Since 1982

Massimo 4

A villa for 4 with generous gardens : Rosia, Siena

Nice little touches

  • At the farther edge of Estate activity, Massimo has greater peace and privacy.
  • The two swimming pools mean there is one that is kept quiet for reading and relaxing while the second one - further away from the houses - is for fun and frolics.
  • The estate organises Pizza evenings and other communal activities which are held in the main estate square.

Good to know

  • Wireless internet available in all apartments, estate office, courtyard, furnished gardens and near swimming pools.
  • Pets are welcome, but only in Mid and Low seasons and never allowed around the swimming pools

In an earlier life Massimo was a Vinsanteria, a drying barn for the white grapes which produce Italy's famous dessert wine Vin Santo.

Sitting as it does at the far edge of activity in the Estate's central piazza, this house has greater peace and privacy and from all windows looks out to woodland views.

Massimo is listed under the following categories:

Accommodation

This detached house, with upper floor accommodation, was formerly a vinsanteria and dovecote and has retained its most charming features, including the delightful dovecote window.

External stone steps lead up to the large main room consisting of a dining area and a large living area with a soaring ceiling and a sofa and armchairs in front of an open fireplace.

Adjacent to the living room is an eat-in kitchen while off the dining area is a corridor leading to two bedrooms, a double and a twin, a newly renovated shower room and a bathroom. There is a garden at the front and a furnished patio shaded by a pergola at the far side of the house.

Features

Villa Details

  • Swimming Pool
  • Wifi
  • Free Parking
  • Fireplace
  • Insect Screens
  • Barbecue
  • Fans
  • Shared Swimming Pool

Bedrooms and Bathrooms

  • 1 Double Bedroom
  • 1 Twin Bedroom
  • 1 Bathroom With Shower
  • 1 Bathroom With Bathtub
  • 1 Hairdryer, More Available On Request

Kitchen equipment

  • Oven
  • Dishwasher
  • Italian And French Press Coffee Makers
  • Kettle
  • Home Grown Produce Available In The Farm Shop

Amenities

  • Wifi Internet
  • Telephone
  • Cd Player / Radio Available On Request
  • Washing Machine
  • Iron And Ironing Board
  • Tv/Dvd In Estate Rec Room
  • Baby Bed And High Chair Available On Request
  • Fans Available On Request

What's included

  • Final Cleaning Included
  • Pool Towels Provided (From Estate Office)
  • Firewood Provided
  • Central Heating

Extras

  • Arrival Groceries On Request
  • Cooking Lessons Available On Request Available On Request, For Adults And Children
  • Babysitting Available On Request
  • Children's Equipment Available On Request: Push Chair, Changing Mat, Bath, Stair Gate, Rocker, Babysitting
  • Extra Cleaning Available On Request
  • Ceramics And Art Courses For Adults And Children
  • Bicycles Can Be Arranged On Request
  • Transport And Tours Available On Request
  • This Property Is Subject To A €300 Cautionary Deposit On Card On Arrival (Authorisation Only)
  • Tourist Tax €1.50 Per Night Per Person Over 12, For Up To 6 Nights Only
  • Cot And High Chair €50 Per Week To Be Paid On Site
  • Extra Beds May Be Provided At €50 Per Bed Per Night

Outdoors

  • 2 Shared Swimming Pools, Both With Diving Boards And Sun Loungers. There Is A 'Quiet Pool' (16 X 6.5 M) Which Is Not Suitable For Children And A 'Family Pool' (15X7.5M, Depth Of .90- 2.50 M.) With A Shallow End Suitable For Children, With Parental Supervision. Pools Are Open From 1St June To 31St September.
  • Furnished Private Garden
  • Barbecue
  • Workshop And Conference Space In Estate Common Areas In The Granary - Large Space (14 X 28 M) Suitable For Art Courses Or Conferences.

Nearby Activities

Photos

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Reviews

“ Montestigliano villa Massimo ”

The setting is beautiful, very picturesque.

We stayed in Villa Massimo, clean and well appointed, there were four of us, myself my wife and our two boys; two in each bedroom, the boys beds were to be made up as singles but were set up as a double; this worked in our favour as we took the room without en-suite as the views were fantastic from the back bedroom.

When we booked the villa we looked at a large number of properties in the area, one of the reasons we chose Montestigliano was the listed activities, shown on their website. Unfortunately there was a large party celebrating their 10th wedding anniversary and as such only one of the two listed themed nights took place and no other activities were scheduled for our week, this was very disappointing and took the shine off of our stay, this would be a five star review if this had not happened.

We should have been notified that this was the case thus managing our expectations or allowing us to choose another location.

If we were going back to Tuscany I would definitely consider going back to Montestigliano, but I would check prior to booking; ensuring that there was nothing organised such as a wedding, anniversary or reunion to avoid disappointment

Would I recommend Montestigliano- yes, I would also recommend checking what’s on with them first , beautiful location, lovely setting nice accommodation and the one night that was organised was great fun

Julie and family staying in Massimo . Jun 2025

“ Our experience was magical ”

We stayed 5 weeks at Montestigliano this Fall. Our experience was magical. Our villa, Casa Massimo, was a delight - modern, spacious, well-equipped and comfortable. The grounds were beautiful, quiet and allowed spectacular views. Francisco, the manager/concierge could not have been more helpful. The location is convenient to Siena and there are nearby villages with outstanding restaurants and all the essentials one might need. We will be staying at Montestigliano again, without doubt!!

Mike staying in Casa Massimo . Sep 2023

“ Highly recommend this estate ”

Montestigliano was recommended to me by a friend, who said great things about her stay there in 2010. I looked at other sites in the general area, but nothing seemed better than her recommendation. The villa had everything we needed for a very comfortable week's stay in the Tuscan countryside, and bucket-loads of charm as well. The whole estate is picture-book perfect. There are numerous walking trails, including one to the nearest village where good coffee can be had. 2 pools (one designated for families) operate in the warmer months. We did not miss having a TV. Good WiFi kept us connected with the world (when we wanted to be). The estate is a short drive from the nearest small town for essential supplies, and less than 30 minutes' drive from Siena - a magical place that we went back to a number of times over the week. The opportunity to join other guests for a traditional Sienese dinner was fantastic. The estate's own olive oil is a wonderful product, which we made use of while we were there (and would have liked to take home, except our baggae limits wouldn't allow it!). Highly recommend this estate - I doubt you will have a better experience, and staff will do everything they can to make your stay memorable!

Anonymous guests, Australia staying in Massimo . Dec 2012

Where is Massimo ?

Getting here

  • Florence airport 1 hr 30 mins
  • Pisa airport 2hrs
  • Rome Fiumicino airport 2hrs 30 mins

Around Massimo

Guests on the estate share two swimming pools, one reserved for those who want peace and quiet, the other, further from the houses, for allowing free rein to summer holiday fun. Guests at all the properties may wander at will all over the estate. Part of the lands front the River Merse, which has excellent swimming and is protected for bathers by the Sienese authorities. The tiny village of Torri, with its famous monastery and striped cloisters is two minutes away by car, while there are pizzerie and restaurants within a few minutes' drive. A very important extra here is provided by the charming owners who will unobtrusively keep out of your way or happily go out of their way to help you, providing endless extra services if you require them, from sending faxes, arranging balloon trips, providing touring information, to translating at the doctor's.

During the summer concerts and exhibitions are often organised in the ancient granary, an extraordinary lofty space (14 X 28 m.) spanned by great arches laced with tie bars. This barn is also very suitable as studio space for art courses or conferences, and the rooms below, next to the estate offices, include a games room with billiards, TV, ping pong, a dining room, a catering kitchen and a small gift shop. The little restaurant provides delightful suppers twice a week.

Nearby Activities

  • Simple shop/restaurant in Orgia 2 kms
  • Shops, bars and restaurants in Rosia 5 kms
  • Siena 15 kms

Massimo: Sleeps 4
€ 1750 to 2274 per week

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Calendar for Massimo

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How to book

Is Massimo perfect for you?

For over 40 years, Invitation to Tuscany has personally selected and visited every villa we represent. Our team knows each property and its surroundings intimately - allowing us to help you choose the perfect home for your family or group, and to make your stay as memorable as the place itself.

How to Book

Check availability: View pricing and availability in the calendar above. To book online, click your desired arrival date, then your departure date. The calendar will grey out dates for stay lengths that aren't accepted—most villas book Saturday to Saturday, but many also allow shorter stays or flexible dates.

Need help choosing?

We visit our properties regularly and can provide firsthand advice based on your wishlist. Contact us and we'll help you select the best villa for your holiday. Secure your dates: We can hold your preferred dates for 48 hours while you confirm flights and coordinate with your group. To confirm, simply pay the 30% deposit. Your balance will be due 10 weeks before arrival.

Complimentary Concierge Service

Every booking includes our free concierge service to help make your stay special:

  • Up to 3 activity or restaurant bookings per stay
  • Local recommendations and insider knowledge
  • Standard check-in coordination
  • General travel assistance

Need more support? Our Concierge Plus (€300) provides dedicated planning support for guests requiring more activity bookings, larger group logistics, or special occasions. Please note that weddings and event planning do not fall under this. Request this when booking or as early as possible.

Flexible Booking Options

Easy cancellation: Add XCover to your booking for a full refund if you can't travel. You can add XCover anytime before paying your balance - just ask your agent. See our Booking Conditions and XCover for more information. Need to change dates? Let us know - we can often modify your booking rather than cancelling outright.

Worth Knowing

Tourist Tax: Many local administrations charge a tourist tax for rental accommodation, which varies by town. Charges typically range from €0.50 to €5 per person per night, with a maximum of 5-7 nights. Children are sometimes exempt. These charges are collected by property owners and paid directly to them.

Still Have Questions?

Call us for quick answers - we're here to help. You'll also find lots of useful information in our FAQ page . Haven't found the perfect villa yet? Browse our suggestions below!

CIN: IT052034B5XODYGVBO

Booking Notes

  • This property is subject to a €300 cautionary deposit on card on arrival (Authorisation only)
  • Tourist Tax €1.50 per night per person over 12, for up to 6 nights only
  • Cot and High Chair €50 per week to be paid on site.
  • Extra beds may be provided at €50 per bed per night