Europe / Italy / Tuscany

Chianti has much to offer to those interested in its extraordinary wine; and, to all visitors, it also offers its exceptional food and natural beauty.

up to 6
up to 12
from 7
Min. Nights


Thanks to its central location, this Tuscan region is a perfect starting point for exploring medieval hilltop villages as well as the historical cities of Florence, Siena and Lucca. Set among 27 hectares of one of Chianti’s many outstanding wine-producing estates is Cipresso, a beautiful 13th century villa located approximately 7 miles from Siena. Now restored, the property offers comfort, peace and privacy. Its stone construction, along with its watchtower, exudes the typical character and charm of Tuscany. The villa’s spacious interiors are ideal for large groups who want to gather or have privacy when needed. What better way is there to end the day than by enjoying a glass of Chianti wine that was produced right here on the premises?

The spacious grassy lawns of the estate are perfect for families with children. The location is ideal for wine-lovers as it is a great starting point for trips to Chianti Classico and its charming villages of Gaiole, Castellina, and the Castle of Brolio, which are within 10 miles from the villa.


Ground Floor

Much attention has been dedicated to the interiors of the villa during the restoration to maintain the original structure.
This care is visible in the wood beamed ceilings, the stone walls, and especially on the ground floor where big arches frame the different areas of the spacious living room. This floor also includes a dining area with a large table that can seat up to 12 guests, a sitting area with comfortable sofas, and a sunk-in reading corner with its inviting leather armchairs. The main dining room, on the west side of this floor, can accommodate up to 20 guests. A spacious, well-appointed fully equipped kitchen and a guest bathroom complete this floor.

First Floor

On the first floor is an air conditioned living room, fireplace, two comfortable sofas and an area dedicated to aperitivo or wine tasting.

Second Floor

On the second floor is a living room featuring a comfortable sitting area with fireplace and TV. There is also a cozy space for relaxing and playing cards among friends.

Third Floor

The third floor is the tower that houses a small art gallery with large windows overlooking the beautiful Chianti landscape.

Outside Features

The villa patio features a large outdoor dining table, perfect for shady relaxing and informal dining, and there is also a BBQ grill and outdoor cooking area to prepare delicious local-food feasts. The private large swimming pool is reachable through a paved path and there are sun beds around the pool to enjoy hours of sunbathing. The pool has a ladder on one side. Manicured gardens surround the property for complete privacy.


6 Bedrooms, 6 Bathrooms

Sleeps 12 Guests

  • Wi-Fi
  • Washer
  • Hair Dryer
  • Dishwasher
  • Dining Area
  • Fully Equipped Kitchen
  • Fireplace
  • Mountain View
  • Parking Space
  • Al Fresco Dining
  • Satellite TV
  • Playstation
  • TV
  • Stereo


Bedroom Details

Bedroom 1 (First Floor): Double bedroom with en-suite bathroom with shower
Bedroom 2 (First Floor): Double bedroom with private bathroom with shower
Bedroom 3 (First Floor): Double bedroom with en-suite bathroom with shower
Bedroom 4 (First Floor): Double bedroom with private bathroom with shower
Bedroom 5 (Second Floor): Double room with a private bathroom with tub/shower
Bedroom 6 (Third Floor): Double bedroom with en-suite bathroom with shower
All bedrooms have A/C except the children’s bedroom with bunk beds (north exposure); all bathrooms are provided with hair dryers

Pool Details

Large, private swimming pool

Staff and Services

Final cleaning
For stays between May 25 and Aug 25: Housekeeping service 2 days/week for up to 4 hours (except Sun); for the rest of the year: Midweek 4 hours housekeeping service.
Mid-week change of towels
Weekly garden and pool maintenance

Staff and Services (at Additional Cost)

Extra housekeeping service
Additional change of towels
Additional bed linen change
Laundry and ironing service
Cook service – No third-party suppliers allowed: the services will be provided by the villa management and in-house staff
Cost of food and beverages
Porter service with delivery of suitcases to the rooms (advance notice required)

Location Details

Nearest Airport: Florence Peretola 1 h 22 min
Nearest serviced town: 10 min
Nearest major city: Siena 36 min

Villa Notes

Electricity, A/C and water are included
Wi-Fi Interned included
Caretakers live in a separate annex on the estate – guests’ privacy is guaranteed
Check-in: between 5:00 pm - 7:00 pm
Check-out: before/by 9:00 am
All the above services must be paid locally, prior to departure unless otherwise arranged

Rates and Availability

Tax Service Charge Details*
The Italian government might require the payment of a Visitor’s Tax (approximately €1.50 – €6.00 per person, per day, depending on the location) and may be applied for the first ten days in the destination. This tax is payable locally, in Euro cash.
Heating charges, if used: €100 per day
Security Deposit Details
€1,500 pre-collected
Accidental Damage Waiver
A €149 Accidental Damage Waiver applies to every reservation.
Minimum Stay Details
1 Week - Saturday to Saturday rentals.
Check-In Times
Check in: 4:00 PM - Check out: 9:00 AM

Exclusive Offers

Book by now and get 20% off regular villa rates in 2024.

Valid for new bookings made now to 12/15/2024 for travel during remaining available weeks in 2024. 7 Night minimum booking required. Subject to availability and may not be combinable with other offers. Additional restrictions may apply; please call for full details.



The villa and the owner and staff exceeded all of our expectations. We had a wonderful time, and Pino (the owner) was a most gracious host. We found the villa to be perfect for gatherings of our large group, but also provided many areas for more private gatherings. The pool was large and refreshing. The concierge (Daria) arranged for a breakfast each morning for the group, which was provided by the staff at the villa - a great way to start the day. We also had a dinner cooked for us at the villa one night, which was a lot of fun. A special treat was the two cases of fantastic Chianti Classico made by our host, which we purchased for a very low price. Pino and his son always greeted us with a smile. A fantastic week. - Michael C.

Villa information may change without notice and should be confirmed with our villa rental specialists.