Luxury Feature Score - 7 / 10

accommodation> 10
accommodation> 5
accommodation> 5

Tennis Highlights

We have verified the following tennis facilties, equipement and services are present and that the playing surface is in good condition. 


How far away are all important everyday activities

Airport at Florence
Distance chart marker
1 hour
Distance chart marker
Airport at Pisa
Distance chart marker
1.5 hours
Distance chart marker
Motorway exit at San Donato
Distance chart marker
0.33 hour
Distance chart marker


Montesassi is a beautiful 400-hundred year-old farmhouse set on a hill top, offering air-conditioned bedrooms with mostly en suite bathrooms, plus included chef service for six breakfasts and four dinners during the week. It lies close to the vibrant Castellina In Chianti, half way between Florence and Siena, encompassed by warming natural scenery and quintessential Tuscan landscapes.

The old stone farmhouse is exposed to views of the rolling hills dotted with hamlets and villages within a countryside that has changed very little in the last five hundred years. The proud Florentine owners furnished the house in a very comfortable and welcoming style; there is a huge dining room when you don’t want to eat in the courtyard or under the loggia and many sitting rooms, offering lots of living space. There is a typically Tuscan kitchen that comes with a cook who prepares breakfast and evening meals (cost of ingredients excluded), whilst lunches can be arranged on order. 

In the huge garden you reach the private pool on a seperate lawned terace and complete with a loggia and dining table, a second loggia with a second dining table is set between the pool and the house. There is also a third loggia, with an outside living room, the ideal meeting point prior to dinner or for just for reading and relaxing out of the hot Tuscan Sun throughout the day. Perhaps the most popular feature form past clients has been the private professional-grade tennis court complete with floodlights, so avid players need not go without. 

Montesassi offers the perfect location from which to visit the Chianti as Tuscany, your half way between the two main cities of Florence and Siena with the superstrada/motorway that links the two cities about 15 minutes’ drive away. There is a fantastic restaurant, Osteria La Piazza within walking distance, about 400 meters away in the small hamlet called La Piazza, and a second restaurant that can be reached by foot in another hamlet but that a bit further away. 

Our Sales team knows the house well and they can answer any detailed questions you may have. The meals and any other service is all co-ordinated by our Concierge team, who will happy to discuss and organise any additional services such as shopping lists or cooking classes ahead of time, along with arranging the included chef services for your stay, ensuring it is a comfortable as possible. 



  • Airport Under 1 Hour
  • Private Tennis Court
  • Tennis Court Nearby
  • Pool
  • Gym
  • Outdoor Entertaining
  • Tennis Coach Available
  • Chef Available
  • House Keeping Available
  • Pet Friendly
  • WIFI
  • A/C
  • Parking
  • Bedding & Towels
  • Well Equipped Kitchen
  • Washer & Dryer
  • BBQ


Bedroom 1
King Bed (1)
Bedroom 2
Twin/Single Bed (2)
Bedroom 3
King Bed (1)
Bedroom 4
Queen Bed (1)
Bedroom 5
Queen Bed (1)


Tennis Court
  • Tennis Court - Private
  • Tennis Court - Clay

Included in this villa

This villa has the following servcies included in the rental price but additional services can be added from the add-on Servcies below this section.

Add on Services

These are additional verified  services that can be added to your rental pre and post arrival to enhance your experience.

Concierge Service

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