Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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Province of Siena

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4,392 Holiday homes

Travellers going to Province of Siena are booking June dates now. Secure your holiday home today and have the perfect trip.

(21) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

 …see more

from £48 / night

£292 - £422 / week

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from £48 / night

(4) Excellent 

24

Cottage rental in Casole d'Elsa with swimming pool

Province of Siena / Casole d'Elsa

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
“Beautiful location” The villa is lovely & bigger than it looks in the photos! I would recommend it although there are a couple of grumbles! The villa is definately not walking distance to the town. It is down a long, long gravel track, so beautiful  …see more

from £81 / night

£566 - £1218 / week

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from £81 / night

(7) Very Good 

22

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from £84 / night

£509 / week

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from £84 / 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 £472 / night

£3305 - £4261 / week

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from £472 / night

(2) Very Good 

14

Holiday apartment in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag  …see more

from £61 / night

£222 - £457 / week

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from £61 / night

(1) Excellent 

16

Province of Siena / Sarteano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £261 / night

£1392 - £1740 / week

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from £261 / night

(3) Excellent 

24

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Pet friendly

 …see more

from £47 / night

£331 - £492 / week

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from £47 / night

22

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £94 / night

£408 - £1114 / week

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from £94 / night

(1) Excellent 

21

Holiday apartment in Tognazza

Province of Siena / Tognazza

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
“Great location to explore Tuscany from.” Lovely apartment with everything you need to be comfortable. Location was great for exploring Tuscany. Saverio (host) was also very helpful. Would recommend highly.  …see more

from £35 / night

£244 / week

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from £35 / night

48

Fort letting in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

from £108 / night

£746 - £828 / week

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from £108 / night

100

Holiday apartment in Guazzino

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
Charming apartment located in Bettolle, this lovely holiday apartment is ideal for a couple who wish to discover Tuscany and Umbria from a central location.  …see more

from £49 / night

£308 - £492 / week

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from £49 / night

(2) Excellent 

35

Holiday farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Quintessential Tuscany!” This is a wonderfull house with very beautiful surroundings, particularly the terrasse and view of the Tuscan landscape and also swimmingpool and outdoor area with olive trees, apples, and other fruits! perfect for children. G  …see more

from £66 / night

£457 / week

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from £66 / 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 £47 / night

£272 - £609 / week

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from £47 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this stunning accommodation is the perfect place for your holidays. The accommodation offers: a swimming Pool, air Conditioning, a pet friendly space .  …see more

from £1597 / night

£11181 - £16150 / week

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from £1597 / night

(1) Excellent 

9

Province of Siena / Pienza

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

 …see more

from £183 / night

£618 - £1000 / week

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from £183 / night

(33) Excellent 

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Fabulous holiday and accommodation” We stayed at this apartment in June this year. The apartment was really well fitted out and spotlessly clean, the oven looked like it had never been used !! The facilities were great and the location is lovely, it i  …see more

from £87 / night

£479 - £740 / week

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from £87 / night

(5) Very Good 

49

Montisi holiday fort rental

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Romantic and charming 14th century fortress. Very authentic medieval atmosphere. Strategically located between Val d'Orcia and Crete Senesi, close to Montalcino, Montepulciano, Pienza and Siena. Shops at walking distance. Organic wine and extra virgin olive oil.  …see more

from £108 / night

£746 - £828 / week

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from £108 / night

(3) Excellent 

22

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Rustic and romantic apartment for up to 7 people (5+2) with swimming pool (1 May-1 Oct), four-poster beds, rustic, classic furniture, air cond, garden, terrace, private sunbeds / umbrellas.Situated near San Gimignano with breathtaking views all the way to Volterra<b  …see more

from £37 / night

£253 - £861 / week

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from £37 / night

(1) Excellent 

28

Apartment rental in Torrita di Siena with shared pool

Province of Siena / Torrita di Siena

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

from £48 / night

£331 - £592 / week

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from £48 / night

(4) Very Good 

17

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£348 - £809 / week

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from £61 / night

10

Valiano holiday apartment rental

Montepulciano / Valiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Guests will find inspiring spaces for reading and relaxing, a beautiful swimming pool, a panoramic terrace, solarium, barbeque and a bread-oven with covered area.<br />Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

from £87 / night

£418 - £522 / week

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from £87 / night

(12) Excellent 

69

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 £412 / night

£2883 - £4435 / week

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from £412 / night

(2) Excellent 

21

Holiday apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • 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 £61 / night

£427 / week

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from £61 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £79 / night

£479 - £505 / week

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from £79 / night

(10) Excellent 

10

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

 …see more

from £40 / night

£548 - £2283 / week

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from £40 / night

(4) Excellent 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from £70 / night

£479 - £600 / week

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from £70 / night

(6) Very Good 

25

Province of Siena / Monteriggioni

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £48 / night

£314 - £509 / week

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from £48 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 60 km
  • Child friendly
  • Pet friendly
“What you imagine when you think "Tuscany"!” We stayed in La Verbena, and it was amazing. Podere Sortoiano is about 15 minutes out of Siena, but it is so worth it to stay out of the city! It's incredibly quiet and relaxing, and the stars are unlike any  …see more

from £48 / night

£340 - £431 / week

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from £48 / night

24

Holiday apartment rental

Province of Siena / Casole d'Elsa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Large apartment of 105 sqm on the second floor of the farmhouse which consists of an entrance, a fully equipped kitchen, a large sitting room with double divan bed and dining area, a small storeroom, a double bedroom with built-in wardrobe and a bathroom  …see more

from £157 / night

£983 - £1861 / week

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from £157 / night

19

Siena / Gracciano di Colle Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £61 / night

£653 - £914 / week

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from £61 / night

(3) Excellent 

25

Province of Siena / Vivo d'Orcia

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 70 km
  • Ski
  • Child friendly

 …see more

from £61 / night

£392 / week

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from £61 / night

(12) Very Good 

28

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

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Toscany at its best at Radda in Chianti property Villa PetrAlexa” The property itself is wonderfully placed between woods and a vinery in the picturesque Chianti area near Radda. The hospitality we have experienced was outstanding in the mean that you  …see more

from £179 / night

£1253 - £2087 / week

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from £179 / night

(8) Excellent 

24

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa and location shame about the weather” The villa was fantastic with extremely hospitable hosts. Grandma provided us with her fantastic home made cake and olive oil. Grandad provided us with home grown beans and lettuce. The Villa is sit  …see more

from £140 / night

£957 / week

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from £140 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Fabulous place to stay with a group of friends or family.” My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out in the cute to  …see more

from £300 / night

£1500 - £2000 / week

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from £300 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

 …see more

from £90 / night

£700 / week

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from £90 / night

(2) Very Good 

19

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Air conditioning
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite i  …see more

from £144 / night

£1005 / week

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from £144 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment Siena centre-Central, ground floor, easy accessible, cosy, tastefully furnished. Double bedroom, fully equipped kitchen with sofa bed for two guests, large bathroom with shower, free WIFI, sat Tv, air conditioning.<br />Upon request as extra servic  …see more

from £39 / night

£271 / week

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from £39 / night

15

Province of Siena / Castellina In Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 km
  • Child friendly
  • Private garden

 …see more

from £48 / night

£335 / week

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from £48 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £105 / night

£496 - £592 / week

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from £105 / night

(1) Excellent 

18

Sinalunga holiday apartment rental

Province of Siena / Sinalunga

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
In the heart of the countryside only 40 minutes from Siena five beautiful apartments have been made by restoring an old Tuscan country house set on a hillside with views all around. Each apartment retains its fascinating original characteristics. A courtyard around the  …see more

from £89 / night

£618 - £1087 / week

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from £89 / night