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Charming Chianti hilltop house, exceptional views, large swimming pool

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Living room
Master bedroom
Second double bedroom
Dining room
View of Living Room into Sitting Area

Reviews

10 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Parking available
  • Laundry
  • Kitchen
$304
avg per night

Explore the area

View in a map
Siena, Tuscany
  • Place, Casina di Cornia Winery
    ‪15 min walk‬
  • Place, Mazzei Winery
    ‪25 min drive‬
  • Place, Piazza del Campo
    ‪46 min drive‬
  • Airport, Florence (FLR-Peretola)
    ‪76 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

1 bathroom

Bathroom

Bathroom

Shower only

Bathroom

Shower only

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area
Price is $304 avg per night

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About the neighborhood

Castellina in Chianti

Located in Castellina in Chianti, this farm stay is in a rural area. The area's natural beauty can be seen at Chianti Sculpture Park and Alta Val d'Elsa River Park, while Museo del Cristallo di Colle di Val d'Elsa and Museum of Torture are cultural highlights. Chianti Observatory and Borgo di Vescine - Tenute di Castelvecchi are also worth visiting. Discover the area's water adventures with swimming nearby, or enjoy the great outdoors with cycling.
View more Agritourism in Castellina in ChiantiOpens in a new window

What's nearby

  • Casina di Cornia Winery - 15 min walk - 1.3 km
  • Mazzei Winery - 25 min drive - 12.9 km
  • Fortezza Medicea - 44 min drive - 29.4 km
  • Piazza del Campo - 46 min drive - 30.8 km
  • Siena Cathedral - 46 min drive - 34.8 km

Getting around

  • Monteriggioni Badesse Station - 14 min drive
  • Florence Airport, Peretola (FLR) - 62 min drive

Restaurants

  • ‪Riserva di Fizzano Hotel Castellina in Chianti - ‬24 min drive
  • ‪Dievole Wine Resort - ‬26 min drive
  • ‪Osteria Il Re Gallo - ‬15 min drive
  • ‪Albergo Casafrassi - ‬16 min drive
  • ‪Antico Travaglio - ‬25 min drive

About this property

Charming Chianti hilltop house, exceptional views, large swimming pool

Farmhouse in Siena area, Tuscany, Italy: Well equipped property of 157 M2 forming part of a renovated historic farm hamlet. La Casetta is beautifully restored in traditional style with exposed beams, old terracotta floors, and modern marble bathrooms. It is conveniently arranged over the entire ground floor of a large farmhouse divided into two separate and completely private units. It has its own entrance with private terrace and gardens. There are comfortable arched living and dining rooms and the entire property is equipped with a combination of antique and modern Italian furniture. La Casetta is well-stocked with books, music and videos, and an open log fireplace. There are 2 double and 1 twin bedrooms, and a fully equipped kitchen.
Pools and a tennis court are on the estate.
Our prices include all fees. No hidden fees.

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
default

Smoking

Smoking allowed: in designated areas
Outside please

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector and a smoke detector
Property Registration Number IT052005C2MQLRPYKF

We should mention

All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed GBP 5000, due to national regulations; for further details, please contact the property using information in the booking confirmation
A car is required for transportation to and from this property

Frequently asked questions

Does Charming Chianti hilltop house, exceptional views, large swimming pool have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Charming Chianti hilltop house, exceptional views, large swimming pool?

As of Mar 30, 2026, prices found for a 1-night stay for 2 adults at Charming Chianti hilltop house, exceptional views, large swimming pool on May 2, 2026 start from $304, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Charming Chianti hilltop house, exceptional views, large swimming pool pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Charming Chianti hilltop house, exceptional views, large swimming pool?

Check-in begins at 3:00 PM.

What time is check-out at Charming Chianti hilltop house, exceptional views, large swimming pool?

Check-out is at 10:00 AM.

Where is Charming Chianti hilltop house, exceptional views, large swimming pool located?

Situated in a rural location, this farm stay is 1.5 mi (2.4 km) from Mazzei Winery and 2.5 mi (4 km) from Lilliano Estate Winery. City Hall Castellina In Chianti and Castellina Fortress are also within 6 mi (10 km).

Charming Chianti hilltop house, exceptional views, large swimming pool Reviews

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 23 reviews
Rating 8 - Good. 2 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

9.8/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jocelyn H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Tuscan Villa

We had a wonderful stay at the villa which enjoys stunning views over the countryside. It is clean and spacious, with a great kitchen and 3 modern bathrooms. The pool was very popular given the high temperatures the week we stayed. Highly recommend organising for Serena to come and cook dinner, it was a highlight of our stay!
Stayed 6 nights in Jul 2023
Verified

10/10 Excellent

Ron M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Heaven on Earth

The property and grounds are well taken care of. The house was clean and had everything that we needed. The views of the landscape from the villa are spectacular. The sunsets were breathtaking. The best way to describe this place that is so beautiful and peaceful …. is heaven on earth.
Stayed 6 nights in Sep 2023
Verified

10/10 Excellent

Werner S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful holiday

The apartment is marvellous and very good equipped. Every bed room has its own bathroom. The view is a dream, you can see miles over wine yards. The pool is large and used by just a few guests. The whole area is quite.
Stayed 6 nights in May 2023
Verified

10/10 Excellent

Zuleikha N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Le Bagnaie

The house is beautiful, tastefully decorated and very complete, and comfortable for both sunny and rainy days. The lovely garden has several little sitting areas as well as a place with BBQ and table to have dinner. Everywhere you are the view is just stunning. The beautiful swimming pool is very big so it never feels crowded, also with breathtaking views wherever you look. The estate is situated in the heart of Toscana, perfect to discover al the beautiful cities and countryside. Site manager/customer liaison Jacky was very friendly and has all the information about the house and area you might need. Emailing with house owner Anne was also very pleasant. Both were very kind and swift to answer all the questions you might have. We had a wonderful stay and will definitely return! fam. de Vos, The Netherlands
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Gail C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best VRBO Experience Ever!!!

Ann and Richards rental was the highlight of our 21 day vacation which included a 12 night cruise, Greece, Turkey, Amalfi, Rome and Florence, so that’s saying a lot. We felt like we had walked onto a movie set. We hit good weather so the views of the hills and vineyards was breathtaking! The terrace was enchanting, and the apartment itself was a combination of old world charm with a modern eye for detail. Large bedrooms, comfortable beds, well stocked kitchen complete with colorful and cheerful ceramics. Serena, the gardener’s mother prepared a delicious Tuscan meal for us at a very reasonable price. Jacky, the mgr was attentive to emails and quick to respond. Ann-and Richard have a slice of paradise, and if you have the opportunity to book this place, do not hesitate. We could not stop taking photos, so if you love photography….
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Clémentine G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Merveilleuse semaine dans cette vieille demeure très bien équipée, où l'on se sent comme chez soi. Les vues sur la Toscane sont à couper le souffle, la piscine est superbe et très grande, les jardins et le tennis parfaitement entretenus. Beaucoup de réactivité de la part de notre hôtesse et de sa représentante sur place pour répondre à nos questions. Un endroit magnifique et chaleureux où l'on espère revenir.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Françoise C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Un site exceptionnel !

Emplacement exceptionnel dans une demeure typique de la Toscane et pleine ce charme. L’appartement est décoré avec beaucoup de goût. Il est très spacieux et situé dans un écrin de verdure , sur un promontoire qui domine la campagne alentour et les villages de San Giminiano et La petite ville de Sienne. Très au calme au milieu des chants des oiseaux! Les jardins sont entretenus de façon remarquable. Le petit feu dans la cheminée le soir est un plus très appréciable ! Enfin le chianti qui nous attendait pour l’accueil était vraiment bienvenue et appréciable ! Merci aux propriétaires pour un tel accueil !
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

Jens J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Grosszügige Wohnung

Grosszügige, bestens eingerichtete Wohnung mit schönem Garten - meine ganze Familie fühlte sich sehr wohl.
Stayed 12 nights in Apr 2022
Verified

10/10 Excellent

Helena G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Un sogno diventato realtà

Con la famiglia relax e divertimento in piscina e sul campo da tennis nel giusto equilibrio , cena a lume di candela con il bbq a disposizione con vista su San Gimignano al tramonto . Cipressi , ulivi e vigneti come contorno . Semplicemente un oaradiso . Consigliato a chi sa rispettare il prossimo.Tutto rispecchia le caratteristiche descritte , casa di Anne fantastica e l’accoglienza e assistenza di Jackie impeccabile .
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Martin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Traumhafter Toskana-Urlaub

In einer malerischen Ansammlung von Rustico-Häusern gelegen, besticht dieses sehr gut ausgestattete und ansprechend eingerichtete Ferienhaus zusätzlich durch den panoramaartigen Postkartenblick über weite Teile des Chianti-Gebietes. Die Vermieter und der Service vor Ort sind über aus freundlich und zuvorkommend. Kurzum: ein Toskana Urlaub wie es schöner nicht sein könnte! Dieses Ferienhaus weckt den Wunsch, so schnell wie möglich wieder zu kommen und ist absolut empfehlenswert.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Francesco D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and relaxing journey

The house was really comfortable and the location impressive. The efficient and cozy assistance of the landlord and co. during all the journey was constant and helpful. Looking forward to coming back next year!
Stayed 7 nights in Aug 2020
Verified

8/10 Good

gerard m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Superbe

Propriété magnifique avec une vue imprenable, un hameau entretenu à la perfection, une piscine XXL. maison des plus agréables avec tout le confort nécessaire. on se serait cru comme à la maison, rien ne manquait. la région est superbe. Ce fut très agréable de revenir dans cette région et j'espère y revenir à nouveau.
Stayed 7 nights in Aug 2020
Verified

10/10 Excellent

Theron T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay in Tuscany

This is a beautiful property that has all the amenities that families, couples and food & wine lovers could possibly need. We've stayed here 3 times for a total of 6 weeks and will go back again if we get the chance.
Stayed 14 nights in Dec 2019
Verified

10/10 Excellent

Bettina P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wunderbare Ferien

Gute Ausstattung, schöner Blick und herrlicher Pool!
Stayed 13 nights in Jul 2019
Archival

10/10 Excellent

caroline c.

Beautiful Tuscan hilltop

We have repeatedly stayed at La Cassetta with our three girls and it never disappoints. Beautiful views from the garden where, in the evenings, you can watch the sun setting over the Tuscan hills. The accommodation is well maintained and equipped and the children love the pool which must be one of the biggest in Chianti! Le Bagnaie is the perfect location for exploring local towns, the nearest being the picturesque Castellina in Chianti. There are also plenty of great restaurants, hidden away in the local country roads, to be explored. All very family friendly and relaxed.
Archival

10/10 Excellent

Elizabeth K.

A fantastic stay in the middle of Tuscany

This is a fabulous villa. We have stayed there several times, and it is my favorite destination. The villa is truly a place that can make you feel at home in just a couple of days. There are three patios for sitting outside and enjoying the Tuscan sun and countryside. Of special note is all the help you can receive if needed. The manager Jackie (who speaks English) is just a call away to answer any questions. And there is a cook Serena who will come and prepare a fantastic meal, serve you, and do all the clean up. What could be better? Of course, the location is perfect, right in the middle of all the cities and things to visit. This is just a perfect spot from which to experience Italy, sit out on the patio, sip great wines while eating meats and cheeses, and watching the sun set. My husband and I live in Florida, and we always look forward to coming back.
Archival

10/10 Excellent

Emmanuelle B.

une maison rêvée, un bijou en Toscane

Cette maison est rêvée pour des vacances en famille. Maison calme, spacieuse, confortable, chaleureuse. La piscine est immense, le tennis est toujours libre. Nous avons accès à un potager et des arbres fruitiers. Le personnel, sur place est serviable, dévoué avec un ménage régulier. La situation est idéale, pour visiter Sienne (à 15 minutes) Florence (à 30 minutes)Lucca, Pise, San Gimignano... Le prix est léger en regard du confort luxueux de cette maison. Le panorama sur les vignes du chianti est splendide. Je la conseille à tous.
Archival

10/10 Excellent

Amanda R.

Tuscany's best kept secret!

We have just returned from a wonderful week in Tuscany staying at La Casetta. We had high expectations of the accommodation before we arrived given the photographs, reviews and the description of the house not to mention the information that Anne provided prior to our arrival but that still did not prepare us for the beautiful location of the house with panoramic views of the Tuscan landscape. The house was very well equipped and comfortable for 6 adults and 1 baby and was absolutely sparkling clean and tidy. The gardens were well maintained and just a lovely peaceful place to have breakfast or to sit with a cold drink and admire the views. My husband and I have visited Italy many times but I have to say that we were overwhelmed by the beauty, scents and sounds that attacked our senses while staying at La Casetta. The facilities (the pool, boules area and tennis court) are well maintained. Nearby Castellina in Chianti provides good facilities, a co-op supermarket, grocer, bank, pharmacy, restaurants and various other small shops to entice and delight visitors. The local restaurants in nearby villages such as Lornano and Reserva di Fizzano are worth trying as they are of a very high standard and serve dishes using local produce. There are many places to visit within a 30-40 minute drive including Siena, San Gimignano and the much smaller Greve, Radda, Gaiole, not to mention the local vineyards that surround the property. I very rarely wish to return to the same holiday location as I have so many places that I would like to visit but I would definitely make an exception here as I loved it so much that I didn't want to leave!
Archival

10/10 Excellent

Tuscan Retreat

My wife and I have just returned from our 7th visit to this perfect haven in Tuscany. We have been every year since 2005 at various times of the year and the biggest problem we always have is coming home and deciding when we should go next! We lead fairly busy lives and La Casetta is the perfect location to escape to especially if you feel the need to recharge the batteries. We normally fly to Pisa, but on this occasion we flew to Rome, spent some time there and then made our way up to Tuscany. Both car journies are very straight forward with the trip from Rome only taking between 2 to 3 hours. If you enjoying walking there are several walks that you can choose from. Our favourite is the uphill climb to Fonterutoli, stopping for a drink and a bite to eat at the restaurant and then the stroll back down - around 5 to 6 miles in total. If you have never been to Tuscany I think you will be hard pushed to find somewhere better to rent and I would never hesitate to recommend it.
Archival

10/10 Excellent

Perfection

My family (wife & two young children) has stayed at this property for 6 consecutive years, always during the Easter school holidays. We fly to Pisa (BA / Easyjet / Ryanair) and hire a car for the 1hr 40min drive. We absolutely love the place. The location is unbeatable - on top of a hill with stunning views over picture postcard rolling countryside. It is within very easy striking distance of all the major attractions - (Siena, Florence, San Gimignano etc.) and the nearest town, Castellina-in-Chianti, is a regular draw whether for coffees, ice-cream, restaurants or the butcher. The property is one of eight that have been developed very thoughtfully from a farming hamlet. Although all the properties have their own gardens and enjoy great privacy, the grounds are managed as a single estate and this gives a great sense of "completeness". We are always impressed by the constant upkeep of the grounds and the (shared) tennis court and pool are first rate. The property itself is spacious and well laid out, yet very homely. Everything is clean and well maintained. The decor and fixtures and fittings are of a high quality, with all the esssentials - dishwasher, washing machine, BBQ, asparagus steamer (!) etc. The private terrace and gardens soak up an unrivalled vista. However, It is clearly much more than just a rental property. It has very much a family feel to it and the owner has always been tremendously friendly and helpful. For the last two years some family friends (also with two young children) have rented one of the adjacent properties. This place is a regular fixture in our calendar and is highly recommended.
Archival

10/10 Excellent

Jeffrey B.

Tuscan Treasure

We just returned from a week at this property. Although the home has room for six people we were only four. This home is VERY well loved by the owners and has all of the comforts that one could desire. From the first day that we contacted the owners we were treated with respect and honest discourse in all manners of the rental process.We will be back in the future when ever we visit this area. Wonderful home !!!!
Archival

10/10 Excellent

A Tuscan idyll

We have just returned from our second visit to this house in eight months and were delighted to be back in this wonderful place. The house is far more than a holiday rental; it is a family home, furnished beautifully with a mixture of modern classics and simple antiques. The kitchen has everything you could possibly need to cook a delicious Tuscan feast and the house is surrounded by vineyards. What more could one want? The estate itself is wonderfully maintained and sitting outside on one of the glorious terraces, surrounded by flowers, is unbeatable, especially when you catch a glimpse of San Gimignano shimmering in the distance! There are many wonderful towns and villages nearby with restaurants ranging from the simplest pizzeria to the most luxurious "grown-up" cuisine. The owner kindly provides a really useful lists of restaurants, both local and further afield, several of which we have been delighted to sample. This is the prettiest part of Tuscany by far and La Casetta is our best rental experience in the nearly 25 years we've been taking this type of holiday.
Archival

8/10 Good

Claire T.

July-Aug '09

We have a wonderful 2 week stay at this property. Thoroughly enjoyed the peace and tranquility and getting away from it all. A car is essential if your planning on staying - we flew in 2 yrs ago and hired a car, but this year we drove down to Tuscany from Leeds, England. A very good journey and even enjoyable. Property is well maintained and fully equipped. Take plenty of mosquito products if going in the summer months. Overrall - would highly recommend.