Villa Cecconi | 12-Bedroom Villa in Poggibonsi (Siena) Province of Sie

Twenty-four guests. Twelve separate bedrooms. Twelve pristine bathrooms. A 16-metre pool overlooking San Gimignano’s medieval towers. This luxury villa rental in Poggibonsi, Siena sits at the heart of Chianti wine country, where Tuscan hillsides roll toward Florence and centuries-old stone villages punctuate the landscape. Villa Cecconi transforms the challenge of housing a large group into an elegant, manageable reality—part 14th-century watchtower, part thoughtfully restored annexes, entirely capable of hosting extended families, wedding parties, or multi-generational celebrations across three interconnected stone buildings.

Inside Villa Cecconi

Villa Cecconi sleeps 24 guests across 12 bedrooms and 12 bathrooms distributed throughout its three structures. The property’s layout prioritizes both communal gathering and private retreat.

The Main Villa anchors the complex—the original medieval watchtower restored with exposed stone walls, wooden beam ceilings, and terracotta tile floors throughout. Ground floor accommodations include a fully equipped commercial-scale kitchen positioned for serious meal preparation, a formal dining room seating up to 26 guests around an extended table, a modest living room, a television room equipped with satellite channels in English and Italian, and a guest bathroom with integrated laundry facilities. Ascending the stone staircase, seven double bedrooms occupy the first floor, each with its own ensuite bathroom and individual climate control—these rooms retain period character while offering contemporary comfort.

The Secondary Villa functions as a self-contained residence ideal for families seeking semi-independence. Ground floor contains a full kitchen, guest bathroom, living room, and one double bedroom with ensuite. The first floor holds three additional double bedrooms with ensuite bathrooms. This building operates efficiently as a separate unit while remaining footsteps from the main villa’s communal spaces.

The Cottage deserves particular note for its accessibility design—fully wheelchair-accessible with level entry, accessible bathroom, and a double bedroom specifically configured for guests with mobility requirements. The space includes its own kitchen-dining area, offering independence and dignity for guests who need it. All bedrooms throughout the property feature air-conditioning with individual thermostat control.

Outdoor Spaces and Living

The grounds extend across several acres of landscaped gardens. A 500-metre driveway lined with tall cypress trees and blooming rose gardens creates the initial approach—immediately establishing the property’s scale and sophistication. Two distinct parking areas accommodate up to 8 vehicles.

The swimming pool spans 16 metres by 9 metres with an infinity edge, open seasonally from the second Saturday in May through the final Saturday of September. The water temperature reflects the Mediterranean climate; early summer and late September offer the most comfortable conditions. Beyond the pool, a large gazebo with outdoor furniture creates an all-weather gathering space—this is where long Tuscan lunches happen, where conversations drift from mid-morning into afternoon shadows.

A wood-fired pizza oven and full barbecue station occupy the garden’s lower levels, equipped for guests who want to cook. The setting—surrounded by vineyards with San Gimignano’s towers visible across the valley—transforms ordinary meals into memorable events. This is the kind of outdoor kitchen where reluctant cooks volunteer to prepare dinner.

Location: Poggibonsi (Siena) and the Surrounding Area

Villa Cecconi occupies the Chianti region’s northern edge, approximately 48km south of Florence and just 20km east of Siena. Poggibonsi itself is a modern, functional market town 5 kilometres away, home to essential services including supermarkets where you can source fresh produce daily. The town’s Tuesday farmer’s market supplies vegetables, cheeses, and cured meats that define Tuscan cooking.

San Gimignano lies 15 kilometres north—one of Tuscany’s most iconic medieval hill towns, famous for its 13 stone towers silhouetting the skyline. The town’s restaurants, pizzerias, and cafés line narrow cobbled streets. Siena, 20 kilometres south, represents Renaissance grandeur: the Piazza del Campo’s shell-shaped piazza, the striped marble Duomo, the Palazzo Pubblico with its Torre del Mangia climbing 102 metres. Thursday’s farmer’s market in San Gimignano operates alongside artisan food shops selling wines, olive oils, and traditional sweets like panforte and ricciarelli.

The wider region offers cultural depth: the Monteriggioni fortress village (12km), Volterra’s alabaster workshops and Etruscan Museum (30km), and countless working wineries throughout Chianti Classico territory producing the region’s signature Nebbiolo and Sangiovese varieties. Chianti’s cycling routes connect villages through vineyard roads; rental agencies in Poggibonsi supply bicycles for day-long exploration.

Florence—approximately 48km north via the SR222 Chiantigiana road or 50 minutes by train from Poggibonsi station—houses the Uffizi Gallery, Accademia (home to Michelangelo’s David), and Brunelleschi’s Duomo with its distinctive terracotta dome. Seasonal considerations matter: May through September brings peak tourism and warm, reliable weather; April and October offer cooler temperatures and smaller crowds. July-August heat can be intense; many locals retreat to the coast. The Palio, Siena’s historic horse race, occurs August 16th and July 2nd, drawing international crowds and requiring accommodation bookings months in advance.

For inspiration on regional highlights, explore our Tuscany travel guide, or browse luxury villas across Europe and our dedicated collection in the Province of Siena.

Who This Villa Suits Best

Multi-generational family reunions: The cottage’s wheelchair accessibility, combined with three separate buildings, allows different age groups privacy while maintaining proximity. Grandparents can rest while children use the pool; teenagers occupy one villa while parents host in the main house.

Wedding parties and celebrations: The 26-person dining table, outdoor gazebo, pizza oven, and accommodations for 24 guests create a self-contained celebration venue. Couples planning Tuscan ceremonies often rent the entire property for rehearsal dinners and multi-day festivities.

Corporate retreats and leadership groups: The commercial kitchen supports catering; satellite television and reliable Wi-Fi accommodate both work and leisure. Groups can conduct day meetings, then gather for team dinners around the main table.

Friend groups seeking shared adventure: The property’s layout means eight friends can occupy the secondary villa while another eight take the main villa’s bedrooms, maintaining group cohesion without forced togetherness. The pool and outdoor spaces become natural gathering points.

Families with accessibility needs: The cottage’s wheelchair access, ground-floor bedroom, and accessible bathroom make Villa Cecconi genuinely functional—not an afterthought—for guests with mobility considerations.

Practical Information

Capacity & Layout: Villa Cecconi accommodates 24 guests across 12 bedrooms (all doubles) and 12 bathrooms distributed across three buildings. All bedrooms feature air-conditioning with individual climate control.

Nearest Airport: Florence Airport (Peretola), approximately 55 kilometres north, handles most international arrivals. Transfer time to Villa Cecconi is roughly 70 minutes by car. Siena, 20 kilometres south, lacks a commercial airport; Pisa International Airport (100km, 90-minute drive) serves as an alternative for some travellers.

Local Services: Poggibonsi, 5 kilometres away, contains supermarkets, pharmacies, and other essentials. Siena’s larger commercial centre lies 20km distant.

What’s Included: Maid service, chef/cook availability, breakfast arrangements, full catering options, airport transfers, yoga classes, cooking classes, pre-stocked refrigerator, Wi-Fi throughout all buildings, and utilities covering air-conditioning and pool maintenance (seasonal). Satellite television with English and Italian channels operates in all common areas.

Check-in Flexibility: Contact Excellence Luxury Villas directly to discuss specific arrival times and any early check-in arrangements required for large group coordination.

Frequently Asked Questions about Villa Cecconi

How many guests does Villa Cecconi sleep?

Villa Cecconi accommodates 24 guests maximum across 12 double bedrooms and 12 bathrooms. The breakdown includes seven bedrooms in the main villa, four bedrooms in the secondary villa, and one accessible bedroom in the cottage. This capacity makes it suitable for extended families, multiple families travelling together, or celebration groups like weddings or milestone birthday parties.

What is the nearest airport to Villa Cecconi in Poggibonsi (Siena)?

Florence Airport (Aeroporto Amerigo Vespucci), 55 kilometres north, serves as the primary gateway. Transfers take approximately 70 minutes by private car, typically arranged through Excellence Luxury Villas. Pisa International Airport (100 kilometres, 90-minute drive) offers an alternative, particularly for international flights with more frequent international carrier service. Siena lacks a commercial airport but sits only 20 kilometres from Villa Cecconi.

What is the best time of year to rent Villa Cecconi?

May through September offers warm, reliable weather and open pool season (May’s second Saturday through September’s final Saturday). April and October provide cooler, pleasantly mild conditions with fewer tourists and lower accommodation pressure. December through February brings occasional rain and cooler temperatures, suitable for guests seeking solitude and contemplative countryside walks. Avoid August 15th-16th if the Siena Palio horse race creates unwanted crowds in the region. November and early December offer harvest season charm—olive pressing occurs, autumn colours persist, and the region feels less commercial.

Is Villa Cecconi suitable for families with children?

Yes, with reservations. The 16-metre swimming pool provides water recreation; however, formal lifeguard supervision is not provided—families must arrange their own child supervision. The property contains open garden areas and stone staircases requiring parental attention. Ground floor bedrooms in the cottage and secondary villa ease family logistics. San Gimignano (15km) and Siena (20km) contain family-friendly restaurants; neither location specializes in children’s entertainment infrastructure. The property’s layout suits multigenerational families where grandparents provide supervision while parents relax.

What is included in the rental price at Villa Cecconi?

Standard inclusions encompass utilities (electricity, water, heating/air-conditioning), Wi-Fi internet access throughout all buildings, satellite television service, weekly housekeeping and linen changes, fully equipped kitchens with cookware and serving equipment, and access to outdoor amenities (gardens, gazebo, pool during seasonal operation). Premium services available at additional cost include professional chef services, private cooking classes, yoga instruction, massage and beauty treatments, catering for special events, airport transfers, and pre-stocking of the refrigerator with groceries of your choice. Contact Excellence Luxury Villas to clarify which specific services are included in your booking terms.

What restaurants and shops are near Villa Cecconi?

Poggibonsi (5km) contains practical supermarkets and everyday shopping. San Gimignano (15km) offers dining ranging from casual pizzerias to fine restaurants; Ristorante Bel Soggiorno and Il Pino command local reputations. Siena’s Piazza del Campo district (20km) surrounds multiple traditional trattorie serving handmade pasta and wild boar ragù. The Tuesday farmer’s market in Poggibonsi and Thursday market in San Gimignano supply fresh vegetables, artisanal cheeses, cured meats (particularly wild boar products), and Chianti wines. For serious wine tasting, dozens of working wineries operate throughout the surrounding countryside; Château Brolio and Castello di Ama represent prominent examples offering formal tastings and restaurant facilities.