Our family of 12 (including six children ages 1, 3, 3, 3, 7, and 9) stayed at Villa Leonardo over Thanksgiving holiday. We had an absolutely amazing week. Instrumental to the success of our stay was this amazing property, caretaker Margarita & her partner and our chef which made every evening effortless and delicious. The caretakers surprised us with fresh & tasty pastries, recommendations, light cleaning and even installed a baby gate for our big baby Alexander who they affectionately nicknamed Ale- a nickname he still responds to today.
I can’t wait to make this vacation a tradition. Highly recommend! - Vanessa B. G.
Leonardo
Europe / Italy / Tuscany
Villa Leonardo is a beautiful, private 12-acre estate tucked away in Chianti, the heart of Tuscany, between Florence and Siena.
up to 6
Bedrooms
up to 12
Guests
6
Bathrooms
Min. Nights
Upon Request
Overview
Located half way between Montespertoli and San Casciano Val di Pesa, the villa is 40 minutes away from Florence. The ultimate in privacy and independence, both the exterior and interiors of this fine old farmhouse have been restored to a very high standard by its owner. The house is beautifully decorated throughout with terracotta floors, whitewashed walls and beamed ceilings. Villa Leonardo is a refined and elegant estate, ideal for an extended family or a group of friends looking for spacious accommodations, comfort, privacy and stunning views. Even when occupied by 12 people, the house feels spacious yet cozy. It blends country charm with simple elegance.
Living Spaces
The living areas on the ground floor are colorful and furnished with high-quality fabrics, antiques, fine custom linens and tableware. An elegant dining room has direct access to the garden/porch. The living room has an open fireplace, ample sofas and a large smart TV. The study offers a quiet office or reading space and a library.
Outdoor Features
The house is accessed by a private dirt road (half a mile) and surrounded by an extensive and well-tended garden that rolls gently downward from the house towards the swimming pool, which is situated among sloping green lawns and fruit trees. Near the swimming pool (12 x 6 meters) and around the garden and terraces, there is an abundance of outdoor furniture, teak pool furniture, wrought-iron and rattan lounges, benches and chairs, marble tables, and sun umbrellas for shade.
Special Characteristics
The property enjoys a spectacular view of a 10th-century castle and a panorama of the Chianti countryside with its rolling hills, vineyards, olive groves, cypresses and distant farmland. The estate is comprised of 350 olive trees, over 100 walnut trees, a small river delineating its southern boundaries and several acres of forest providing wonderful shade in the summer.
Features
6 Bedrooms, 6 Bathrooms
Sleeps 12 Guests
A/C in bedrooms
Wi-Fi
Fenced private swimming pool (12m x 6m)
Washer
Dryer
Hair dryers in all bathrooms
Refrigerator x 2
Dishwasher
Fully Equipped Kitchen
Dining Area
Mountain View
Window screens
Heating
Outdoor Furniture
Fireplace
Al Fresco Dining
Private Parking
Remote-controlled gate entrance
Stereo
Smart TV with streaming apps
Printer
Details
Bedroom Details
Bedroom 1 (Ground Floor): Queen/twin bedroom with private adjacent bathroom with shower.
Bedroom 2 (Ground Floor): Queen/twin bedroom, with independent entrance and en suite bathroom with shower.
Bedroom 3 (First Floor): King bedroom with en suite bathroom with double sink, tub and walk-in shower.
Bedroom 4 (First Floor): King bedroom with en suite bathroom with shower and skylight window.
Bedroom 5 (First Floor): Twin/queen bedroom with en suite bathroom with shower.
Bedroom 6 (First Floor): Twin/queen bedroom with en suite bathroom with tub with handheld shower.
Pool Details
Swimming pool 12x6 meters
The pool open from mid-May until mid-September, weather permitting.
Staff and Services
Final cleaning included
Garden and pool maintenance
Staff and Services (at Additional Cost)
Housekeeping service
Change of linens
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
Pre-stock grocery service
All the above services must be paid locally, prior to departure, unless otherwise arranged
Location Details
Nearest Airport: Peretola Florence Airport 34 min
Florence - 40 minutes
Greve in Chianti - 50 minutes
Siena - 1 hour
San Gimignano - 40 minutes
Fornacette - 6 minutes
Villa Notes
Electricity, heating, and water are included
Wi-Fi internet connection included
Check-in: between 4:00 pm - 7:00 pm
Check-out: before/by 10:00 am
Caretaker lives on the premises, in separate quarters. Guests' privacy is guaranteed.
Access is via a dirt road, and for a more comfortable arrival, vehicles with sufficient ground clearance are recommended.
Rates
| Travel Dates | Bedrooms | Min. Night Stay | Nightly Rates |
|---|---|---|---|
|
January 17, 2026 - April 03, 2026
|
6 | 7 | $ 1,117 * |
|
April 04, 2026 - May 29, 2026
|
6 | 7 | $ 1,506 * |
|
May 30, 2026 - October 02, 2026
|
6 | 7 | $ 1,652 * |
|
October 03, 2026 - October 30, 2026
|
6 | 7 | $ 1,506 * |
|
October 31, 2026 - December 11, 2026
|
6 | 7 | $ 1,264 * |
|
December 12, 2026 - January 02, 2027
|
6 | 7 | $ 1,385 * |
| USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your vacation specialist at time of booking. | |||
Tax Service Charge Details *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.Telephone charges extra | |||
Security Deposit Details€2,000 - pre-collected | |||
Minimum Stay Details1 Week - Saturday to Saturday rentals. Minimum night stay may vary by villa. Please contact a villa specialist to confirm. | |||
Accidental Damage WaiverA €249 Accidental Damage Waiver applies to every reservation. | |||
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Location
Reviews
Our stay at Leonardo was the highlight of our trip. The caretakers, Margie and her husband were wonderful. - Patty
Villa information may change without notice and should be confirmed with our vacation specialist.
