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

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Province of Siena

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4,219 Holiday homes

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

100

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
These apartments can host from 2 to 6 guests in apartments fitted with living/dining room, kitchen and 1 to 3 bedrooms. These apartments with views share a restaurant and a swimming pool.  …see more

from £102 / night

£585 - £895 / week

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from £102 / night

(11) Very Good 

65

Province of Siena / San Quirico d'Orcia

5 4 2 nights min

  • 5 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £56 / night

£339 - £636 / week

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from £56 / night

(20) Excellent 

49

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly
Cottage view on San Gimignano country house countryside<br />The cottage is provided with baby bed and bay chair.Pets: maximum 2 (small)  …see more

from £51 / night

£356 / week

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from £51 / night

(2) Excellent 

33

Province of Siena / Casole d'Elsa

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

 …see more

from £145 / night

£839 - £2492 / week

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from £145 / night

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has  …see more

from £387 / night

£2318 - £4003 / week

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from £387 / night

9

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Ask about pets

 …see more

from £60 / night

£382 / week

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from £60 / night

20

Villa rental in Val d'Orcia with swimming pool

Montalcino / Val d'Orcia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Villa Bandini is located only 300 meters from the hamlet of Lucignano d’Asso on top of a hill on the border between the Val d’Orcia and the Sienese clay hills. Lucignano d’Asso is a medieval ancient hamlet which, since the XV century, has belonged to t  …see more

from £398 / night

£2783 / week

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from £398 / night

100

Siena holiday apartment rental

Province of Siena / Siena

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

from £144 / night

£1003 - £1418 / week

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from £144 / night

15

Apartment rental in Montalcino with shared pool

Province of Siena / Montalcino

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Montecaprili is located at less than 10 km from Montalcino on the way to the famous abbey of Sant'Antimo. It's an old farm house set on top of a hill, finely restored and divided in 5 spacious apartments, all featuring authentic Tuscan furnishings and modern a  …see more

from £234 / night

£1526 / week

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from £234 / night

25

Holiday tower with swimming pool in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Torre Romantic View Lake Vineyards Olive Groves Swimming Pool Wine Relax Families Childrens Peacefull<br />The Torre is 1,5 km from Radda enjoing all the facilities of a charming small village. Full of Activities!  …see more

from £119 / night

£806 / week

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from £119 / night

100

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Villa Nobile is a recently restored farmhouse on a wine and olive oil producing estate very near Montepulciano. The privileged position of the villa atop a hill offers magnificent views and a private swimming pool adds to the relaxing holiday mood.  …see more

from £255 / night

£1780 - £3051 / week

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from £255 / night

(2) Excellent 

13

Holiday apartment in Rapolano Terme

Province of Siena / Rapolano Terme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden
L'appartamento nasce dalla ristrutturazione di un ovile al piano terra, ha spesse e antiche mura, cucina attrezzata e luminosa con porta a vetri sul giardino, una zona armadi antistante il bagno, molto curato, un ampio salone con camino e seconda porta sull'es  …see more

from £30 / night

£208 / week

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from £30 / night

(12) Excellent 

24

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
“Into the bliss!” The moment we arrived at the Autostazione di Montepulciano, Luca greeted us with a big smile and and an open heart that made this trip so particularly memorable. His flat on up on the edge of the hill was as described and better. It c  …see more

from £98 / night

£594 - £736 / week

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from £98 / night

100

Holiday villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 18 2 nights min

  • 9 bedrooms
  • Sleeps 18
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This villa has a swimming pool in its gardens and offers accommodation for 18 guests in a building with a living room, dining area, kitchenette, bedroom and bathroom each.  …see more

from £933 / night

£6356 - £6695 / week

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from £933 / night

(2) Very Good 

27

San Gusme holiday villa rental

Castelnuovo Berardenga / San Gusme

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Private garden
“wonderful and peaceful place” San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will return one day, for sure  …see more

from £181 / night

£1263 - £1687 / week

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from £181 / night

(6) Very Good 

19

Holiday villa with swimming pool in Siena

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
Villa Le Tolfe is so close to Siena you can almost touch it (only 3 kilometres away). With stunning views and beautiful antique gardens this villa is perfect for relaxed stress free holidays. The house is built on top of a hill covered with olive groves and vineyards.  …see more

from £152 / night

£1060 - £2111 / week

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from £152 / 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 £120 / night

£839 - £1628 / week

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from £120 / night

16

Holiday apartment rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful country house situated just a stone's throw away from San Gimignano, an attractive medieval town with a unique collection of towers and winding lanes set in the heart of the Tuscan countryside. This farmhouse enjoys spectacular views over a picturesque ru  …see more

from £130 / night

£908 - £1484 / week

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from £130 / night

(4) Very Good 

7

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from £50 / night

£350 / week

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from £50 / night

31

San Gimignano / Castel San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £77 / night

£551 / week

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from £77 / night

18

Province of Siena / Casole d'Elsa

2 6 Min stay varies

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

 …see more

from £85 / night

£594 / week

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from £85 / night

21

Castelnuovo Berardenga / Pianella

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(8) Excellent 

7

Province of Siena / Rosia

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from £59 / night

£348 / week

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from £59 / night

24

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Campiglia dei Foci

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
These lovely rental apartments in Tuscany are located on a plateau in the heart of the Chianti countryside at only 5 km from Colle Val d'Elsa, internationally renowned for the production of crystal glassware and art. Surrounded by vineyards and olive groves, the re  …see more

from £66 / night

£462 - £780 / week

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from £66 / night

(1) Excellent 

13

Province of Siena / Chianciano Terme

2 3 2 nights min

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

 …see more

from £39 / night

£255 / week

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from £39 / night

24

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£831 / week

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from £119 / night

24

Poggibonsi holiday villa rental

Province of Siena / Poggibonsi

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
This beautiful villa in Tuscany, Italy, sleeps 2 people, so it is perfect for honeymoons. The accommodation offers a perfect holiday stay.  …see more

from £54 / night

£373 - £602 / week

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from £54 / night

(4) Excellent 

53

Holiday apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Child friendly
  • Ask about pets
Casa Arianna self-cathering apartment in Montegabbro, a very little 12th century village in the hearth of Tuscany with Etruscan and Roman traces. Ideal for families seeking relaxation.<br />Private area outside to enjoy the quite of the village and the Tuscan coun  …see more

from £51 / night

£297 - £416 / week

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from £51 / night

(3) Excellent 

22

Villa rental in Siena with swimming pool

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level)  …see more

from £339 / night

£1950 - £3390 / week

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from £339 / night

(1) Excellent 

13

Province of Siena / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly

 …see more

from £77 / night

£509 - £551 / week

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from £77 / night

(5) Excellent 

26

Holiday cottage with swimming pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly
Charming cottage with private pool and pet-friendly near Siena  …see more

from £64 / night

£424 - £1272 / week

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from £64 / night

100

Holiday villa with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
This pleasant house, with 6 bedrooms and 6 bathrooms can host 12 people, so it is perfect for a large group of friends. Located in Lazio Italy, this house offers a swimming Pool, an internet Connection, a pet friendly space, disabled access .  …see more

from £356 / night

£1373 - £2975 / week

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from £356 / night

100

Holiday apartment in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This beautiful estate in Tuscany includes both a b&b offering a range of lovely rooms and suites as well as fabulous apartments. These all have the outdoor swimming pool, tennis court and restaurant, and other facilities at their disposition.  …see more

from £106 / night

£736 - £1045 / week

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from £106 / night

10

Province of Siena / Ville di Corsano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

(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

(7) Excellent 

7

Province of Siena / Rosia

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £76 / night

£416 / week

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from £76 / night

22

Province of Siena / Torrita di Siena

7 11 7 nights min

  • 7 bedrooms
  • Sleeps 11
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £309 / night

£2162 / week

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from £309 / night

(4) Excellent 

96

Holiday villa in Monticiano

Province of Siena / Monticiano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Ideal family and wedding Tuscan villa with private pool very close to San Galgano Abbey, Siena, Tuscany. Suitable for groups, families and children. Tucked away from the main vuillage, not isolated. All amenities in the village, just 3 minutes' walk away. Siena 25  …see more

from £933 / night

£6356 - £10326 / week

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from £933 / night

35

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£509 - £653 / week

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from £77 / night

(2) Excellent 

7

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from £51 / night

£356 / week

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from £51 / night