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Province of Siena

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1,718 Holiday homes

Filters applied: Dishwasher (1,720)

(4) Excellent 

18

Province of Siena / Siena

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden

 …see more

from £43 / night

£295 / week

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from £43 / night

(12) Excellent 

49

Holiday villa in San Giovanni d'Asso

Province of Siena / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“Gorgeous villa in Tuscany” This is a gorgeous villa in the tuscan countryside. The villa was beautiful, spotless and had everything we needed. It is right next to the small town of San Giovanni D'Osso. My 16-year-old loved it as well. While we day-tri  …see more

from £456 / night

£3194 - £4118 / week

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from £456 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a lovely villa set in Tuscany Italy. It has 2 bedrooms and 2 bathrooms, and it is perfect for those who are looking for a unique experience. This property features: a swimming Pool, air Conditioning .  …see more

from £164 / night

£958 - £1598 / week

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from £164 / night

(3) Very Good 

20

Siena holiday apartment rental

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Elegant and sophisticated apartment carefully restored, with frescoed ceilings and walls and tastefully furnished large rooms, set a short walk from Piazza del Campo, the heart of the Italy’s loveliest medieval cities, Siena.  …see more

from £127 / night

£757 / week

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from £127 / night

(3) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan apartment with shared swimming pool, not far from Siena. It sleeps up to 4 guests. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.A heaven of peace in the heart of the Montagnola Se  …see more

from £76 / night

£505 - £925 / week

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from £76 / night

24

Holiday villa rental

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 val...  …see more

from £175 / night

£1222 - £2069 / week

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from £175 / night

(6) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fabulous house in glorious location” Lovely welcome from Elsa - an fantastic traditional meal mid week. The house was beautiful and spacious with everything you could need. Children - 8, 10, 12, 13 loved house and garden - especially the tortoise!  …see more

from £97 / night

£673 - £1051 / week

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from £97 / night

(12) Excellent 

78

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £398 / night

£2786 - £4286 / week

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from £398 / night

(4) Excellent 

18

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is furnished tastefully and with exclusive period furniture, fireplace, Sky TV, independent heating, external private space. Park, scenic swimming pool.  …see more

from £101 / night

£463 - £715 / week

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from £101 / night

(6) Very Good 

43

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 £46 / night

£263 - £589 / week

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from £46 / night

(2) Very Good 

10

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxingThe pool and the garden are not  …see more

from £135 / night

£925 - £1765 / week

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from £135 / night

24

Holiday villa rental

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
<p>Siena countryside family villa – Conveniently located south of Siena, Biancaserena is a modern villa surrounded by the typical, idyllic Tuscan landscape.</p>  …see more

from £282 / night

£1970 - £3940 / week

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from £282 / night

20

Province of Siena / Chiusdino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £361 / night

£2522 - £3194 / week

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from £361 / night

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

11 26 7 nights min

  • 11 bedrooms
  • Sleeps 26
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Hunting lodge of the second half of the XVIII century, surrounded by a park of oaks and cypress trees. Beautiful infinity swimming pool (6x12 m).  …see more

from £663 / night

£4639 - £5412 / week

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from £663 / night

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £229 / night

£1597 - £3360 / week

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from £229 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £901 / night

£6303 - £8824 / week

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from £901 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £47 / night

£303 - £421 / week

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from £47 / night

24

Holiday villa letting

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

from £559 / night

£3908 / week

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from £559 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect and plaisant location to explore Tuscany” We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but  …see more

from £165 / night

£1000 - £1600 / week

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from £165 / night

(1) Excellent 

21

Province of Siena / Cetona

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Child friendly

 …see more

from £177 / night

£1236 / week

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from £177 / night

4

Province of Siena / Radicondoli

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Nearest beach 55 km
  • Suitable for children age 5+
  • Private garden

 …see more

from £59 / night

£421 / week

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from £59 / night

(4) Excellent 

17

Holiday home in Cetona

Province of Siena / Cetona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about pets
“A real tase of Tuscany” If you're looking for an authentic old town stay then you'll be very happy. Great location in the old town and so close to lots small towns to explore. Train to Florence as a day trip. Large rooms cumfy beds and amazing views f  …see more

from £59 / night

£412 / week

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from £59 / night

23

Holiday apartment with shared pool in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This 65sqm apartment is on one floor only and consists of a sitting room with dining area, fireplace and double divan bed, a small fully equipped kitchen, a double bedroom with a bathroom fitted with shower, a twin bedroom and a bathroom with both bathtub and shower.  …see more

from £85 / night

£505 - £1345 / week

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from £85 / night

(2) Excellent 

16

Province of Siena / Siena

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from £244 / night

£1673 - £8824 / week

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from £244 / night

28

Sinalunga holiday villa rental

Province of Siena / Sinalunga

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies.  …see more

from £119 / night

£832 - £1614 / week

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from £119 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Castiglione D'Orcia / Gallina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

from £181 / night

£1261 - £2059 / week

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from £181 / night

19

Siena holiday apartment rental

Province of Siena / Siena

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Beautiful Tuscan apartment with shared swimming pool, not far from Siena. It sleeps up to 8 guests. It is an ideal place for families to spend a relaxing holiday far from town noises, among the peace of the countrside.A heaven of peace in the heart of the Montagnola Se  …see more

from £152 / night

£883 - £1597 / week

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from £152 / night

(6) Very Good 

20

Holiday villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill  …see more

from £169 / night

£900 - £2269 / week

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from £169 / night

100

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

8 14 7 nights min

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people.  …see more

from £721 / night

£5043 - £8404 / week

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from £721 / night

(11) Excellent 

33

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
“Great stay!” Luca was wonderful to work with. He gave us directions on how to meet him and took us to the apartment to unload the car then helped us find a parking spot. Apartment was very nice, comfortable and close to the city center. Luca was alwa  …see more

from £76 / night

£437 - £532 / week

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from £76 / night

(1) Very Good 

30

Holiday home in Siena

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Child friendly
  • Private garden
Only 20km outside the charming city of Siena, my cottage is emerging in a forest on top of a hill. Ideal for biking and hiking. My cottage is exclusive for you! Perfect for enjoyable holidays or for a working context. WiFi-connection. A picturesque mosaic of fields an  …see more

from £55 / night

£379 - £496 / week

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from £55 / night

(5) Excellent 

23

Holiday apartment in Pienza

Province of Siena / Pienza

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
“Fantastic place - great selection of restaurants” Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to  …see more

from £118 / night

£824 / week

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from £118 / night

15

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £185 / night

£690 - £1093 / week

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from £185 / night

100

Montalcino holiday villa rental

Province of Siena / Montalcino

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a stunning villa set in Tuscany Italy. It has 4 bedrooms and 3 bathrooms, and it is ideal for those who are looking for a memorable experience. This property features: a swimming Pool, air Conditioning .  …see more

from £235 / night

£1642 - £2695 / week

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from £235 / night

(1) Excellent 

12

Province of Siena / Pievescola

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 74 km
  • Child friendly
  • Pet friendly

 …see more

from £76 / night

£530 / week

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from £76 / night

(1) Very Good 

11

Province of Siena / Gaiole in Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from £68 / night

£404 - £807 / week

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from £68 / night

(2) Excellent 

21

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 guest  …see more

from £59 / night

£631 - £866 / week

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from £59 / night

(2) Excellent 

24

Province of Siena / Colle di Val d'Elsa

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £110 / night

£648 - £967 / week

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from £110 / night

15

Holiday farmhouse accommodation

Province of Siena / Cetona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Typical Italian agritourism with swimming pool.  …see more

from £128 / night

£891 - £1227 / week

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from £128 / night

(4) Excellent 

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A 17th century stone hamlet situated in one of the most wonderful position of Tuscany. The apartment is characterised by good taste and warmth, equipped with a fireplace and elegantly furnished with furniture from the era. Park, scenic swimming pool.  …see more

from £127 / night

£530 - £900 / week

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from £127 / night