Offering panoramic vistas over Chianti’s rolling hills and woodlands, Villa Gaiole is a serene Tuscan retreat that sleeps up to 14 guests across seven luxurious bedrooms. This 400-year-old property, once a rustic farmhouse surrounded by vineyards and olive groves, has been beautifully restored to balance historic charm with modern comfort.
The villa is divided between the main building and a smaller annexe, both full of character with exposed beams, stonework, and open fireplaces. Inside, you’ll find spacious, light-filled living areas thanks to vast floor-to-ceiling windows that frame the valley views. The ground floor is the social hub, with a welcoming lounge, a feature fireplace, a dining room, and a fully equipped kitchen—though catering packages with a private chef can also be arranged. Additional highlights include a wine cellar, games room, fully equipped gym, and a second sitting room, ensuring plenty of space for everyone.
Each of the seven bedrooms is tastefully decorated and has its own en-suite bathroom. Six boast super king-sized beds, while one can be set up as a twin or double. Two of the bedrooms are housed in the annexe, perfect for families or guests who’d like a little extra privacy.
Step outside to discover two hectares of gardens, olive groves, and vineyards. The heated infinity pool is the star attraction, complemented by numerous terraces, shaded dining spaces, and sun loungers ideal for lazy afternoons.
The villa’s concierge team can arrange extras such as truffle hunting, pizza-making classes, yoga, or guided tours. Though wonderfully peaceful, Villa Gaiole is close to picturesque Chianti villages and only 28km from Siena, making it an excellent base for exploring Tuscany’s art, food, and medieval history.
Villa Gaiole offers the perfect blend of tradition, elegance, and comfort for an unforgettable group holiday in Tuscany.
Features:
10-person capacity: main villa only14-person capacity: main villa and annexe
The Villa (800m2 over two floors)
Ground Floor- Living room with sofas, desk fireplace and TV- Games room with seating area, pool table and football table- Dining room with table seating 14- Fully-fitted kitchen with breakfast bar- Guest WC- Gym and Wine cellar- Internal courtyard- Bedroom with super king-sized double bed, seating area an en-suite bathroom with shower (accessible from the courtyard)
First Floor- Sitting room with bookshelves and TV- Bedroom with super king-sized double bed, seating area an en-suite bathroom with bath, double sink and WC- 2x bedroom with super king-sized double bed and en-suite bathroom with shower, sink and WC- Bedroom with twin beds or a super king-sized bed and en-suite bathroom with shower, sink and WC
Annexe- 2x bedroom with super king-sized double bed and en-suite bathroom with shower, sink and WC
Outside Grounds (20,000m2)
- Private heated swimming pool, with safety cover (12m x 6m, 1-3m deep) open approximately start of April- end of October- Two hectares of private grounds, olive groves and vineyards- Covered dining pergola- Al-fresco dining terrace- Wraparound terrace with outdoor sofas- Sun loungers and deck chairs - Barbecue- Pizza oven- Parking
Facilities
- Wi-Fi- Air-conditioning- Underfloor heating- Home office - TVs- Sound system- Film projector- Iron and ironing board - Gym equipment - Pool table- Football table- Board games and toys
Extra Sustainability Gems About the Property
The owners have installed solar panels and a wood pellet burner for hot water, as well as their our own fresh water well (natural and treated) which they encourage guests to use as opposed to buying plastic bottles of water.
Location:
Villa Gaiole boasts an enviable position overlooking the rolling hills of Chianti, immersing guests in one of Tuscany’s most iconic landscapes. Scenic walking trails, medieval hamlets, vineyards, and olive groves lie on the doorstep, perfect for countryside exploration at your own pace.
Wine enthusiasts can enjoy tastings at local farms or tours at nearby wineries, while food lovers will relish dining in rustic trattorias dotted throughout picturesque villages. Just 5km away, Gaiole in Chianti is a charming spot often ranked among Europe’s best places to live. Its rich history includes a number of castles—some now wineries, others open to the public—and a long tradition of ceramics. Lecchi in Chianti, 6km away, offers shops, cafés, and traditional eateries for an authentic experience.
Radda in Chianti, 12km away, provides a wider array of restaurants and shops. Once the headquarters of the Chianti League in the 15th century, this town enchants with winding medieval streets and historic landmarks such as the Palazzo dei Podestà and the Church of San Niccolò.
For a longer excursion, Siena lies just 28km from the villa. A medieval jewel, the city is packed with art galleries, museums, and iconic sights, including the Duomo di Siena and the Palazzo Pubblico. Its lively piazzas and rich café culture make it a must-see for visitors seeking Tuscany’s history and charm.
Terms & Conditions:
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An Accidental Damage Waiver of EUR 175 will be added to each booking to protect guests for up to EUR 2,500 in accidental damages at the villa. The waiver provides a limited damage cover in case of any damage to the property or its contents (except in the case of deliberate or reckless acts) up to the value of €2,500. It is essential to report any damage during your stay for the waiver to apply. For damages of a value which is above EUR 2,500 guests will be asked to pay based upon the value of the damage caused.
4.00 p.m. Check-in outside this time may be subject to an extra cost. Please enquire for more details.
10.00 a.m.
Yes.
Yes, with mid-week linen change for one-week stays.
Pets are not allowed.
Please note home security devices may be installed at the villa, please enquire for further information.
Please note that your booking will only be confirmed once we have checked availability with the owner or their property manager.
Please note that published rates are only valid for the current year. Any bookings for subsequent years will be on request only and correct rates will be confirmed at the time of booking.
Please note that the use of any external caterers and/or contractors is not permitted.
Flexible.
Included only for one-week stays. However, guests are required to leave the accommodation clean, tidy and in the same condition as on their arrival. Any extra cleaning, laundry, maintenance and/or rubbish disposal required will be charged against the security deposit.
Outside only.
7 nights from mid-June to mid-August. 4 nights between January to April and October to December. 5 nights in all other periods.
Estimated cost will be provided based on the week booked. Please enquire for exact amount, payable locally.
Included in peak months, and at an extra cost for the low season (October to April), payable locally. Please note that like all heated pools, pool heating and water temperature are reliant on weather and outside temperatures.
Italian Visitors Tax payable locally in cash (typically costs €1-€10 per person per night- please enquire if exact amount is required).
The pool is open approximately April to end-October. Please note that pool opening dates are subject to local weather conditions and pool maintenance requirements and that cooler months may not be suitable for swimming.
CIR: 052013CAV0037
CIN: IT052013B4ARQLP4UZ
Smoking - not allowed
