
Siena · Sleeps 24 · 12 bedrooms
From €1,929 / night
Situated in sought-after Chianti wine country, within easy reach of Siena and Florence
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 house? Browse all large villas in Tuscany and compare guest capacity before planning the occasion.
The houses
A starting shortlist. Confirm availability, room arrangements and permission for your celebration before booking.
19 houses

Siena · Sleeps 24 · 12 bedrooms
From €1,929 / night
Situated in sought-after Chianti wine country, within easy reach of Siena and Florence

Cortona · Sleeps 18 · 9 bedrooms
From €1,450 / night
A genuine 17th-century restoration: frescoed vaulted ceilings, painted walls and terracotta floors across more than 1,000 square…

Lucca & Garfagnana · Sleeps 24 · 12 bedrooms
From €3,300 / night
A whole private hamlet, twelve en-suite bedrooms for up to twenty-four, made for a large gathering…

Lucca & Garfagnana · Sleeps 24 · 12 bedrooms
From €3,150 / night
A 19th-century Lucchese villa of real history, the Controni family's summer residence…

Chianti · Sleeps 18 · 9 bedrooms
From €2,500 / night
Four private flats across two stone farmhouses on the Greve riverbank, each with its own kitchenette and living room…

Chianti · Sleeps 18 · 9 bedrooms
From €2,900 / night
History on paper: a 1427 document from Bernardo di Bartolomeo Gherardi already describes this farm's forests, soil…

Maremma · Sleeps 18 · 9 bedrooms
Price on enquiry
Restored over a decade by artisans who handcrafted almost every element, locally quarried stone, hand-forged iron…

Lucca & Garfagnana · Sleeps 14 · 7 bedrooms
From €2,150 / night
A genuine 17th-century aristocratic villa, built in 1624 for Count Cosimo Bernardini…

Dimora Ghirlandaio · Sleeps 10 · 5 bedrooms
Price on enquiry
Renaissance heritage, a 600-year-old artistic hamlet once home to the Ghirlandaio family…

Montepulciano · Sleeps 12 · 6 bedrooms
From €1,900 / night
The only villa in the Val d'Orcia with a private wellness centre of its own: an indoor pool heated to 38°C with hydromassage…

Castelfalfi · Sleeps 6 · 3 bedrooms
From €10,000 / night
A restored barn with the volume and light only an old fienile gives: high ceilings, broad openings, a real sense of space.

Castiglion del Bosco · Sleeps 11 · 6 bedrooms
From €15,500 / night
Six en-suite bedrooms for eleven, across the main house, a guest annex and a pool house.

Lucca & Garfagnana · Sleeps 8 · 4 bedrooms
From €1,050 / night
An atmospheric conversion of a 16th-century olive mill, working until 1997, with original features and ancient oil jars in the…

Lucca & Garfagnana · Sleeps 14 · 6 bedrooms
From €2,700 / night
An award-winning contemporary masterwork, designed by its owner-architects and named by National Geographic among Italy's most…

Lucca & Garfagnana · Sleeps 15 · 8 bedrooms
From €2,150 / night
A classic restored Tuscan country home, terracotta, beams and frescoes, with rose-covered patios and a winter-garden conservatory.

Lucca & Garfagnana · Sleeps 14 · 7 bedrooms
From €1,700 / night
A characterful Tuscan farmhouse with genuine history, the home of Felice Matteucci, father of the combustion engine.

Castiglion del Bosco · Sleeps 12 · 6 bedrooms
Price on enquiry
Six en-suite bedrooms for twelve, with a self-contained guest annex and kitchenette, room for a large family or group.

Castiglion del Bosco · Sleeps 8 · 4 bedrooms
From €13,500 / night
Four en-suite bedrooms for eight, including a private guest annex, and a separate pool house with a kitchenette.

Castiglion del Bosco · Sleeps 12 · 6 bedrooms
Price on enquiry
Six en-suite bedrooms for twelve, across the main house and a pool house, generous space for a large group.
The occasion
A big family gathering works when the house 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 houses, 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 houses 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 houses, 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 house: 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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