La Madonnina

Tuscany , Italy

  • 2-4
  • 1-2
  • 1
  • Two delightful 2-bedroom apartments, one studio cottage
  • Stunning views
  • Beautiful gardens
  • Local bar and grocery shop 10-minute stroll
  • Castiglion Fiorentino 10-minute drive

At the end of the drive leading up to this simple and atmospheric building is the 17th-century shrine to ‘The Little Mary’ who gave the house its name. Visitors were still making offerings there up until the end of the 1980s, but now, in this beautiful landscape of vineyards, olive groves and the Val di Chio, a different kind of pilgrimage is in order. Once a modest agriturismo, La Madonnina was chosen for its unpretentious charm and the warmth of the welcome; a stay here restores calm and invites exploration in equal measure.

The two cleverly laid out two-bedroom apartments (Gli Avi and La Nonna) include well-equipped kitchens making this small, peaceful retreat ideal for families and couples who like to retain a little independence. In addition there is also La Capannina, a charming studio cottage set apart from the main building with its own al fresco dining area. The décor throughout La Madonnina has a rustic authenticity typical of the region – exposed beams and brickwork offset by white painted walls – very much in keeping with the relaxed atmosphere and homely feel created by the owners Maria and Rinaldo.

Gli Avi is the larger of the two apartments, with a private terrace to match, but the stunning views here are for everyone, as are the shared swimming pool and lovingly tended gardens, where Rinaldo’s signature sculptures can be found dotted about, adding to the harmonious sense of pleasure as you unwind and drink in the serene beauty of the place.

Maria’s generosity of spirit is immediately apparent and her culinary flair is on hand should you wish to request breakfast or an evening meal – lovingly created with seasonal produce and paid for locally. Or if you'd like to learn the art of Italian cuisine yourself, you can even take a cookery course.

La Madonnina is wonderfully off-the-beaten-track: a place to embrace Tuscan life at its rural best and enjoy the genuine hospitality of its people. Maria and Rinaldo are a mine of local information and whilst their English is a touch inventive on occasion, very little is lost in translation thanks to their infectious enthusiasm and passion for their beautiful surroundings. And if you’re keen to embrace La Dolce Vita and try a few words of Italian in return, your efforts will be met with the utmost joy and respect.


The local area

The nearest local bar and a basic grocery store are just a 600m stroll away. For everything else, there’s Castiglion Fiorentino, a ten-minute drive away or 6km along a footpath and cycle track. This impressive Renaissance town rises above the Valdichiana Plain and has banks, shops and chemists, as well as atmospheric bars, traditional squares, open-air restaurants and culture aplenty – the old Gothic church of San Francesco and the Madonna della Consolazione temple are worth a visit. The town also hosts a number of lively festivals, including an eight-day medieval festival at the end of May/beginning of June, complete with traditional food, costumes, parades and fireworks.

For walkers, this region is flanked on one side by the Pratomagno Mountains and on the other by the attractive Alpe di Catenia and, being near the Umbria-Tuscany border, you’re well placed to explore both regions. 

For day trips, Florence is easily accessible by train and Cortona, Lake Trasimeno and Perugia are also within easy reach.

Explore our pre-bookable experiences in Tuscany




  • Two 2-bedroom apartments (sleep 2-4)
  • Studio cottage (sleeps 2)

Gli Avi

  • 2-bedroom apartment
  • Open-plan sitting/dining/kitchen area with open fireplace
  • Kitchen includes hob, gas oven, fridge; French door leads to large terrace for dining al fresco
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

La Nonna

  • 2-bedroom apartment
  • Open-plan sitting/dining/kitchen area with open fire place
  • Kitchen includes hob, gas oven, fridge; French door opens to small terrace
  • Stairs lead up to double bedroom
  • Twin bedroom (can be configured into a double if required)
  • Shower room

The Cottage

  • Studio cottage
  • Double bedroom with en-suite shower room
  • Outdoor seating/dining area


  • Simpson Travel telephone representative
  • Air-conditioned bedrooms
  • Complimentary WiFi
  • Tea and coffee making facilities
  • Hairdryer
  • Laundry room (first wash is complimentary, thereafter payable locally)
  • Simpson Travel pool towels
  • Shared swimming pool 6m x 12m (depth 1.40m throughout)
  • In Italy, a daily tourist tax applies for the first week of your stay only, which means that an average of €1 per person (12+ years) may be charged. This should be paid in cash to the owner during your stay.
  • The swimming pool will be closed from 30 September until the end of the season.
  • Optional central heating €30/day, payable locally
  • Optional firewood €10/basket, payable locally

Simpson family extras

  • Complimentary cot and highchair available
  • Car seats and booster seats can be provided at a supplement, subject to availability
  • To pre-book any of our family extras please call 020 8392 5747


  • All properties with WiFi are able to support basic functionality such as web browsing and checking emails. We aim to offer an uninterrupted service but sometimes due to factors beyond our control reliability can be affected.

Access times

  • Check in time – 4pm - 8pm
  • Check out time – 10am


  • Breakfast available on request – Italian and continental 
  • Dinner available, pre-booking essential (minimum 2 guests, 4 courses, €30/person) – Menu
  • Vegetarian options available (pre-booking essential and we regret there are no gluten-free options at this time)
  • Meals cooked using home-produced olive oil and served with fresh bread and home-produced wine
  • Dinners not available on Sunday
  • All meals are on request and payable locally 


  • Localitá Santa Cristina (bar and grocery shop) 10min walk
  • Castiglion Fiorentino (shops/restaurants) 10min drive
  • Cortona 30min drive
  • Arezzo 40min drive
  • Siena 1hr 10min drive
  • Florence 1hr 30min drive
  • Pisa airport 2hr 15min drive
  • Rome Fiumicino airport 2hr 30min drive


This property is priced on an accommodation-only basis. To view details of recommended flights please click here.

Car hire

We are happy to arrange your car hire in Italy; please click here to view options and prices. All hire cars booked with us include: 

  • Fully inclusive insurance, with zero excess*
  • Free additional driver

For further information regarding travel arrangements click here.

* For this particular destination, the undercarriage is not included in the cover.



Thank you very much Maria and Rinaldo. We have had a great week. Visited Arezzo, Cortona and Assisi with a cycling day around Montepulciano. Thank you for a lovely meal and surroundings and pool to enjoy the warm early October weather.

Fred and Emma, October 2023

We had a lovely stay in La Nonna and Maria couldn’t have been more welcoming. She cooked for us (twice) and both meals were very delicious. The house was perfect for us and a good base for sightseeing the main towns/cities. Thank you so much.

June and Michael, September 2023

Lovely week in this beautiful and quiet place. It was a great base from which to explore Siena, Florence and Arezzo but also to spend lazy days locally. Maria was most welcoming and friendly – cooking a delicious supper on our arrival. Thank you.

Sara and Tim, September 2023

Our stay has felt like a real home from home. What a lovely apartment with everything we need.

Anita and Chris, September 2023

A wonderful stay in this delightful villa Tuscany. Maria is a wonderful host and cook.

Mr Michael Birks, September 2023

We’ve had such a lovely stay in La Nonna and have been looked after so well by Maria. We have two young children with us so to be able to have the flexibility of our own kitchen, the balcony to relax and the pool, have made this a truly relaxing home to return to at the end of a busy day exploring. Our children have especially loved ‘visiting’ Maria, who has been most obliging, as well as Eva and Jack, the doggies! Lovely meals made by Maria (probably the best ones we had!). Overall a truly wonderful stay and one we won’t forget.

Jenna, Greg, Oliver and Eva, July 2023

Have spent a lovely week in Tuscany at La Madonnina. Castiglion Fiorentino and Cortona are both beautiful and a visit to Siena is well worth it, also Florence and taking the train there is easy. All in all a wonderful area of Italy with excellent food and wine, amazing views and countryside and stunning medieval towns and cities. Thank you to Maria and Rinaldo for providing a beautiful base from which to explore the region. The eggs were delicious and we shall definitely miss the view from the balcony.

Helen & Paul, June 2023

What a lovely stay we have enjoyed – so peaceful and the garden is a joy to sit in with fragrant flowers all around, views of distant hills and terraces. We completely relaxed and enjoyed a few days out to Montepulciano, lovely hilltop town, and Arezzo – lovely antique shops and parks. Altogether, great times.

Jane and Phil, June 2023

Maria and Rinaldo made us feel part of the family. Maria played hide and seek with our daughters, showed us their dogs, chickens and garden. Rinaldo took our young daughter on a tractor ride and they spent the next week talking about what a wonderful place to call home for two short weeks. We have been taught nursery songs from Maria, been cooked the most delicious dinner and will spend all our next vacations comparing them to this unbeatable magical dream of a vacation. Our hearts are filled with love and joy after these two weeks. We can’t wait to return to Maria and Rinaldo – our Tuscan family.

Diana, Jacob, Darcy & Charlotte, May 2023

Many thanks to Maria and Rinaldo for making our stay at their beautiful villa – such a joy. Not only did we spend time with our grandchildren around the pool, but we also used La Madonnina as our launch pad to Florence and Siena. They treated us like family. Maria showed the little girls her chickens and gave us eggs for breakfast. Rinaldo gave them a tractor ride. Like everyone else has said, the views from the villa are breath-taking! We will recommend La Madonnina to our friends for future vacations.

Becky & Andy, May 2023

A repeat visit to Maria and Rinaldo at La Madonnina - and another relaxing, homely stay in a lovely part of Tuscany. Strongly suspect we'll return again :-).

Mark Sims, October 2022

La Madonnina was recommended by a friend. We so appreciated her sharing this little gem. A perfect opportunity to explore rural Tuscany, enjoy Maria’s food and simply relax. Amanda our local concierge, introduced herself by email and when advice was sought she was extremely helpful.

Rachel & David, June 2022

We have so enjoyed this beautiful and tranquil valley and region. Maria and Rinaldo provide plenty of advice and warm hospitality. You have to try a cooking lesson and then enjoy your efforts. We enjoyed several meals out – you don’t really have to venture beyond Castiglione Fiorentino but we also made it to Cortona and Siena and had great days at both. The local winery offers a very lovely tour – however, nothing compares with the €2 per litre red wine M&R get from the local farmer! A wonderful week.

Mick, Heather & Katie – Gli Avi, September 2020

What a relief to get away during Covid-19 to the peace and tranquillity of La Madonnina. We have seen the unique antiquity of Cast. Fiorentino, Cortona, Arezzo and Lucignano and their fine museums and churches – all in their architectural splendour. We have sunbathed and swam, walked and read, wine tasted and learned to make pasta – it’s been wonderful. Maria and Rinaldo have been great, despite the absence of a common language with the aid of Google Translate and French, we got on famously. Dining in on Maria's excellent authentic home cooking was a great decision but for our last night we ate marvellous medallions of fillet at La Muzzicone. We’re sorry to leave.

Peter & Hilly – Gli Avi, September 2020

What an amazing time we had in Tuscany, made all the more special with our stay at La Madonnina. We had amazing support from Jonathan Magoni who made our travel around Tuscany so much easier by his many super recommendations.

Christine Cowley, September 2020

Getting away is no mean feat in a global pandemic, but this region felt very safe, uncrowded and a blissful escape. Day 2: Cycled into town for coffee, lunch and had dinner in Cortona. Day 3: Headed to Lake Trasimeno, Montepulciano, Pienza. Day 4: drove to Siena for the day – beautiful city with a cathedral. Did the tour but recommend booking ahead for the Gates of Heaven tour. Ate lunch in town at Silla’s, which is the best restaurant by far. Maria cooked supper. Day 5: Visited Chianti region. Day 6: Bike ride, coffee, lunch, pool time and ate at Silla’s – oh, and got engaged there!! Day 6: Back to Montepulciano for wander, coffee, lunch and shops. Pienza for lunch. Lovely town. Dinner in Cortona, which is lovely in the evening.

John & Christine – La Nonna, September 2020

Many thanks for an excellent stay. We had a perfect holiday and now feel fully recharged and hoping to visit again.

Martin & Amelia – Gli Avi, September 2020

We had a wonderful two weeks at La Madonnina. The property is charming, with amazing views and a beautiful garden and swimming pool, and Maria is a fantastic host who made us feel so welcome (with gifts of home grown vegetables and ice cream and bubbles for the kids). The location is perfect with picturesque hill towns within easy reach, and we also enjoyed trips to Florence and Siena. Jonathan at Simpson Travel was very helpful and responsive, recommending and organising restaurants and trips for us, which really helped to make it a memorable and relaxing trip.

Charlotte Hawkins, August 2020

A wonderful, relaxing escape from the madness of the pandemic. Thoroughly enjoyed evenings on the terrace watching the sun go down. Explored Arezzo, Cortona and the late. Thank you Maria for the delicious meals.

Victoria, Simon & Sacha, August 2020

Beautiful location and villa with wonderful hosts. Maria takes everything in her stride and really goes the extra mile for her guests. The location is spot on for day tripping and a peaceful retreat in the evenings. We absolutely loved it.

Greg & Wendy Pearce, October 2019

Stunning valley, beautiful house and absolutely wonderful hosts, Maria and Rinaldo. What can we say? Nothing is too much effort and their enthusiasm to showcase the surrounding Tuscany is infectious. Maria – thank you for your cooking, teaching us the art of pasta and your energy and warmth. Fabulous end to our first Italian adventure. We have seen a lot and learned a lot. Gli Avi was a very comfortable and cosy villa and we feel honoured to have experienced it (best bed so far!). The world ‘bellisimo’ comes to mind.

Greg & Wendy – Gli Avi, October 2019

It would be all too easy to stay put at La Madonnina and if you did you’d have a special holiday. We’ve enjoyed this tranquil place of natural beauty every morning and evening, enjoying Maria’s simple and delicious cuisine and a superb Tuscan Cucina dinner on our last night. However, to say put would mean you’d miss out on the spectacular Tuscany on the doorstep. Venture no more than an hour and you’ll discover so many places. We enjoyed Cortona, Arezzo and then by train to Florence (1hr 20mins) is easily accessible and a day’s outing through Tuscan towns is a must. We’ve driven nearly everywhere and haven’t been too stressed by this. Thank you to Maria and Rinaldo for a wonderful stay.

Catherine & Simon, September 2019

We had a lovely week and enjoyed visits to the many places in the area. We especially like Cortona. Maria and Rinaldo made us so welcome and Maria’s cooking is amazing. We had wine tasting nearby – all organic wines and homemade in clay pots as the Romans did! After a day in the car relaxing by the pool finishes the day. Thank you Maria for taking care of us and really enjoyed your company.

Nick & Malika, September 2019

Maria and Rinaldo, the owners, were extremely friendly and welcoming to their home. Breakfast on our terrace overlooking vineyards and olive groves was a delight every morning. In addition, we took advantage of the opportunity to have three dinners cooked by Maria, who is an excellent cook.

J Cash, September 2019

We have had such a very enjoyable week with Maria being very welcoming since the beginning. Our first meal made by Maria was an excellent introduction to Italian cuisine. We enjoyed a great day in Florence after travelling by train, visiting the famous Duomo and museum.

Helen, Chris, Jasmine, Amelia, August 2019

Wonderful week here. Well looked after by Maria and Rinaldo. Easy train into Florence. Don’t miss Maria’s amazing pasta dishes – the ravioli and Ragu are superb. Watching the shooting stars on the patio after a lovely dinner is a joy. We’ll miss Jack and especially Ava, rolling on her back getting her belly rubbed! (Two dogs, just for clarity).

The David family, August 2019

Beautiful, spacious, spotless and well equipped apartment hosted by the wonderful and very welcoming Maria. She was very accommodating of our two 6-year-olds who bombarded her with questions, and she kept bringing us ‘extras’ from home-made biscuits to freshly picked, cooked green beans. And her meals are delicious and such good value. All with local wine included. Ten minutes’ drive to the nearest town which has supermarkets stocked with all you need. Local pizza place a few hundred metres away. Lovely pool which our children couldn't get enough of. Just one other family staying at the same time as us gave it a really cosy feel. Perfect for a rural getaway.

Deepha Balasundaram, August 2019

La Madonnina is rustic, tranquil with exceptional hospitality. We enjoyed lazy days taking in the beautiful surroundings whilst eating breakfast and swimming in the pool. Maria is an exceptional cook and we had many evenings in sampling her amazing dinners. The spinach and ricotta ravioli with ragout is delicious. A most enjoyable and relaxing holiday was had by all three generations of our family.

R Buckner, August 2019

We’ve had such a lovely stay here in La Nonna and have been looked after so well by Maria. We have two young children so to be able to have the flexibility of our own kitchen to cook in, the balcony to relax and the pool have made this a very relaxing home to return to at the end of a busy day exploring. Our children have especially loved ‘visiting’ Maria who has been most obliging. She made lovely meals – probably the best we’ve had.

Simpson Traveller, July 2019

Maria was so warm and welcoming. She and Rinaldo treated us like family. We could not have enjoyed our holiday more!

Fiona Grassick, June 2019

I have fallen in love with Tuscany and it’s partly down to you, Maria, and your hospitality. You have a wonderful home and I can never get tired of looking at that view. You made us both feel very welcome and we loved the cooking lesson. Hope you have an endless supply of guests as your home deserves to be full. Many thanks for a fantastic holiday.

Graham & Monna, June 2019

First time in Italy with Simpson and first time in Tuscany – what a beautiful place and such friendly people everywhere. Visiting Florence from here is easy with direct trains. Maria and Rinaldo have been superb hosts – nothing is too much trouble and we have laughed every day with them. Best lasagne ever!

Mark, June 2019

What a wonderful week we’ve had. Maria and Rinaldo are perfect hosts, generous and so friendly. We will never tire of the views, a peaceful tranquil place to sit and completely relax.

Johnny & Rittie, June 2019

What a wonderful week we have had. Maria and Rinaldo are perfect hosts, generous and so friendly. We will never tire of the views, a peaceful tranquil place to sit and completely relax.

Johnny & Rittie, June 2019

I have fallen in love with Tuscany and it’s partly due to Maria’s hospitality. She has a beautiful home and I never tired of looking at that view. They made us both feel very welcome and we loved the cooking lesson. Hope they have an endless supply of guests as their home deserves to be full. Many thanks for a fantastic holiday.

Graham & Monna, June 2019

We’ve had a truly wonderful time in this most beautiful part of Italy. The hilltop towns are a joy to visit and explore. Maria and Rinaldo – you are such excellent hosts – so amenable and obliging – the trip to the local winery and olive oil processing plant was a bonus. Thank you for everything you did ‘as part of the Simpson empire’ to make our stay so enjoyable.

Howard & Louise, May 2019

Dear Maria and Rinaldo. We have had a restful week at your lovely cottage. It is a lovely valley and we enjoyed the walks along the river/canal to local villages. The breakfasts and swimming pool are great – many thanks for a great holiday.

Steve, Belinda & Jenny, May 2019

La Madonnina is a perfect venue for a relaxed time away. Maria and Rinaldo are excellent hosts and the style of their relationship with their guests is most welcoming and warm. The surroundings are picturesque and delightful and within reach of many of the best cultural sites in Italy.

Barry & Pat, September 2018

La Madonnina was a lovely, peaceful place to stay. Maria was an excellent, friendly host and couldn't do enough for us. It's a quiet location which is wonderful for relaxing, but Florence, Arezzo and Sienna are within easy reach. There are good restaurants in Cortona and Castiglion.

Mr Spence – La Capannina, August 2018

Four of us had a relaxing, hot and sunny week at La Madonnina. Gli Avi is a comfortable base with a welcoming and very friendly hostess (and characterful puppy, Eva). Breakfasts were open air and tasty and the two dinners that Maria cooked and served were excellent. The views from the terrace are magnificent and the pool inviting. The area is very attractive. Just perfect!

R Shaw, August 2018

La Madonnina is a perfectly lovely property which we would visit again and again.

Diane – La Capannina, August 2018

Maria has been a wonderful host at La Madonnina, and despite our limited Italian and Maria’s limited English, we managed to have lots of happy conversations together. Maria welcomed us into her home to watch England play in the World Cup and also prepared a delicious meal on our first evening. The local area is stunning and with lots of interesting places to visit – Cortona and Arezzo are both within easy reach.

Mike & Geraldine – Gli Avi, July 2018

What a wonderful place to relax and enjoy the amazing views. Maria cooked us two fabulous meals and we were joined by the others also staying there. Many thanks to Maria and Rinaldo for making our stay at La Madonnina so special.

Rowena, Martin & Gaby – Gli Avi, July 2018

We spent a lovely week at La Madonnina. Castiglion Fiorentino is a great town with really nice places to eat. If you don’t fancy going out, Maria cooks a fabulous meal and there is loads to eat. Maria is a wonderful host and nothing is too much trouble.

The Holder Family – Gli Avi, July 2018

We thoroughly enjoyed our stay at La Madonnina. Our host, Maria, was friendly, helpful and went out of her way to make us feel welcome. The breakfasts each morning were fresh and plentiful and our welcome evening meal was so delicious that we had another one on our last evening! All three accommodation options were beautifully presented and well appointed. We loved our holiday.

Mrs Hatton – La Capannina, July 2018

We book with Simpson Travel as we know what we will get – out of the ordinary in every way, great locations, fabulous hosts and kindred spirits. Both our selected properties in Tuscany, La Madonnina and La Canonica di Cortine, had so much to recommend them whilst being totally different – a great combination.

Martin Sims – Gli Avi, July 2018

Lovely region, lovely tours, fabulous property, really enjoyed conversing in broken Italian/English with Maria and Rinaldo. It’s a gem of a spot and we won’t forget it. Well done Maria. Well done Simpson Travel.

John, Skye & Kara– La Nona, July 2018

We had a great time at La Madonnina. Maria and Rinaldo could not have been more hospitable and we came away feeling that we had experienced a slice of authentic Italian life. If you get the chance to make pasta with Maria it really is an opportunity not to be missed – we thoroughly enjoyed it. I can also recommend sampling her home cooking – delicious. It’s in a central location from where you can explore the beautiful region of Tuscany. I can recommend taking the train to Arezzo and Florence, which we found very straightforward. There is much to do and see within easy reach and we particularly enjoyed Cortona which is only 20 minutes or so by car.

Mr & Mrs Fletcher – La Capannina, July 2018

We had a wonderful stay at La Madonnina and Maria was a fantastic host. The breakfast view will live with us forever. We really enjoyed visiting Cortona and our trip to the lake.

Janine & Martin – La Capannina, July 2018

We had an amazing time, thank you so much. Maria’s cooking was fabulous and was a real treat to sit on the terrace enjoying amazing food. We loved the area and enjoyed re-visiting many places that we have visited before.

Karen & Gary – La Nona, July 2018

We had the most wonderful time. One week at La Madonnina was not enough to explore such a beautiful location – the only option is to return! One of the highlights for us was learning to make pasta with Maria. We can’t recommend it enough. She is a superb cook and we enjoyed one of her meals on our last night. We were so sad to leave. We loved Cortona, Arezzo and Florence. Travelling by train was easy…. Thank you very much Maria and Rinaldo.

Vikki & John – La Capannina, June 2018

Tranquillity is what we look for on a holiday and La Madonnina provided this and more. It was wonderful to see the roses at their very best. We were two couples staying in La Nonna and we loved our little cottage, especially the cosy terrace. Our day trips included Cortona and Arezzo. Ask Maria for some of their olive oil and the neighbour’s red wine!

Rosie, Jozef, Jan & Aad, June 2018

One of our best holidays in Italy – the perfect setting, good weather and such a warm and generous welcome from Maria, who could not have been more helpful. We did not need to venture very far (though Cortona is delightful), and we spent most of our time painting and pottering locally. Maria and Rinaldo are such good hosts. We will miss La Madonnina.

Su & Jon – Gli Avi, June 2018

This has been a wonderful place to stay and experience the beauty of Tuscany. It has been made even more relaxing by the stunning surroundings, the delicious (squisito) food, local wine and Maria’s generosity. Cortona, Castiglion Fiorentino, Montepulciano, Florence and Arezzo have been beautiful places to visit and the wild flowers at this time have been wonderful. Thank you.

Mr and Mrs C, May 2018

This is my 3rd or 4th holiday with Simpson Travel and I cannot fault them. It is so nice to deal with a company that speaks to you regularly and sorts out any problems and is so knowledgeable about their properties. I run my own business and if my staff were half as friendly and attentive I would be very happy.

Mr Beese, May 2018

La Madonnina has been a wonderful place to stay and experience the beauty of Tuscany. It has been made even more relaxing by the stunning surroundings, the delicious food, the local wine and the generosity of Maria. Cortona, Castiglion Fiorentino, Montepulciano, Florence and Arezzo were beautiful places to visit and the wild flowers at this time were wonderful.

Lucy & Pete – Gli Avi, May 2018

We’ve had an amazing week at La Madonnina. Trips to Siena, Rome and Cortona, winemaking at the vineyard down the road and a lot of relaxing by the pool. Maria was incredibly helpful and hospitable and all these things combined made it a memorable time.

Mark Wright & Kay Steven – La Nonna, May 2018

What a wonderful place, so beautiful and peaceful. The apartment is lovely and the beds so comfortable. Maria has been so kind and the breakfasts have been amazing. She also brought us some treats in the evening! We drove to Cortona which was fascinating and took the train to Arezzo. Unfortunately we did not stay long enough to do a few more trips, but at least we had a very restful time. We will remember the stunning views.

Pat & Brian D'Olier – La Nonna, May 2018

Just like everyone else that has stayed here, we have had an amazing week! Maria and Rinaldo have looked after us so well. Maria’s cooking is amazing and we managed to get the rest we so desperately needed.

Penny & Mick – Gli Avi, May 2018

We’ve had a wonderful first family holiday here with our baby. Maria is a marvel – do sample her delicious cooking and see how she makes pasta. Remember to visit Cortona – we had a lovely lunch at Logetta (on the terrace overlooking the square). La Madonnina is obviously in a beautiful serving, but Maria’s hospitality and warmth made it extra special. We would love to come back.

Rebecca, Ross and Edward, September 2017

A delightful week at La Madonnina! Maria is the perfect hostess and made us feel instantly at home in our comfortable apartment. We greatly appreciated her cooking after a day's sightseeing in this beautiful part of Tuscany. The breakfasts on the terrace gave us the opportunity to meet our fellow guests and compare notes on our excursions.

The McClelland's, September 2017

Thank you so much for the welcome at La Madonnina! We have enjoyed a fantastic week here in Tuscany. Maria, Rinaldo and Jack have been amazing hosts and have made our stay so much better. It is a wonderful location to explore with Sienna and Florence so accessible by rail and car. This has been our first family holiday to Italy and we will definitely be back for more!

Colin, Alison, Cadi, Matthew & Nan, September 2017

Thank you Maria and Rinaldo for looking after us so well. We had a lovely time.

Roger and Jane, September 2017

Very much enjoyed staying at La Madonnina and thank you to Maria for her hospitality throughout. I can now make pasta like an Italian! So many lovely places but loved Arezzo and natural spring spa at Rapolano and the Chianti Run.

Andrew and Lorraine, September 2017

We have spent two very happy weeks at La Madonnina in the care of Maria and Rinaldo. We loved the area – sitting on our terrace looking at the views is such a splendid way to pass time! We have been to see lots of wonderful places including Siena, Montepulciano, Montalcino, Cortona, Arezzo, not forgetting our local special town of Castiglion Fiorentino. We have eaten and drunk well – the Tuscan food and wine is delicious. Oh some more time here!

Jan and Norman, September 2017

Thank you so much Maria for making our stay so welcoming. We had a lovely week with fantastic weather and enjoyed seeing Arezzo and Cortona.

The Crowns, September 2017

This is my third time in Italy and I loved it. Every night the view is amazing. I loved all the food and it was fun to play with Jack.

Issy, aged 9, August 2017

We had a wonderful time at La Madonnina. Beautiful place and scenery. Maria and Rinaldo are amazing hosts,couldn't do enough for us as a family.

Mrs Colbert, August 2017

What a wonderful place to stay! Maria and Rinaldo, you have been excellent hosts! Thank you so much! Siena really worth the drive and Cortona was one of the best towns we have visited in Italy! So gorgeous in the evening too. An absolute delight.

Lavina, Simon, Sam and Max, August 2017

Thank you very, very much for welcoming us at La Madonnina! We enjoyed the beautiful views, the pool and visiting the nearby villages. Maria is a wonderful host, always ready to help or play with the children. Thank you!

Stefan, Maria, Abel & Pierre, August 2017

We had a fabulous week at La Madonnina. Maria is a wonderful host and we enjoyed the lovely home-cooked meals on several occasions. La Nonna is extremely comfortable (especially the beds!) and the pool is delightful with fantastic views across the valley – not to mention lovely and cool as we have dodged the 40+ temperature this week. We enjoyed Assissi and Corbana particularly and the Tuscan countryside in general. Thank you Maria, Rinaldo and Jack for a lovely relaxing week.

Bronwen, Steve and Sam, August 2017

We had a brilliant stay here, thank you so much for all the places you recommended. Thank you for making this such an enjoyable stay (especially Maria). The site was peaceful however it was only a short drive to a number of restaurants and activities. Thank you.

The Wolstenholme family, August 2017

Thank you for a truly relaxing stay at La Madonnina. It has been a perfect setting to enjoy the wonderful breakfasts, lazy lunches and hours of fun in the pool. We loved our week here in Tuscany. Thank you Maria and Rinaldo for welcoming us into your home.

Simon, Lesley, Phoebe & Ted, August 2017

We had a lovely holiday at La Madonnina... The host was superb and the accommodation was a lovely rural Tuscan experience. Very peaceful and relaxing.

Audrey Riddle, July 2017

We have spent a wonderful two weeks here as a family of four – as we sit on the terrace on our last evening, having enjoyed yet another of Maria's fabulous home cooked meals. We are very sad to be leaving especially Maria, Rinaldo and Jack! This is such a special place and the hospitality offered by Maria is second to none – she treats you as family, welcoming you in her home and we have certainly felt adopted by her! La Madonnina is a great place in which to relax and retreat to after busy days spent exploring Tuscany. As other guests have suggested – the train is great – local, fairly priced, easy to use and free parking at the station, which makes it a good alternative to driving into the cities. In spite of the wide choice of restaurants, our favourite meals have certainly been cooked by Maria – truly wonderful! Thank you Maria and Rinaldo for a wonderful and holiday and making our first Italian family holiday so memorable.

Karen, Graham, Amelia & Olivia Potts, July 2017

Just wanted to confirm what you described as a fabulous holiday location – Maria at la Madoninna is just fabulous. We wanted to share our delight of what we've experienced so far – we only arrived last night!! Fabulous location, amazing hospitable hosts – perfecto!

The Potts Family, July 2017

Wonderful stay at La Madonnina. Maria was an amazing host. If you are lucky enough to have her home-cured prosciutto and salami you are in for a treat. Castiglion Fiorentino is a wonderful local town. We ate at Silla’s Bistro and Muzzicone – both very good especially the steak at Muzzicone. There is so much to see in Tuscany but don’t overlook Cortona and Arezzo (by train) as local trips.

Peter & Jo, July 2017

Maria at La Madonnina was really lovely. Very helpful and friendly.

Barbara Sedgwick, July 2017

We enjoyed our stay very much and the owner of the property (Maria) was extremely helpful and could not do enough to ensure our comfort. I have no criticism whatsoever and would not hesitate to go back.

Donald Heath, June 2017

We've had a wonderful stay here. Maria has been a fabulous host. Breakfast has been delicious and Maria was flexible on times when we wanted an early start to catch the train to Florence. We visited Cortona and Lake Trasimeno, both easily reachable by car. Siena is just over an hour by car and is a fabulous city to visit and explore. This is our last evening in this very tranquil and relaxing place. Maria fetched us pizza to eat on our balcony – perfect with a bottle of local red wine! Thanks for an excellent holiday.

Dave & Linda Hendrey, June 2017

We've had a brilliant time here at La Madonnina. Beautiful place and wonderful hosts. Nothing is too much for Maria – a truly lovely person!

John and Sara Coghler, May 2017

Our choice of Italian properties is diverse, ranging from simple charm to genuine luxury and style. Much of our portfolio is privately owned, and price alone is therefore not a universal guide. We contract all our accommodation in person, and each property has its individual appeal.

To help you make the right choice based on your own priorities, we have devised a simple grading guide to be considered in conjunction with each individual property description, awarding up to a maximum of five stars for the below categories.


Property Grading Key:

  • 5/5


  • 4/5

    Very good

  • 3/5


  • Location


    Position, view, serenity, privacy

  • Comfort


    Space, style, overall furnishings

  • Facilities*


    Property enhancements

  • Amenities*


    Proximity to beaches, restaurants and shops

* For further clarification on Facilities and Amenities, please view the 'Details' tab for each property or speak to one of our experienced sales consultants.

From the moment you arrive in Tuscany, you are invited to share in its grand passions and indulgent pleasures – world-famous wine, mouth-watering food and epic histories. Each of Tuscany’s ten provinces has its own unique personality, but wherever you stay, you’ll find yourself surrounded by a verdant patchwork of olive groves, cypress trees and vineyards. From the birthplace of the Renaissance, Florence, to the narrow streets of hilltop San Gimignano, Tuscany makes for a stunning escape. 

To complete the picture, explore our collection of handpicked villas and charming apartments.

Explore our pre-bookable experiences in Tuscany



Read more on our Tuscany region page

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