Villas in Province of Siena: Rent luxury villas in Province of Siena

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1 / 21

Villa Bacco with Pool (Max 16+4 ppl) - Valiano villa sleeps 20

Montepulciano / Valiano

8 20 7 nights min stay

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
Villa located on top of a hill and dipped between wineyards.Due to its strategic position, in Valiano di Montepulciano, half way from Rome to Florence and on the border between Tuscany and Umbria region, it will be easy to visit the most artistic towns in the heart of I  …see more

from £616 / night

£3880 / week

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from £616 / night

(13) Excellent 

1 / 24

Charming 2 bedroom Tuscan villa with private pool

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spend  …see more

from £173 / night

£475 - £1552 / week

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from £173 / night

1 / 20

house and wonderful garden of exclusive use

Sovicille / Torri

1 4 4 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
“Il Molino" was restructured in 2011 applying great care of the particulars; entirely surrounded with a wide wonderful garden, the complex lies in a very quite and immaculate wood between the Chianti hills. It is only 25 minutes by car or by train far from the ce  …see more

from £78 / night

£432 / week

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from £78 / night

Featured properties

(16) Excellent 

1 / 24

Attractive stone-built villa in extraordinary Tuscan locale, private terrace and swimming pool, incredible views, sleeps up to 9

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Villa La Porticciola take its charm from the extroardinary position in front of the silhouette of San Gimignano towers. Everywhere it is possible to admire the unforgettable panoramic view of the town or the hilly landscape of the Chianti region. Ideal position for excu  …see more

from £345 / night

£1466 - £2500 / week

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from £345 / night

1 / 14

villa in the heart of Tuscany - Montisi villa sleeps 14

Province of Siena / Montisi

6 14 4 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min stay
Key info: Child friendly ; Ask about pets; Private garden;
Poggio is a typical Tuscan villa of the 17th century, built entirely of stone, situated 3 km from the medieval village of Montisi and plunged the unmistakable landscape of the Crete Senesi. Its dominating position overlooks the area from Montalcino, Trequanda until Sien  …see more

from £475 / night

£1725 - £2500 / week

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from £475 / night

1 / 10

Villa il Poggio: Picturesque Tuscan holiday rental with pool access and stunning grounds

Province of Siena / Sinalunga

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; No pets allowed;
The apartment of Villa il Poggio Geranium is ideal for guests who want to spend relaxing moments in harmony and intimacy.This apartment set up all the necessary services to enjoy a stay full.If the instructions were not sufficient to have a complete picture of what you&  …see more

from £86 / night

£689 - £949 / week

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from £86 / night

(1) Excellent 

1 / 14

Villa Verdepino - Rigomagno villa sleeps 10

Sinalunga / Rigomagno

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The villa sits on a hill immersed in the greenery of a peaceful oasis and surrounded by large grounds.Here, where pleasure and nature meet, it is possible to enjoy long walks through the countryside and at the same time be within easy reach of amenities which are just 5  …see more

from £193 / night

£1345 - £9190 / week

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from £193 / night

1 / 43

Province of Siena / Vivo d'Orcia

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Ski; Child friendly ; Ask about pets;
 …see more

from £61 / night

£423 / week

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from £61 / night

(2) Very Good 

1 / 24

Province of Siena / Castellina In Chianti

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Nearest beach 85 km; Swimming pool; Child friendly ;
 …see more

from £198 / night

£1382 / week

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from £198 / night

(13) Excellent 

1 / 24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
The completely renovated property occupies a panoramic position within an estate of olive groves and vineyards, boasting an entrancing view of the famous towers of San Gimignano 4 km away. The characteristic architecture enables guests to experience a specifically Tusc  …see more

from £345 / night

£1552 - £2759 / week

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from £345 / night

1 / 32

Leccetino - Trequanda villa sleeps 6

Province of Siena / Trequanda

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Car essential;
Villa Leccetino Tuscany Arriving at Leccetino, down a short tree covered road is like arriving at a very secret location. Tucked into the hillside surrounded by olive trees, this is a spectacular masonry villa, made with stones dug up from the ground on this terraced p  …see more

from £278 / night

£1940 - £3440 / week

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from £278 / night

1 / 43

Villa La Casella - Cetona villa sleeps 4

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Treat yourself to the ideal 2-bedroom home for your dream vacation in Tuscany! La Casella is a luxurious private villa set on a gentle hillside with lush gardens and private pool, outside dining, views and close enough to walk into town. This well furnished villa is set  …see more

from £169 / night

£1177 - £2682 / week

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from £169 / night

(1) Excellent 

1 / 24

Casa Giovanni - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 7 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Italian village rental - This charming historic residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre.With origins dating back to the 15th century this property ce  …see more

from £240 / night

£1680 - £2360 / week

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from £240 / night

1 / 22

Province of Siena / Sovicille

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £130 / night

£863 / week

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from £130 / night

1 / 20

Casa Eleonora - Gallina villa sleeps 12

Castiglione D'Orcia / Gallina

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Just South of Siena, The Val d'Orcia is UNESCO World Heritage. Its enchanting towns and villages like Montalcino and Pienza are surrounded by a sea of vines and olives whose slopes intermittently give way to deep forest of pines, chestnuts and oaks, cool and refreshing.  …see more

from £186 / night

£1294 - £2113 / week

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from £186 / night

1 / 12

Villetta Bruco - Asciano villa sleeps 6

Province of Siena / Asciano

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 90 km; Swimming pool;
This large, 124 square metre, two-floor independent small villa has been created by connecting the old priest's accommodation with the coach-house.The ground floor is subdivided by an arch in the living room with fireplace and kitchen/dining room. On the ground flo  …see more

from £207 / night

£1466 - £1897 / week

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from £207 / night

1 / 15

Lovely 3 bedroom villa in the scenic Tuscan countryside wih large private garden and swimming pool

Province of Siena / Montisi

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Villa Montisi has been restored over the last few years with all the modern facilities within a traditional tuscan villa this makes for a truly unique holiday experience.Located in the scenic Val d'Orcia region which was declared a world heritage site by UNESCO.Thr  …see more

from £148 / night

£1035 - £1936 / week

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from £148 / night

(6) Very Good 

1 / 29

Province of Siena / Castelnuovo Berardenga

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £664 / night

£4647 / week

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from £664 / night

(1) Excellent 

1 / 19

Podere Tina - San Casciano dei Bagni villa sleeps 15

Province of Siena / San Casciano dei Bagni

7 15 1 night min stay

  • 7 bedrooms
  • Sleeps 15
  • 1 night min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
La Tina is located on a hilltop in the extreme north of the province of Lazio, bordering on Tuscany and close to Umbria. The hilltop where the former farmhouse, the stables and the swimming pool are located offers a glorious panoramic view of the undulating historical l  …see more

from £621 / night

£4397 / week

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from £621 / night

1 / 13

Traditional stone-built villa in Tuscan province of Siena with swimming pool, terrace and barbecue

Province of Siena / Montisi

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Three bed stone built home with all the traditional and style of an old tuscan home yet all the modern comforts.Air Conditioning is a must in Tuscany.This property has air conditioning in all rooms and is remotly controlled in each room.Two large bathrooms one with a ba  …see more

from £123 / night

£858 - £1548 / week

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from £123 / night

1 / 33

Country House Maramai in the lush Chiana valley

Montepulciano / Gracciano

5 9 7 nights min stay

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Maramai lies on the Gracciano estate, one of the most renowned producers of the Vino Nobile di Montepulciano, one hour south of Florence in the lush Chiana valley. The restored farmhouse with pool with 7 to 9 beds is the perfect base to explore the surrounding Tuscany l  …see more

from £292 / night

£2044 - £4069 / week

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from £292 / night

1 / 21

Villa Arpicella - Pienza villa sleeps 4

Province of Siena / Pienza

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 95 km; Child friendly ; Car advised;
Villa Arpicella really does offer the best of both worlds! Despite its prime location at just 10 minutes’ walking distance from Pienza, it enjoys the peace and quiet of a beautiful countryside setting with spectacular panoramic views. It is a large, traditionally Tusc  …see more

from £85 / night

£595 - £884 / week

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from £85 / night

1 / 24

I5.167 - Villa with pool i... - Vagliagli villa sleeps 6

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Child friendly ;
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly closed and the swimming pool, just below the house ground, has a lovely view over the valley and th  …see more

from £184 / night

£1283 - £2070 / week

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from £184 / night

1 / 18

The Artist's Villa (v042) - Gracciano villa sleeps 9

Montepulciano / Gracciano

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
This unique villa has, on the ground floor, a large entrance hall, a large living room with kitchen, dining room and central fireplace, a double bedroom, a bedroom with french bed (which could sleep 2 people), a bathroom with a shower, a bathroom with bathtub. On the fi  …see more

from £209 / night

£1457 - £2380 / week

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from £209 / night

1 / 29

Montepulciano / Abbadia di Montepulciano

5 10 1 night min stay

  • 5 bedrooms
  • Sleeps 10
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £739 / night

£5173 / week

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from £739 / night

1 / 29

Province of Siena / Montepulciano

5 9 1 night min stay

  • 5 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Swimming pool; Not suitable for children; Car advised;
 …see more

from £863 / night

£6035 / week

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from £863 / night

(1) Excellent 

1 / 25

Villa Corsano, SIENA - Ville di Corsano villa sleeps 20

Province of Siena / Ville di Corsano

10 20 6 nights min stay

  • 10 bedrooms
  • Sleeps 20
  • 6 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Typical Tuscan villa, ancient and charming. Large Dining room with huge fireplace (15 century). Frescoed ballroom. Some of the bedrooms are frescoed too. Extensive gardens with table to have dinners outside. Panoramic pool area overlooking Siena, the Crete Senesi and th  …see more

from £776 / night

£5432 / week

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from £776 / night

1 / 29

Tuscan Feeling - Casa Ornella - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Child friendly ; No pets allowed;
Located in the hills of the Val d'Elsa area, San Gimignano is famous mainly for its numerous noble towers that make this town, at the ancient atmosphere, one of the most striking and characteristic of Tuscany. A place where time has stopped, that has kept intact th  …see more

from £94 / night

£604 / week

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from £94 / night

1 / 11

Torrita di Siena / Montefollonico

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £52 / night

£363 / week

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from £52 / night

(1) Very Good 

1 / 27

San Donato - San Gusme villa sleeps 4

Castelnuovo Berardenga / San Gusme

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 115 km; Swimming pool; Not suitable for children;
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity. Part of the original estate of Villa Arceno, San Donato has a history that goes back many 100's of years  …see more

from £184 / night

£1285 - £1716 / week

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from £184 / night

1 / 9

Province of Siena / Sarteano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £95 / night

£518 / week

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from £95 / night

1 / 100

Valpoliziana - Montepulciano villa sleeps 8

Province of Siena / Montepulciano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 50 km; Swimming pool; Child friendly ;
Exteriorthe Villa boasts an absolutely perfect position, surrounded by rolling hills covered in vineyards and olive groves as far as the eye can see- the owners of the property in fact produce their own excellent wine and olive oil. Wonderful views from the villa also e  …see more

from £475 / night

£2156 - £3750 / week

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from £475 / night

(1) Excellent 

1 / 13

Your Villa in Tuscany with private garden and pool

Province of Siena / Sovicille

3 4 3 nights min stay

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 68 km; Swimming pool; Not suitable for children;
The holiday home "Il Rifugio del Falconiere" offers an elegant villa of 220 square meters with a large living room, where there is a fireplace and a unique décor, a large dining room, a fully equipped kitchen with dishwasher, refrigerator that produces ice and water, a  …see more

from £432 / night

£2587 - £3018 / week

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from £432 / night

1 / 13

VILLA STOMENNANO - Monteriggioni villa sleeps 6

Province of Siena / Monteriggioni

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Not suitable for children;
Borgo Stomennano will appeal to those who want not just a holiday villa , but who would like to sheer 17th century style and traditional Italian elegance. Written documentation of Stomennano date back to 1254 when in this place was sign the  …see more

from £794 / night

£5518 / week

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from £794 / night

1 / 10

Province of Siena / Siena

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
 …see more

from £493 / night

£3449 / week

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from £493 / night

1 / 20

San Gimignano / Ulignano

4 9 7 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Nearest beach 90 km; Swimming pool; Suitable for children age 5+;
 …see more

from £364 / night

£2544 / week

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from £364 / night

1 / 24

Trequanda SI - ITS920 - San Giovanni d'Asso villa sleeps 6

Province of Siena / San Giovanni d'Asso

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Child friendly ; No pets allowed;
Lovely holiday home in Trequanda, Siena - 3 double beds make up this villa complete with 2 bathrooms making it the perfect abode for a large family of 6 people. A microwave is one of the utilities provided at the holiday home. For guests relaxation there are mod con  …see more

from £74 / night

£517 - £664 / week

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from £74 / night

1 / 24

47263-Holiday house Siena - Pievescola villa sleeps 4

Province of Siena / Pievescola

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
This interesting one bedroom house is peacefully located at the edge of an ancient small hamlet overlooking the Elsa valley near Colle di Val d'Elsa. Ideal spot for couples and small families looking for a relaxing & cultural holiday in the heart of Tuscany.<  …see more

from £70 / night

£485 - £605 / week

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from £70 / night

(1) Excellent 

1 / 24

Villa Paradiso - Radda in Chianti villa sleeps 14

Province of Siena / Radda in Chianti

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The house has been lovingly restored and furnished with careful attention and eye for detail.The lovely gardens, which are to the rear of the property have an array of aromatic plants such as lavender with shady corners and a magnificent pergola for dining outdoors. Pri  …see more

from £241 / night

£1682 - £3250 / week

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from £241 / night

1 / 20

Primrose Villa (V039) - Chiusi villa sleeps 8

Province of Siena / Chiusi

3 8 7 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Child friendly ;
At Chiusi lake, this beautiful villa is a peaceful and cosy place for a holiday in close contact with nature. The restoration work, using environmentally friendly techniques paid attention to every detail, making the interiors light and comfortable. Extremely well furni  …see more

from £146 / night

£1018 - £2578 / week

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from £146 / night

Top Destination reviews

Casa Degli Olivi Cetona , Siena Tuscany
Italian friendliness, food, wine and culture at its best - Cetona - Tuscany

What a fantastic experience in the Italian countryside. Two weeks tucked away from tourist mayhem. Even prior to our departure from the Middle East to start our holiday, the owners answered all our enquiries quickly,efficiently with sound advice. The … see more
Tuscan apartment with pool in Cetona
Excellent, centrally located apartment in a charming village

We thoroughly enjoyed our stay in Cetona and, given half a chance, would go back tomorrow! We booked the apartment for two weeks with my husband and I spending the first week on our own, and our two sons and one girlfriend joined us for the second w … see more
Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more
I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
Perfect.

The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a S … see more
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … see more
Podere Val delle Corti
Very nice and total clean appartment

Beautiful property within a lovely environment Very nice and total clean appartment Landlady and the whole proprietor familiy are very friendly an helpful No kind of weakness has been discovered, at all … see more

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