Cipressoin Province of Siena, Tuscany, Italy

12 Guests6 Bedrooms6 Bathrooms

This restored 13th-century villa, set within a 27-hectare Chianti wine estate, offers privacy, spacious interiors, and a private pool, all just seven miles from Siena.

Why we love this villa
Peaceful Location
Large Pool
Large Garden
Alfresco Dining
Historic Property
Beautifully Restored

Unique Features

  • · Beautiful 13th-century villa
  • · Stone construction with a watchtower
  • · Small art gallery with large windows
  • · Chianti wine produced on the premises

Situated within a 27-hectare wine-producing estate in the heart of Chianti, this meticulously restored 13th-century villa offers a tranquil Tuscan retreat. Its historic stone construction and distinctive watchtower provide a sense of timeless charm, while its central location near Siena makes it an ideal base for exploring the region's renowned medieval villages and cities.

The villa's exterior spaces are designed for relaxation and enjoyment. A spacious patio features a large outdoor dining table, perfect for al fresco meals, complemented by a barbecue grill. Guests can enjoy the private swimming pool, accessed via a paved path, surrounded by sun beds for lounging. Manicured gardens ensure complete privacy, and expansive grassy lawns offer ample space for families.

Inside, the villa's restoration preserved its original character, evident in the wood-beamed ceilings and stone walls. The ground floor features a spacious living room, where large arches define distinct areas. This level includes a dining area with seating for up to 12, a comfortable sitting area with sofas, and a secluded reading corner furnished with inviting leather armchairs. A separate main dining room on the west side can accommodate up to 20 guests. A fully equipped, modernized kitchen and a guest bathroom complete this floor.

The first floor hosts a living room equipped with air conditioning and a fireplace, offering two comfortable sofas and a dedicated space for aperitivo or wine tasting. On the second floor, another living room provides a comfortable sitting area with a fireplace and television, alongside a cozy space ideal for card games or quiet relaxation. The villa's distinctive tower, located on the third floor, houses a small art gallery with expansive windows that frame the Chianti landscape.

The villa accommodates up to 12 guests across six double bedrooms, each featuring air conditioning. All six bathrooms are equipped with hair dryers. The first floor includes four double bedrooms, each with either an en-suite or private bathroom with a shower. The second floor offers one double room with a private bathroom featuring a tub and shower. The final double bedroom, located on the third floor, includes an en-suite bathroom with a shower.

Guests benefit from a range of included services: electricity, air conditioning, water, final cleaning, Wi-Fi internet access, and weekly garden and pool maintenance. For stays between May 23rd and August 21st, housekeeping service is provided two days a week for up to four hours (excluding Sundays); for the remainder of the year, a midweek four-hour housekeeping service is included, along with a mid-week change of towels. Additional services such as heating, extra housekeeping, linen changes, cook service (provided by villa management only), and personal laundry are available at an additional cost. A dedicated parking space is provided, and caretakers reside in a separate annex on the estate, ensuring guest privacy.

Amenities

  • Air Conditioning
  • WiFi
  • Fully Equipped Kitchen
  • Outdoor Dining

Where you'll sleep

  • Double Bed
  • Air Conditioning
  • Private Bathroom with Bathtub and Shower

Bedroom 5

Second Floor
  • Double Bed
  • Air Conditioning
  • Ensuite Bathroom with Shower

Bedroom 6

Third Floor

Services Included

Welcome Amenities
Welcome Amenities
Housekeeping
Housekeeping
24/7 Support
24/7 Support
Towel Change
Towel Change
Pool Cleaning
Pool Cleaning
Gardening
Gardening
End of Stay Cleaning
End of Stay Cleaning

Suited For

  • Large Groups
  • Groups
  • Family
  • Children
  • Wine Enthusiasts
  • History & Culture
  • Active
  • City Escapes
  • Walking & Hiking

Setting and View

  • Mountain Views
  • Countryside
  • Nature Views
  • Close to Town
  • Country Views
  • Panoramic Views
  • Vineyard Views

Nearest Airport

· Florence Peretola (FLR) - 1 h 22 min

Nearest Town

· Nearest serviced town: 10 min
· Siena 36 min

Essential Information

Check-in:

From between 5:00 pm – 7:00 pm

Check-out:

by 9:00 am

House rules

Staff & Services
No third-party suppliers allowed: the services will be provided by the villa management and in-house staff.

Included

Housekeeping
For stays between May 23 and Aug 21: Housekeeping service 2 days/week for up to 4 hours (except Sun); for the rest of the year: midweek 4 hours housekeeping service.
Towel Change
Mid-week change of towels.
Gardening
Garden and pool maintenance once a week.

Not Included

Utilities
Heating charges, if used: €100 per day.
Housekeeping
Extra housekeeping service: €30 per hour/per staff member.
Additional Bedding
Additional change of towels: €8 per set/per person/per change.
Additional Bedding
Additional bed linen change: €10 per bed/per change.
Tourist Tax
Visitor’s tax: 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.
Food and Sundries
Cost of food and beverages.
Staff & Services
Personal laundry and ironing service: €30 per hour.
Porter Service
Porter service with delivery of suitcases to the rooms (advanced notice required): €8 per suitcase.

Additional Information

Good To Know
Caretakers live in a separate annex on the estate – guests’ privacy is guaranteed.

Rates

Date Range:Nightly Rate:Min Nights:
10 Jan 202610 Apr 2026$2,035.407+ nights
11 Apr 202622 May 2026$2,646.787+ nights
23 May 202621 Aug 2026$2,877.527+ nights
22 Aug 202616 Oct 2026$2,540.677+ nights
17 Oct 202611 Dec 2026$2,035.407+ nights
12 Dec 20262 Jan 2027$2,396.677+ nights
3 Jan 202730 Mar 2027$2,877.527+ nights

Additional Fees & Deposits

Utilities Fee$117.90 /day
Damage Insurance$293.56
Security Deposit (refundable)$1,768.45
Please note: Rates are subject to change without prior notice.

Elevate Your Experience

Shortly after booking, your personal concierge will be in touch to help you plan the finer details that will make your stay unforgettable.

Daily Tidy & Refresh

Private Vehicle Hire

Nanny & Childminding

Child Toy & Equipment Rental

In-Villa Bartender

Curated Excursions

Dining Experiences

Grocery Delivery

Private Chef

Yacht & Boat Excursions

Butler Service

Celebration Planning

Sports Equipment Rental

Airport & Local Transfers

In-Villa Spa Treatments

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