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.
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.
Amenities
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
- Private Parking
- Al Fresco Dining
- Fireplace
- Outdoor Furniture
- Heating
- Window screens
- 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.
Exclusive Offers
Your next escape, rewarded. The world's most extraordinary villas deserve to be experienced — and now, they come with a return. Receive up to $1,000 cashback, paid upon deposit, simply for booking the trip you've been dreaming of.
Amount based on the booking value:
$15,000 – $49,999 = $500 Cashback
$50,000 – $100,000 = $750 Cashback
$100,001+ = $1,000 Cashback
Offer valid for new bookings made between 5/22/26 - 6/13/26. Amount is based on the base villa cost only (excluding taxes and fees). Minimum booking value applies ($5,000.00).Cash back will be paid in a Villas of Distinction Visa® Prepaid Card upon deposit. Villas of Distinction Visa® Prepaid Card is issued by MetaBank®, N.A., Member FDIC, pursuant to a license from Visa U.S.A. Inc. No cash access or recurring payments. Can be used everywhere Visa debit cards are accepted. Card valid for up to 12 months; unused funds will forfeit after the valid thru date. Card terms and conditions apply. Offer is valid for direct clients OR travel advisors’ clients. The Villas of Distinction Prepaid Card will be mailed directly to the direct client OR travel advisors’ client within 30 days of deposit. Client mailing address must be provided. May not be combinable with other offers. All offers are subject to availability and may not apply to all villas or travel dates. Other restrictions may apply; please call for full details.
Telephone charges extra
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 villa rental specialists.