Province of Siena apartment or villa with a heated pool | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
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  • Asciano (5)
  • Buonconvento (1)
  • Casole d'Elsa (1)
  • Castellina In Chianti (3)
  • Castelnuovo Berardenga (3)
  • Cetona (1)
  • Chianciano Terme (3)
  • Gaiole in Chianti (4)
  • Montalcino (2)
  • Montepulciano (2)
  • Monteriggioni (2)
  • Monteroni d'Arbia (2)
  • Monticiano (2)
  • Pienza (5)
  • Poggibonsi (1)
  • Radicofani (4)
  • Rapolano Terme (2)
  • San Casciano dei Bagni (5)
  • San Gimignano (1)
  • San Lorenzo a Merse (2)
  • Sarteano (8)
  • Siena (4)

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63 Holiday homes

Filters applied: Heated pool (63)

(2) Excellent 

1 / 21

Rapolano Terme / Serre di Rapolano

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £70 / night

£305 / week

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from £70 / night

1 / 6

Canonica a Cerreto - Pianella apartment sleeps 2

Castelnuovo Berardenga / Pianella

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
We have three apartments, all from the old Canonica (Rectory) where monks used to reside. They are a testimony to history, but are equipped with everything a modern traveler would require. Each apartment has, for instance, a large, fully-equipped kitchen, and wireless a  …see more

from £131 / night

£914 / week

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from £131 / night

1 / 15

Province of Siena / Gaiole in Chianti

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £63 / night

£435 / week

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from £63 / night

Featured properties

(10) Excellent 

1 / 24

Romantic Tuscan cottage, sleeps four, total priva

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Casa Daniela' is a well farm into a romantic country cottage. The house ( Total independent ) - in the surroundings of Casole d'Elsa, a medieval village with Etruscan origins – is located on a hill surrounded by a large olive grove and a pretty garden. Inside the ma  …see more

from £118 / night

£696 - £1000 / week

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from £118 / night

1 / 10

Rocche di Valiano 3 - Castelnuovo Berardenga gite sleeps 2

Province of Siena / Castelnuovo Berardenga

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Le Rocche di Valiano is an ancient village situated in the heart of Chianti area near Siena.The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards.The spacious bedro  …see more

from £64 / night

£445 / week

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from £64 / night

1 / 27

San Gimignano / Castel San Gimignano

1 2 3 nights min stay

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

from £53 / night

£366 / week

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from £53 / night

1 / 16

Villa Casella - Contignano villa sleeps 18

Radicofani / Contignano

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
For those in search of an exceptional and luxurious Italian retreat, Villa Casella is the perfect choice. The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside.The villa sleeps up to 19 in 8 very spacious bedr  …see more

from £2813 / night

£11250 / week

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from £2813 / night

1 / 10

Molino della Lodola - Rapolano Terme b&b sleeps 4

Province of Siena / Rapolano Terme

1 4 5 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 5 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
The “Molino della Lodola” was an ancient water-mill built in the XVIII century, carefully restored by the current owners who tried to make the ambient more fascinating, with the total respect of the natural background of the structure.Elegant surroundings, warm, wel  …see more

from £105 / night

£566 - £931 / week

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from £105 / night

1 / 15

Province of Siena / Radicofani

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
 …see more

from £70 / night

£392 / week

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from £70 / night

1 / 5

Province of Siena / Pienza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

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1 / 16

Castle Cottage (v011) - San Casciano dei Bagni cottage sleeps 6

Province of Siena / San Casciano dei Bagni

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 40 km; Swimming pool; Child friendly ;
The cottage is in the heart of the hamlet which is completely surrounded by ancient walls, and has a splendid view of the parish church and all the valley. It is independent and surrounded by a large garden. All the ceramics in the house were painted by the owner and ha  …see more

from £123 / night

£861 - £1105 / week

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from £123 / night

1 / 22

la lodola - Crete Senesi apartment sleeps 4

Asciano / Crete Senesi

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
In Lodola the guest enjoys reserve, relax and comfort, plunging into an absolutely bucolic environment. The oval swimming-pool with its wide sun- parlour is situated in the big surrounding park, where there is also a wide path for jogging and walking.The farmhouse is  …see more

from £105 / night

£731 / week

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from £105 / night

1 / 16

Villa - Asciano farmhouse sleeps 11

Province of Siena / Asciano

6 11 1 night min stay

  • 6 bedrooms
  • Sleeps 11
  • 1 night min stay
Key info: Nearest beach 90 km; Swimming pool; Child friendly ;
he beautiful master's villa has an austere Tuscan architectural structure, of some 600 square metres distributed on two floors.On the ground floor you will find the entrance, a large sitting room with Tuscan-style fireplace, a sitting-room, a dining room, a card ro  …see more

from £653 / night

£4696 / week

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from £653 / night

(2) Excellent 

1 / 12

Province of Siena / Monteriggioni

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
Key info: Nearest beach 70 km; Swimming pool; Not suitable for children;
 …see more

from £125 / night

£869 - £1212 / week

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from £125 / night

1 / 16

PODERE SANT'ALESSANDRO - Crete Senesi farmhouse sleeps 6

Asciano / Crete Senesi

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Child friendly ;
Podere Sant'Alessandro is an old Tuscan cottage with a panoramic view immersed in beautiful scenery, among woods, vineyards, medieval villages and castles. The structure has been just restored, but we didn't want to modify its original architectural characteri  …see more

from £157 / night

£974 - £1131 / week

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from £157 / night

1 / 24

Villa in Tuscany - Montepulciano villa sleeps 12

Province of Siena / Montepulciano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
The Poggio Golo holiday villa has been restored to its original splendour after long and careful renovation, giving you the possibility to savor the atmosphere of a holiday from past times in an old 17th century villa with original furniture and accessories. The well-tr  …see more

from £218 / night

£2131 - £3653 / week

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from £218 / night

(10) Excellent 

1 / 19

Rustic Tuscan holiday apartment rental with beautiful garden and shaded terrace, sleeps 4

Province of Siena / Monteroni d'Arbia

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Dotata di un salone con sala giochi e biblioteca e del servizio di biciclette gratuite in loco, la Villa Sant'Alberto offre case vacanza nel cuore delle Crete Senesi.Le sistemazioni, tutte caratterizzate da arredi in stile rustico, sono fornite di salotto a pianta  …see more

from £340 / night

£792 / week

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from £340 / night

1 / 20

Cypress Manor (V037) - Sarteano manor house sleeps 18

Province of Siena / Sarteano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
Beautifully renovated and furnished, luxury manor house with air conditioning in each room, underfloor heating, large paved stone patio that surrounds the whole house with pergola to eat outside and a laundry room. The house is divided as follows:.On the ground floor fo  …see more

from £1038 / night

£7261 - £14305 / week

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from £1038 / night

(2) Very Good 

1 / 17

Il Borgo del Grillo - Sarteano villa sleeps 50

Province of Siena / Sarteano

23 50 3 nights min stay

  • 23 bedrooms
  • Sleeps 50
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Il Borgo del grillo, originally registered as Borgo Fastelli in its 1765 Catasto Leopoldino entry (the local land registry of the time) is an historical abode which has been towering over the Val d'Orcia for centuries. Located in the western part of Monte Cetona, i  …see more

from £61 / night

£427 / week

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from £61 / night

1 / 52

Stunning private villa in Chianti wellness

Province of Siena / Castelnuovo Berardenga

8 16 7 nights min stay

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
The Piaggione of Serravalle, at a first glance, appears as a gem naturally cast on the highest ridges of the Chianti hills of Central Tuscany, and as a jewel it shines with its authentic flavors, ancient traditions and silent stillness. Shaded and enclosed by oak woods  …see more

from £361 / night

£2522 - £4870 / week

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from £361 / night

(1) Excellent 

1 / 21

"Casa Prisca" Borgo House in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
"Prisca House" is a wonderful first floor apartment lovingly restored to a high standard, set as a precious stone on the heart of Buonconvento Borgo.Tastefully and comfortable furnished, this apartment has a warm and friendly atmosphere and it offers guests a  …see more

from £70 / night

£609 - £853 / week

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from £70 / night

(9) Excellent 

1 / 20

Province of Siena / Poggibonsi

2 8 3 nights min stay

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £114 / night

£792 - £1644 / week

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from £114 / night

(2) Excellent 

1 / 40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car advised;
 …see more

from £109 / night

£774 - £2140 / week

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from £109 / night

1 / 31

Villa Colombaio - Asciano villa sleeps 9

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
As guests enter the property there is an entrance hall leading off to a living area on the right and large kitchen on the left. This area has an open plan feel to it. The kitchen is superbly equipped with everything guests could possibly need and want during their stay.  …see more

from £305 / night

£1696 - £3653 / week

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from £305 / night

(2) Excellent 

1 / 41

Province of Siena / Cetona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 28 km; Swimming pool;
 …see more

from £305 / night

£3348 / week

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from £305 / night

(4) Very Good 

1 / 43

Chianti house, Florence, Siena, Jacuzzi, Tuscany

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Child friendly ; Pet friendly;
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £47 / night

£272 - £609 / week

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from £47 / night

(2) Excellent 

1 / 20

Casa del Fico - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
The house forms part of the oldest wing of Le Bagnaie, a 300 year old farm on a secluded hilltop, which was converted into 8 privately owned houses in 1990. All are beautifully restored in traditional rustic style, with exposed beams, old terracotta floors and open fir  …see more

from £165 / night

£1150 - £1950 / week

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from £165 / night

1 / 18

Oak House (v022) - Sarteano villa sleeps 15

Province of Siena / Sarteano

7 15 7 nights min stay

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
A quiet country house, built between the XV and XVI centuries, full of atmosphere and immersed in the classical Sienese landscape of, oak and holm oak woods, olive groves, vineyards and fields of wheat. It is surrounded by lush vegetation and pastures where sheep graze.  …see more

from £273 / night

£1905 - £4574 / week

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from £273 / night

1 / 22

Villa Gaiole - Siena villa sleeps 13

Province of Siena / Siena

5 13 2 nights min stay

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside. Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visito  …see more

from £2533 / night

£8442 - £11255 / week

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from £2533 / night

1 / 9

Holiday House Sarteano - Sarteano house sleeps 4

Province of Siena / Sarteano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
Borgo Fastelli in its 1765 Catasto Leopoldino entry (the local land registry of the time) is an historical abode which has been towering over the Val d'Orcia for centuries. Located in the western part of Monte Cetona, it has a unique view of the valley below, which  …see more

from £174 / night

£1044 / week

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from £174 / night

1 / 27

Province of Siena / Sarteano

7 14 7 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
 …see more

from £957 / night

£6696 - £8870 / week

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from £957 / night

1 / 84

Villa Osservatorio - Tocchi villa sleeps 27

Monticiano / Tocchi

14 27 7 nights min stay

  • 14 bedrooms
  • Sleeps 27
  • 7 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Child friendly ;
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse.Villa Osservatorio  …see more

from £2768 / night

£19370 - £25827 / week

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from £2768 / night

1 / 24

Villa Palazzone - San Casciano dei Bagni villa sleeps 18

Province of Siena / San Casciano dei Bagni

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
"Villa Palazzone" is a charming country house set in the heart of a large estate of 153 hectares. The property has been completely renovated and upgraded with all modern conveniences.It is characterized by a main house with 3 apartments and 3 suites annexes. The gue  …see more

from £283 / night

£1731 - £2914 / week

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from £283 / night

1 / 17

Amazing tuscan villa in front of Brunello's hills

Province of Siena / Monticiano

2 4 5 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min stay
Key info: Nearest beach 48 km; Swimming pool; Child friendly ;
It is a peacefull south-east oriented villa located in the hills of Tuscany between Siena and Porto Santo Stefano. The villa dominates the valley. The landscape is astonishing and Villa Banfi, the best Brunello's producer is the characterizing element of the background.  …see more

from £183 / night

£1218 / week

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from £183 / night

1 / 19

The Tower (v026) - Sarteano villa sleeps 11

Province of Siena / Sarteano

5 11 7 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
Ground floor: a living room with fireplace and access to the garden and a stone paved terrace, study / TV room with a sofa bed that can become a comfortable single room with en-suite bathroom with shower, large dining room with fireplace and access to the covered terrac  …see more

from £716 / night

£5009 - £8453 / week

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from £716 / night

1 / 5

Agriturismo with heated pool - Monteroni d'Arbia villa sleeps 16

Province of Siena / Monteroni d'Arbia

5 16 3 nights min stay

  • 5 bedrooms
  • Sleeps 16
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Air conditioning;
Five stars tripadvisor rated since years! Air conditioning and heated pool perfect location near Siena. You can either rent a single self catering apartment or the whole villa and you will be welcomed by Filippo and Rachel the owners! In the villa large beautiful common  …see more

from £818 / night

£5044 / week

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from £818 / night

1 / 20

The Heights (v004) - Sarteano villa sleeps 10

Province of Siena / Sarteano

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
Ground floor: living room with fireplace and access to the terrace with pergola and large stone fireplace, dining room with access to the outdoor dining area, kitchen, a double room with en suite bathroom with bath, wardrobe, closet with washer and dryer, terrace with p  …see more

from £551 / night

£3853 - £7261 / week

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from £551 / night

1 / 14

Province of Siena / Radicofani

10 24 Min stay varies

  • 10 bedrooms
  • Sleeps 24
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car not necessary;
 …see more

from £627 / night

£3305 - £3827 / week

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from £627 / night

1 / 52

Villa Manafiore - Monticchiello villa sleeps 9

Pienza / Monticchiello

6 9 7 nights min stay

  • 6 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; No pets allowed;
This marvelous villa occupies a gently sloping site facing west across the fertile Orcia Valley towards the majestic Amiata Mountain. Sheltered to the east by a woodland and surrounded by well-tended gardens, the property includes several acres of vineyards and olive  …see more

from £839 / night

£5870 / week

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from £839 / night

1 / 18

Borgo del Grillo - Sarteano apartment sleeps 6

Province of Siena / Sarteano

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Nearest beach 25 km; Swimming pool; Child friendly ;
In the heart of Valdorcia, on the west side of Mt Cetona, our “Borgo” has been dominating for more than 400 years this exceptional valley that the UNESCO declared to be one of humankind’s treasures. Apartment with huge sitting-room with fireplace, equipped kitche  …see more

from £174 / night

£1131 / week

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from £174 / night

Top Destination reviews

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool
What a great place to stay

My wife and I, along with our friends from Edinburgh, rented for a week at the end of June. What great accommodation, well presented, and the gardens, pool etc was a wonderful environment to relax in. Easy travelling to all the major Tuscan sights, … see more
COSOLI CHARMING HISTORICAL VILLA IN CHIANTI
Tuscan Heaven

Cosoli is a beautiful villa in a stunning location. It was a superb family holiday location. thanks. … see more
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
Podere Lo Spadino
What a wonderful place in Italy

We stayed now the second time in Podere Lo Spadino, we are a Group with 8 peoples, and everything in this house is amazing. The whole house, the garden, the pool and of course Barbara with her Family, they are helpful and very friendly and nice. We … 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
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

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