Top 10 Large Holiday Homes & Group Villas near Siena
Ranking updated on 2026-10-18
Siena and its surrounding Tuscan countryside — the Chianti hills, the Val d'Orcia, the Crete Senesi — draw groups of 10 to 40 people for some of the most meaningful occasions in their lives: milestone birthdays, wedding celebrations, corporate seminars, and multi-generational family reunions. The region offers something rare in group travel: genuine privacy on large rural estates, medieval architecture within easy driving distance, and a landscape that looks exactly as good in person as it does in photographs. Villas and farmhouses here come with the scale a group actually needs — long terraces for shared dinners, private pools, olive groves, and vineyards — without sacrificing proximity to some of Italy's most iconic cities and villages.
CasaGiga currently lists 48 properties within roughly 80 km of Siena — a zone we define as within about 1 hour 30 minutes of the city. The largest property sleeps up to 40 guests, and the average nightly price stands at €77 per person, with rates starting from €47 per person per night. The properties in this zone sit an average of 28 km from Siena's centre. Across all listings, guests have submitted 11,063 verified reviews, producing a collective average rating of 4.7 out of 5 — figures computed on 4 September 2026 and refreshed every night.
The ranking below places online-bookable properties first — because instant confirmation genuinely reduces planning stress for group trips — then orders the remaining houses by average guest rating and volume of verified reviews; hosts who display this ranking on their own website also earn a stable position in the list.
The area in numbers
The ranking
1CasaGiga 2695 (Siena)
📍 Siena, Toscana · 47 km
👥 14 guests4.7★ (36 reviews)🏡 VillaA six-bedroom villa in Siena sleeping up to 14 guests, rated 4.7 across 36 reviews. Located about 47 km from the city centre, it is available to book online instantly at €123 per person — making it the only fully bookable CasaGiga in this selection.
⚡ Bookable onlinefrom 123 € / person / nightSee this CasaGiga →
2CasaGiga 74 (Siena)
📍 Siena, Toscana · 27 km
👥 10 guests4.8★ (160 reviews)🌳 EstateA five-bedroom estate 27 km from Siena with room for up to 10 guests, earning a 4.8 rating from 160 reviews. Priced from €61 per person, it is available on request rather than instant online booking.
On requestfrom 61 € / person / nightSee this CasaGiga →
3Agriturismo - La Corte del Sole
📍 Provincia di Siena, Toscana · 3 km
👥 0 guests5.0★ (67 reviews)🌻 Provencal farmhouseA Provençal-style farmhouse in the Provincia di Siena, just 3 km from the city, holding a perfect 5-star rating from 67 guests — an exceptional benchmark in this zone. Group capacity and availability are confirmed directly with the host; online booking is not offered.
On requestSee this CasaGiga →
4Agriturismo I Roseti
📍 Provincia di Siena, Toscana · 45 km
👥 0 guests5.0★ (45 reviews)🌻 Provencal farmhouseAgriturismo I Roseti is a Provencal farmhouse located in the Provincia di Siena, roughly 45 km from the city. It holds a flawless 5-star rating earned across 45 reviews, placing it among the most consistently praised properties in the zone. Booking is arranged through direct contact rather than online reservation.
On requestSee this CasaGiga →
5IL LAVANDETO - farmhouse in the city
📍 Siena, Toscana · 3 km
👥 0 guests4.9★ (172 reviews)🌻 Provencal farmhouseIL LAVANDETO brings farmhouse character into Siena itself, only 3 km from the historic centre, with a 4.9-star rating drawn from 172 reviews. Its unusual urban-rural positioning sets it apart; group details and reservations are handled directly with the property.
On requestSee this CasaGiga →
6Agriturismo Allevamento Renaccino
📍 Siena, Toscana · 5 km
👥 0 guests4.9★ (127 reviews)🌻 Provencal farmhouseSet 5 km from Siena, Agriturismo Allevamento Renaccino is a Provençal farmhouse with a consistent 4.9-star rating earned across 127 guest reviews. Group capacity and room configuration are confirmed on request; reservations are made directly with the host rather than online.
On requestSee this CasaGiga →
7Agriturismo Casalino18
📍 Provincia di Siena, Toscana · 6 km
👥 0 guests4.9★ (89 reviews)🌻 Provencal farmhouseAgriturismo Casalino18 is a well-regarded Provençal farmhouse in the Provincia di Siena, just 6 km from the city, rated 4.9 stars by 89 guests. It sits close enough to Siena to serve as a practical regional base. Group sizing and booking are handled directly with the host.
On requestSee this CasaGiga →
8Agriturismo San Sano
📍 San Sano, Toscana · 12 km
👥 0 guests4.9★ (323 reviews)🌻 Provencal farmhouseAgriturismo San Sano in San Sano, 12 km from Siena, is among the most-reviewed properties in this zone — 323 guests have given it a 4.9-star rating. Group capacity and booking details are confirmed by contacting the host directly; no online reservation is available.
On requestSee this CasaGiga →
9Podere Felceto
📍 Panzano In Chianti, Toscana · 25 km
👥 0 guests4.9★ (80 reviews)🌻 Provencal farmhousePodere Felceto is a Provençal farmhouse in Panzano in Chianti, 25 km from Siena in the heart of Chianti Classico country. Its 4.9-star rating from 80 guests reflects a strong track record; group details and booking are arranged directly with the property.
On requestSee this CasaGiga →
10The Secret of Pietrafitta
📍 Provincia di Siena, Toscana · 26 km
👥 0 guests4.9★ (327 reviews)🌻 Provencal farmhouseThe Secret of Pietrafitta, within the Provincia di Siena and 26 km from the city, is the most-reviewed farmhouse in this selection — 327 guests have awarded it 4.9 stars. Group capacity and availability are confirmed directly with the host; online booking is not currently offered.
On requestSee this CasaGiga →
How to Choose the Right Group House near Siena
A property listed as sleeping 14 guests across 6 bedrooms looks clear on paper, but the arrangement of those beds matters enormously for groups. Always request a room-by-room layout before confirming: couples typically need a double, friends sharing may be fine with twins, and children may require a cot or rollaway. Check whether bathrooms are en-suite or shared across multiple rooms, and confirm whether extra beds are available at additional cost. The gap between advertised capacity and genuinely comfortable capacity is often one or two guests.
Rural Tuscany is quiet by nature, and most properties in the Siena zone impose noise curfews — typically 11 pm to midnight — out of respect for neighbouring farms and villages. Ask the host explicitly whether music is permitted for a birthday dinner or celebration, and whether it must remain indoors. Properties operating under Italy's agriturismo licence are generally prohibited from hosting amplified events or commercial gatherings. Make sure the rental contract explicitly permits your intended use before paying any deposit.
If your group includes young children, pool safety deserves careful attention. Most private pools in the Siena countryside are unfenced and uniform in depth — beautiful but requiring active supervision at all times. Ask whether an alarm system or perimeter gate is available. Also confirm whether pool heating is included in the rental price; in spring and autumn it adds real comfort but typically costs an additional €150 to €300 per week. Outdoor kitchens, pizza ovens, and barbecue areas are common and worth verifying ahead of arrival.
Properties in this zone range from 3 to 47 km from central Siena, and rural locations mean a rental car — ideally one per couple or sub-family — is essential. Check that the property has adequate off-road parking for your vehicles. On the financial side, most hosts require a security deposit of €500 to €1,500 payable at check-in, and cancellation windows for large groups often begin 60 to 90 days before arrival. Get the full refund deadline confirmed in writing before transferring any balance beyond the initial deposit.
By occasion
Milestone Birthday Parties in the Tuscan Countryside
A milestone birthday for a group of 12 to 14 finds its match at CasaGiga 2695 in Sant'Albino, a 14-person villa with 6 bedrooms situated 47 km from Siena — private enough for a proper celebration, yet close enough for a day trip into the city. Groups of exactly 10 might prefer CasaGiga 74 in San Gimignano, where the estate sits within sight of the medieval towers. Both offer the outdoor dining space and privacy that a birthday dinner under the Tuscan sky genuinely requires.
Wedding Celebrations and Pre-Wedding Gatherings
For a wedding party or a week-long pre-wedding gathering, the Siena countryside provides an unrivalled backdrop: photogenic landscapes at every turn and a medieval city a short drive away for the civil ceremony itself. Agriturismo La Corte del Sole, rated a perfect 5.0 by 67 guests and just 3 km from Siena's centre, offers the intimate farmhouse atmosphere that photographs brilliantly. Confirm with the host that private celebrations are permitted under the property's agriturismo operating licence before finalising any details.
Corporate Seminars and Team Off-Sites
For corporate retreats and working seminars, what matters most is reliable Wi-Fi, a large table where the whole team sits together, and enough private rooms to separate focus time from leisure. CasaGiga 74 in San Gimignano, an estate rated 4.8 across 160 verified reviews, offers the consistency and scale a professional group of 10 needs for a productive off-site. The San Gimignano area also provides excellent restaurant options for team dinners. Ask the host about dedicated workspace and connection speed before confirming.
Multi-Generational Family Reunions
Reuniting three generations under one Tuscan roof means finding a property that genuinely works for grandparents, parents, and children simultaneously: ground-floor bedrooms, pool access without steep steps, generous shade, and enough bathrooms to avoid queues. CasaGiga 2695 in Sant'Albino, sleeping 14 across 6 bedrooms, has the room count to give every couple and sibling group their own space without compromise. Families drawn to Chianti country will find Podere Felceto in Panzano in Chianti, rated 4.9 by 80 guests, a compelling alternative with vineyard views.
Frequently asked questions
What does it cost to rent a group house near Siena for 20 people?+
Prices across CasaGiga listings in this zone start at €47 per person per night, with an average of €77. For 20 guests over 5 nights, that works out to roughly €7,700 at the average rate — before cleaning fees, tourist tax, and security deposit. Larger properties with private pools and more bedrooms sit toward the higher end; booking several months in advance typically secures the best available rate.
Are we allowed to have a party or play music at these houses?+
It depends on the property and local regulations. Most rural houses in the Siena area impose a noise curfew between 11 pm and midnight. Agriturismi operating under Italy's agriturismo licence are generally not permitted to host amplified events or music for external guests. Always ask the host directly and get written confirmation before booking — especially if live music, a DJ, or a large outdoor dinner is part of your plans.
How does CasaGiga decide which houses appear at the top of this ranking?+
Online-bookable properties appear first, because instant booking confirmation removes the uncertainty that affects group planning most. Remaining houses are ordered by average guest rating combined with the volume of verified reviews — a 4.9 from 300 guests outranks a 4.9 from 30. Hosts who display this ranking on their own website also earn a stable position. The list is recomputed every night using live data.
How do I book one of these group houses near Siena?+
CasaGiga 2695 in Sant'Albino can be reserved instantly online through the CasaGiga platform. For the other listings, click through to the property page and use the enquiry form to contact the host directly. Include your exact dates, the total number of guests, and a brief description of the occasion — this lets hosts respond with a tailored quote rather than a generic reply, which speeds up the process considerably for large group bookings.
Is tourist tax included in the prices shown?+
In most cases, no. Italy's tourist tax (tassa di soggiorno) is set by each municipality and collected separately, usually in cash on arrival. Rates in the Siena province typically range from €1 to €4 per person per night depending on location and property category. For a group of 20 staying 5 nights, that can add €200 or more to the total bill. Always confirm the exact amount with the host when you make your enquiry.
Is there a minimum number of nights required for a group booking?+
Most properties in the Siena countryside require a minimum stay of 5 to 7 nights during peak summer season (July–August) and around major holidays. Some hosts insist on a full Saturday-to-Saturday week in high season. Shorter stays of 3 to 4 nights are more commonly available in spring and autumn. Check the property's specific conditions when you enquire, as flexibility varies considerably from host to host.
What time is check-in, and can members of our group arrive at different times?+
Standard check-in for rural Tuscan properties falls between 3 pm and 6 pm, with check-out typically by 10 am or 11 am. Flexible arrival windows can often be arranged if you communicate early — especially useful when a large group is travelling from different cities. Some properties charge an additional fee for arrivals after 8 pm. Designate one person in the group to coordinate logistics and liaise directly with the host.
What happens if the house we want is already booked for our dates?+
Use the enquiry form to ask about a waitlist or alternative dates — cancellations on peak-season bookings do occur. CasaGiga lists 48 properties in the broader Siena zone, so adjusting your group-size filter or shifting dates by a week often surfaces a comparable alternative. If nothing fits immediately, the enquiry form connects you with our team, who can suggest properties not yet fully visible through standard search filters.
How this ranking is made
Properties are ranked by booking availability first — online-bookable listings take the leading positions — then by average guest rating weighted by the total number of verified reviews, so a 4.9 from 300 guests ranks above a 4.9 from 30. Hosts who display this ranking on their own website retain their position as recognition of the mutual visibility they provide to travellers researching the area.
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