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Book Online or call VRBO Booking Assistance: 888-829-7076
Book Online or call VRBO Booking Assistance: 888-829-7076

Villa Montecastello, Rustic Luxury in the Heart of Tuscany

Bedrooms Studio
Property type villa
Minimum Stay 7 nights


About the property

Luxury Villa in the heart of Tuscany, Sleeps up to 18 guests

The Villa Montecastello is a luxury Agriturismo that has been immaculately renovated to offer its visitors an authentic and unique experience in Tuscany. Located one hour south of Florence, the Villa is surrounded by olive groves, with vineyards and nature reserves at its base. Originally a fortress, Villa Montecastello is located on an ancient road known as La Francigena in the town of Monteriggioni. Its hilltop location has been the stopover destination for many pilgrims, soldiers and merchants long before today’s owner, Jens Schmidt, decided to revive the art of hospitality in this 1000 year old hamlet between Siena and San Gimignano. The stunning views from the hilltop Villa and the silent surroundings of Montecastelli welcome our guests, while cultural and culinary destinations are reachable within a 15 minute drive. Located in the heart of our olive oil producing organic farm, the Villa is surrounded by the beauty of silver-green olive trees, mingling with the aromatic bushes of rosemary, lavender, jasmine and more.

Geared to the food and wine lover, Jens Schmidt, proprietor and architect of Villa Montecastello, will personally welcome you to his home and share his vast knowledge of local culture, food and Italian wine varietals. As a renowned wine expert, Jens can lead you through extensive wine tastings and will help arrange tours to wineries, private cooking classes and share insider secrets like where to find all the best antique and food markets.

In most seasons you can buy Tuscany’s best olive oil, Primo Olio, which is made right at our farm, enjoy fresh organic produce from our garden, sample Villa Montecastello's homemade prosciutto and salumi or gather fresh eggs from our own hens, all without leaving the Villa. You can book a privately catered dinner using our farm fresh ingredients, or schedule a pizza night cooking outdoors in our 1000 year old pizza oven. If you are tired of gourmet food and world class wines, you can always walk or mountain bike over the hill to the Astronave, our local trattoria, opt for a pizza at Indios in the neighboring town of Colle Val d’Elsa, or we can book a massage treatment for you in our own poolside facility.

From the back terrace of Montecastelli, you will have a view of the rolling mountains of the Montagnola, Tuscany’s green lung and nature reserve, offering well marked hiking trails where one rambles to discover rare birds, wild boars, porcupines, porcini mushrooms, wild orchids, chestnuts as well as the occasional truffle. We take care for making every detail of your stay memorable, so that Villa Montecastello will be the perfect home base for your Tuscan adventure.

At Villa Montecastello, we invite you to immerse yourself in the sights and sounds of nature, eat to your heart’s content, and soak in the sprawling views of the Tuscan countryside with a glass of Prosecco in hand. Relax by the pool or the fire place, when the season allows, and unwind with a stroll through our gardens. Each room in the Villa is uniquely furnished with the utmost attention to detail. All rooms offer luxury hand ironed linens, hand made olive oil soap, fresh cut flowers, air conditioning, coffee maker and ironing board. The Villa is laid out in a way that you can settle in comfortably and develop a relationship of your own to the place that we have come to love so much. Generously spaced kitchens and dining rooms, high speed internet connections, individual outdoor terraces with barbecue overlooking the sunset and San Gimignano in the distance, are some of the delights that await our guests. Villa Montecastello has many shared sitting areas both inside and out, a library filled with books about Italy, food and wine, as well as a professional chef ’s kitchen on site. Each room is filled with beautiful antiques and endless warmth and charm. Villa Montecastello can be privately reserved with accommodations available for up to 18 guests. Spread across two floors with a center courtyard, the Villa is made up of 9 guest rooms and 8 bathrooms, with 3 kitchens and 1 kitchenette, as well as common living room and sitting areas both inside and out. Villa Montecastello is the perfect location for large family holidays, small weddings, reunions, or a gathering of friends.

Please inquire if interested in renting smaller apartments. We have additional apartment rentals available that sleep minimum 2 guests or up to 10 guest.

More Details

Member since: 2014
Speaks: english, german, italian
Response time:
Within a few days
Response rate:
Calendar last updated:
July 9, 2018


Monteriggioni Villa Accommodation and Amenities

Property Type:
  • villa
House Rules:
  • Check-in: Flexible / Check-out: Flexible
  • Max. occupancy: 18
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Mountain View
  • Rural
  • 1 Bathroom
  • Bathroom - toilet , combination tub/shower , bidet
  • 8 bathrooms
  • Studio, Sleeps 18
  • 9 bedrooms of varying sizes, 7 bedrooms have private baths, 2 bedrooms have a large shared bathroom, sleeps up to 18 people.
  • limited accessibility
  • botanical garden
  • churches
  • festivals
  • health/beauty spa
  • restaurants
  • winery tours
Leisure Activities:
  • horseback riding
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • golf
  • hiking
  • hot air ballooning
  • mountain biking
  • swimming


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Car: recommended


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Tourism Tax (per person) $4.5

Please note, a €4.50 per guest tourism tax, required by the government, will be added to the bill at check out. Minimum stay is one week. Preferred day of arrival is Saturday. Villa is fully insulated and furbished with modern central heating and air conditioning. Additional services available upon request. Smaller apartments available upon special request to sleep between 2-10 guests.


Owner's Cancellation Policy

  • Canceled bookings will not receive a refund