plans and a room-by-room breakdown for the villas on your shortlist. Confirm bed types, bathrooms, stairs and distances between buildings. If a plan is unavailable, request those details directly before allocating rooms.
- Can we hold a birthday celebration at a large villa?
- Confirm the proposed celebration with the owner before booking. Explain the number of resident and visiting guests, catering, music and suppliers. Sleeping capacity does not establish event permission; check the event space, indoor alternative and any additional charges.
- Can a group of 30 or more stay together?
- Ask about options for your exact group size, including multiple properties where appropriate. Availability, distance between villas and permission for shared meals must be confirmed. Do not assume adjoining accommodation can be added to an existing booking.
- How much does a large villa cost per person?
- Divide the confirmed weekly rental by the number of paying guests, then add separately charged services. For example, a €30,000 rental shared by twenty paying guests is €1,500 each before extras. Rates and inclusions vary by villa and dates.
- What should we check for an October group stay?
- Confirm indoor dining and seating for the whole group, villa heating, pool opening and any pool-heating arrangements. For a celebration, request a suitable indoor alternative and written confirmation of the event arrangements.