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Villa Il Masseto

Gaiole in Chianti - Siena and Chianti

8 4 3 Without Pool
Villa Il Masseto is a traditional Tuscan villa, peacefully located on the edge of Gaiole in Chianti, bordered by forest and just a 3-minute walk from the center. Perched on a gentle hill, it offers stunning views over the town’s church tower and rooftops. The distant chimes of the bells add an unmistakably Tuscan ambiance to your stay. It’s a perfect retreat for families or groups of friends looking to relax and enjoy the region’s beauty.

Despite its peaceful, semi-rural location, Villa Il Masseto is within walking distance of restaurants, wineries, and a COOP supermarket in Gaiole. The picturesque Chianti towns of Radda, Castellina, and Greve are nearby, while Siena, Florence, San Gimignano, and Arezzo are all easily reachable for day trips.

Guests can enjoy a large, well-tended garden with mature shade trees and a hot tub, while the outdoor shower provides added convenience after a soak or a warm day in the sun. Three spacious covered balconies provide inviting spots for al fresco dining throughout the day. The property also includes two sheltered parking spaces.

The villa occupies the entire first floor, while the ground floor remains locked and unoccupied. The house is built from local stone and features bright, airy living spaces, high ceilings, a small library, and multiple seating areas, all thoughtfully styled to create a warm, welcoming atmosphere. 

Villa Il Masseto is an ideal base from which to discover the beauty of Chianti Classico, a place where vineyards, culture, and authentic Tuscan life come together.

First Floor

Library

Bookshelves, chairs.

Lounge
Sofa, armchair, TV, chairs, side tables, chest of drawers, fireplace (decoration only), table, air-conditioning, French door to balcony, balcony with table and chairs.

Dining Room
Welsh dresser, table, chairs, French door to balcony, air-conditioning.

Kitchen
Fully equipped kitchen, gas hob, fridge/freezer, side table, TV, table, chairs, air-conditioning, mosquito net.

Bedroom 1
Queen-size double bed (can't be converted into twin beds), bedside tables, desk, chair, chest of drawers, wardrobe, fan, mosquito net.

Bathroom
Shower, double sink, bidet, WC.

Bedroom 2
Queen-size double bed (can't be converted into twin beds), bedside tables, chairs, wardrobe, desk, chair, chest of drawers, fan, French door to balcony.

Bedroom 3
Queen-size double bed (can't be converted into twin beds), bedside tables, chairs, wardrobe, desk, chair, chest of drawers, air-conditioning, mosquito screen.

En-suite Bathroom
Shower, double sink, bidet, WC, washing machine.

Second Floor

Bedroom 4
Double bed (can't be converted into twin beds), bedside tables, wardrobe, mosquito net, air-conditioning, ceiling fan. 

En-suite Bathroom
Shower, sink, WC.

Hot Tub
Opening times: May to October

Private Pool
There is no pool

Price & Availability

Date Ranges

7 night price

20 Jun 2026 - 29 Aug 2026

2,550 Euro

29 Aug 2026 - 10 Oct 2026

1,915 Euro

10 Oct 2026 - 7 Nov 2026

1,915 Euro

7 Nov 2026 - 19 Dec 2026

1,915 Euro

19 Dec 2026 - 2 Jan 2027

1,915 Euro

2 Jan 2027 - 9 Jan 2027

1,915 Euro

9 Jan 2027 - 20 Mar 2027

1,915 Euro

20 Mar 2027 - 22 May 2027

1,915 Euro

22 May 2027 - 26 Jun 2027

1,915 Euro

26 Jun 2027 - 4 Sep 2027

2,550 Euro

4 Sep 2027 - 16 Oct 2027

1,915 Euro

16 Oct 2027 - 13 Nov 2027

1,915 Euro

13 Nov 2027 - 18 Dec 2027

1,915 Euro

18 Dec 2027 - 1 Jan 2028

1,915 Euro

Villa Facilities

Dog Friendly
Flexible dates
Air-conditioning
Washing Machine
Internet

Villa Floor Plans

Good To Know

Usage to pay on-site: Heating Villa, Air Conditioning, Heating Hot Tub
Tourist tax: 2.00 € per person, per night for the first 7 nights, some exemptions apply.
Dog up to 30kg: stay for free
Meet and greet: Arrival time is 16:00 - 19:00. Departure time is before 10:00. 

Villa Location

Distance

Airports:

Distances and driving time

  • Airport Florence: 83km - 1h 14m
  • Airport Perugia: 129km - 1h 37m
  • Airport Pisa: 145km - 1h 53m

Towns with Amenities:

Distances and driving time

  • Gaiole in Chianti: 0km - 0h 02m
  • Castagnoli : 5km - 0h 09m
  • Radda in Chianti: 8km - 0h 15m

Guest Reviews

Annalee

August 8, 2026

Group of friends

Germany

Perfect spot for a family vacation - everyone had their own space thanks to how the house is laid out, Gaiole center is walkable and also plenty of opportunities for walking and hiking in nature around the place. Lovely space and very comfortable. Thanks for a great stay!

To Tuscany team comments for this review:

Thank you very much for your wonderful 5-star review. We are delighted to hear that Villa Il Masseto was the perfect villa for your Tuscan getaway. It’s great to know that the layout worked well for your group and that you enjoyed visiting Gaiole on foot as well as hiking in the stunning surroundings. We hope to welcome you to Tuscany again!