
Siena · 24 guests · 12 bedrooms
From €13,503 / week
Panoramic view · Step-free access
For the gathering: Pizza oven
OccasionsFamily Reunions & Celebrations
Exclusive Tuscany helps families choose private villas for reunions and multigenerational gatherings in Tuscany. Start with the number of overnight guests, bedroom layout and dates; then confirm dining capacity, pool safety and access for everyone in the group. Ask for floor plans, the en-suite bedroom breakdown and details of indoor and outdoor event spaces before choosing.
Still choosing the size of villa? Browse all large villas in Tuscany and compare guest capacity before planning the occasion.
The villas
A starting shortlist. Confirm availability, room arrangements and permission for your celebration before booking.
36 villas

Siena · 24 guests · 12 bedrooms
From €13,503 / week
Panoramic view · Step-free access
For the gathering: Pizza oven

Cortona · 18 guests · 9 bedrooms
From €10,150 / week
Private chapel · Frescoed interiors
Occasions: Hosts family celebrations, weddings · Pizza oven

Chianti · 18 guests · 9 bedrooms
From €20,300 / week
Infinity pool · Working vineyard
History on paper: a 1427 document from Bernardo di Bartolomeo Gherardi already describes this farm's forests, soil…

Lucca & Garfagnana · 24 guests · 12 bedrooms
From €23,200 / week
Fully staffed · Wine cellar
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef

Lucca & Garfagnana · 24 guests · 12 bedrooms
From €22,000 / week
Fully staffed · Private chapel
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef

Dimora Ghirlandaio · 37 guests · 20 bedrooms
From €91,000 / week
Fully staffed · Spa
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef · Pizza oven

Chianti · 22 guests · 9 bedrooms
From €11,160 / week
Heated pool · Cinema room
Occasions: Hosts family celebrations · Pizza oven

Val d'Orcia · 26 guests · 13 bedrooms
From €22,344 / week
Spa · Infinity pool
Occasions: Hosts family celebrations, weddings, corporate retreats

Montalcino · 24 guests · 12 bedrooms
From €30,730 / week
Panoramic view
Occasions: Hosts family celebrations, weddings, corporate retreats

Chianti · 26 guests · 13 bedrooms
From €67,900 / week
Spa · Working vineyard
Occasions: Hosts family celebrations, corporate retreats · Private chef

Chianti · 19 guests · 10 bedrooms
From €59,500 / week
Spa · Heated pool
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef · Pizza oven

Chianti · 18 guests · 9 bedrooms
From €17,400 / week
Working vineyard · Olive grove
Four private flats across two stone farmhouses on the Greve riverbank, each with its own kitchenette and living room…

Chianti · 20 guests · 10 bedrooms
From €13,500 / week
Spa · Gym
Occasions: Hosts family celebrations, weddings

Maremma · 18 guests · 9 bedrooms
Price on enquiry
Fully staffed · Spa
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef

Lucca & Garfagnana · 14 guests · 7 bedrooms
From €15,000 / week
Fully staffed · Frescoed interiors
Occasions: Hosts family celebrations, weddings, corporate retreats · Private chef

Chianti · 8 guests · 4 bedrooms
From €4,500 / week
Panoramic view · Olive grove
Occasions: Hosts family celebrations

Montepulciano · 12 guests · 6 bedrooms
From €13,125 / week
Spa · Infinity pool
Occasions: Hosts family celebrations, weddings, corporate retreats

Castelfalfi · 6 guests · 3 bedrooms
From €70,000 / week
Working vineyard · Panoramic view
Occasions: Hosts family celebrations, weddings

Castiglion del Bosco · 11 guests · 6 bedrooms
From €108,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Heated pool · Panoramic view
Occasions: Hosts family celebrations · Pizza oven

Lucca & Garfagnana · 8 guests · 4 bedrooms
From €7,500 / week
Olive grove
Occasions: Hosts family celebrations · Private chef

Lucca & Garfagnana · 14 guests · 6 bedrooms
From €19,000 / week
Panoramic view · Olive grove
Occasions: Hosts family celebrations · Private chef

Lucca & Garfagnana · 15 guests · 8 bedrooms
From €15,000 / week
Frescoed interiors · Olive grove
Occasions: Hosts family celebrations, corporate retreats · Private chef

Lucca & Garfagnana · 14 guests · 7 bedrooms
From €12,000 / week
Fully staffed · Olive grove
Occasions: Hosts family celebrations · Private chef

Castiglion 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
Occasions: Hosts family celebrations · Pizza oven

Castiglion del Bosco · 8 guests · 4 bedrooms
From €94,500 / week
On the Rosewood resort estate: spa, restaurants and private golf on site
Infinity pool · Heated pool
Occasions: Hosts family celebrations

Castiglion 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
Occasions: Hosts family celebrations · Pizza oven

Montalcino · 8 guests · 4 bedrooms
From €24,500 / week
Working vineyard · Pet friendly
Occasions: Hosts family celebrations · Pizza oven

Chianti · 13 guests · 7 bedrooms
From €8,500 / week
Heated pool · Wine cellar
Occasions: Hosts family celebrations, weddings · Private chef · Pizza oven

Chianti · 14 guests · 7 bedrooms
From €7,810 / week
Spa · Infinity pool
Occasions: Hosts family celebrations · Pizza oven

Cortona · 12 guests · 7 bedrooms
From €20,700 / week
Infinity pool · Heated pool
Occasions: Hosts family celebrations · Private chef · Pizza oven

Chianti · 10 guests · 5 bedrooms
From €6,699 / week
Panoramic view · Olive grove
Occasions: Hosts family celebrations

Chianti · 12 guests · 6 bedrooms
From €9,500 / week
Spa · Heated pool
Occasions: Hosts family celebrations

Chianti · 12 guests · 6 bedrooms
From €8,000 / week
Gym · Panoramic view
Occasions: Hosts family celebrations

Arezzo · 12 guests · 6 bedrooms
From €4,570 / week
Heated pool · Panoramic view
Occasions: Hosts family celebrations

Val d'Orcia · 12 guests · 6 bedrooms
From €7,875 / week
Infinity pool · Pet friendly
Occasions: Hosts family celebrations, weddings · Pizza oven

Val d'Orcia · 12 guests · 6 bedrooms
From €14,150 / week
Heated pool · Gym
Occasions: Hosts family celebrations
The occasion
A big family gathering works when the villa fits the people. Count households as well as guests: couples may want their own bathrooms, children may need rooms close to their parents, and someone who struggles with stairs needs more than a ground-floor bedroom on a listing.
Tell us who is coming and how you want to spend the week. We can help you compare the villas, discuss a private chef and identify the practical details to confirm before you book.
Villa Elle and Villa della Cappella are among our best sellers. Start with these villas when putting together your shortlist, then compare the larger villas shown here if more than 16 people are staying overnight.
For a large gathering, match the bedrooms to the households before comparing the celebration spaces. Ask for floor plans and an en-suite bathroom breakdown, then confirm which indoor and outdoor areas can accommodate your planned dinner or event. Our large-group villa collection offers another way to compare villas, including villas for 20 guests or more.
For a multigenerational family reunion, check the route between bedrooms, bathrooms, the dining terrace and the pool. A ground-floor room does not by itself mean step-free access. Ask about internal steps, slopes, bathroom arrangements and the distance between separate buildings.
A family of 12 may need six double bedrooms, or a different mix of twins and doubles. For 16 or 20 guests, check how many people sleep in permanent bedrooms and whether everyone can eat together indoors if it rains. Compare large Tuscany villas by capacity, then ask us to confirm the room allocation.
Request the available floor plans before allocating rooms. Check bedroom locations by floor and building, double or twin beds, connecting rooms, stairs and routes to shared spaces. If a current plan is unavailable, ask for a written room-by-room layout.
Confirm how many bedrooms have their own en-suite bathroom, which bathrooms are shared and whether any are reached across a corridor. The total bathroom count alone does not tell you whether each couple or household has a private bathroom.
Ask for details of the actual event spaces: seated dining capacity indoors and outdoors, room for your intended setup, guest toilets, catering access and a covered or indoor alternative in bad weather. Confirm the permitted event guest count separately from overnight capacity, along with supplier access, music rules and any event fees.
Plan a dinner around the people staying at the villa: dietary requirements, children’s meals, seating and a wet-weather alternative. Private-chef availability, menus, service and costs need to be confirmed for your dates. If the reunion includes a milestone, our Tuscany birthday villa guide covers celebration planning.
Sleeping capacity is not event capacity. Visitors who are not staying overnight, amplified music, suppliers and any larger gathering require the owner’s agreement before booking.
A symbolic vow renewal or anniversary dinner still needs the property owner’s permission for the proposed gathering. Tell us whether you want a private meal for resident guests or a ceremony with additional visitors, a photographer and other suppliers. That distinction affects which villas can be considered.
Confirm cots, high chairs, pool barriers and supervision arrangements for the particular villa. Do not assume a pool is fenced or heated. Ask which bedrooms have air conditioning and whether shops and restaurants require a drive.
Keep part of the stay unscheduled, with optional outings for different interests. Our family villa holiday guide and family activities can help you plan days together without expecting everyone to follow the same timetable.
Agree the accommodation budget and how households will share it before choosing a villa. Compare the price for your actual dates, then request a breakdown of chef service, groceries, transfers, pool heating, local taxes and any other extras. A security deposit is separate from the holiday spending budget.
For example, an accommodation quote of €18,000 shared by 18 people is €1,000 per person for the stay, before extras. This is illustrative arithmetic, not a villa price or package offer. If you need more space than one property provides, ask about options and confirm the travel distance between them.
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