Villa Gaiole

Discover the enchanting Villa Gaiole, where panoramic views, al fresco living, and endless activities await.

We had a wonderful time

Villa Gaiole - what a beautiful place. The photographs in the brochure online did not do it justice!We arrived in the early evening to see the moon reflecting on the infinity pool with the hills behind...

The house is beautifully appointed, the swim...

3 Reviews
Villa Gaiole Tuscany It Olivers Travels1

We had a wonderful time

Villa Gaiole - what a beautiful place. The photographs in the brochure online did not do it justice!We arrived in the early evening to see the moon reflecting on the infinity pool with the hills behind...

The house is beautifully appointed, the swim...

3 Reviews

Overview

Sleeps 10 - 14
7 Bedrooms
8 Bathrooms

Sustainable Collection

This property has been handpicked for its low environmental impact.

Property highlights

  • Private Pool
  • Air-Con
  • Wi-Fi/Internet
  • Gym/Fitness Room
Local Amenities
Nearest AirportFlorence
(66 km)
Nearest Airport 2Pisa/Perugia
(120-125km)
Nearest Airport 3Bologna
(160km)
Nearest Bar/PubGaiole in Chianti
(6 km)

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.

Oliver approved stamp

What Oliver loves...

  • With 360-degree views over Chianti’s rolling countryside, Villa Gaoile is the perfect base for exploring Tuscany’s beauty 
  • This stunning home is the ideal blend of old and new, as the 400-year-old property has been fully renovated throughout, using the finest materials
  • While staying here, you can visit charming villages and local farms on your doorstep or drive to some of Tuscany’s most amazing cities nearby
  • Ideal location for families, offering plenty of child-friendly facilities, including the pool with remote-controlled child safety cover.

What you should know

  • Pool heating is included in summer months but is an extra cost in low season. 
  • Guests can book extra services and experiences when staying here, such as truffle hunting walks, yoga classes, a private chef, catering packages, pizza making and photography courses 
  • As the home is set in Chianti’s rolling farmland, you will need a car in order to explore the nearby villages and towns 
  • You should be aware that two of the bedrooms are located in a separate annexe within the grounds.
  • The pool is is fenced with a remote control safety cover, however children should always be supervised when outdoors. 
  • Please note that stays booked under the 10 person rate, will only have access to the main villa, the annexe will be closed.

The Local Area

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4.7/5 Rated Excellent

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