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

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Province of Siena

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4,394 Holiday homes

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

(1) Excellent 

20

Caprera holiday apartment rental

Siena / Caprera

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 100 km
  • Child friendly
  • Air conditioning
Suite Le Camelie has all the comfort you would find in a hotel. It is at the same time a real Tuscany home with a local decor and feeling, surrounded by luxurius gardens and olive trees. Ideal location for visiting both Siena and the country side.  …see more

from £71 / night

£439 - £483 / week

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from £71 / night

(1) Very Good 

21

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Air conditioning

 …see more

from £140 / night

£977 / week

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from £140 / night

(5) Very Good 

21

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 km
  • Swimming pool
  • Child friendly

 …see more

from £110 / night

£641 - £974 / week

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from £110 / night

(1) Very Good 

20

Province of Siena / Pienza

2 4 2 nights min

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

 …see more

from £115 / night

£615 / week

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from £115 / night

(1) Very Good 

39

Farmhouse rental in Larniano with shared pool

San Gimignano / Larniano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Silence, privancy  …see more

from £176 / night

£1185 - £1930 / week

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from £176 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £49 / night

£316 - £378 / week

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from £49 / night

(1) Excellent 

14

Province of Siena / Poggibonsi

2 4 1 night min

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

 …see more

from £44 / night

£308 / week

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from £44 / night

(5) Very Good 

24

Holiday apartment rental

Siena / Val di Merse

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
Warm and welcoming, ten kilometres away from Siena, this apt is set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect & designer. The very best of the Tuscan tradition can be enjoyed here.<br />Ideal f  …see more

from £176 / night

£965 - £1229 / week

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from £176 / night

(1) Excellent 

22

Province of Siena / Gallina

2 6 Min stay varies

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

 …see more

from £141 / night

£983 / week

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from £141 / 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 £88 / night

£422 - £527 / week

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from £88 / night

(2) Very Good 

18

Holiday farmhouse with shared pool in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
“Quiet, relaxing and beautiful location, with great pool and comfortable accommodation.” We stayed in the ground floor 2 bedroom farmhouse apartment, away from the 'village'. It was a beautiful setting, with great views. The outdoor seating/dining furn  …see more

from £88 / night

£527 - £702 / week

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from £88 / night

(6) Excellent 

23

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“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  …see more

from £308 / night

£1360 - £2193 / week

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from £308 / night

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £84 / night

£430 - £1000 / week

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from £84 / 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 £175 / night

£1100 - £1600 / 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 £101 / night

£702 - £1097 / week

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from £101 / night

29

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
This lovely country house with pool in Tuscany is located at 1.5km from the beautiful medieval village of Torrita di Siena, in the heart of Val di Chiana, only 15 km from Pienza and Montepulciano, and 48 km from Siena. Situated on a knoll, the 18th-century farmhouse is  …see more

from £53 / night

£369 - £702 / week

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from £53 / night

(2) Very Good 

29

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 relaxing<br />The pool and the gar  …see more

from £176 / night

£1229 - £1843 / week

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from £176 / night

100

Holiday villa with swimming pool 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 70 km
  • Swimming pool
  • Child friendly
Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning views of the Tuscan landscape. Perfect for families and large groups of friends.  …see more

from £439 / night

£3071 - £4167 / week

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from £439 / night

(8) Excellent 

12

Province of Siena / Monteriggioni

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £53 / night

£351 / week

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from £53 / night

(5) Excellent 

24

Province of Siena / Radda in Chianti

2 5 5 nights min

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

 …see more

from £84 / night

£584 - £707 / week

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from £84 / night

(16) Very Good 

27

Holiday apartment in Sant Andrea a Montecchio

Siena / Sant Andrea a Montecchio

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Child friendly
  • Car not necessary
“Reality of a dream!” I was looking for a quiet week with a beautiful panorama not far from Siena, to enjoy after the Palio and before participating in an intensive celebration later in July within Siena. I studied the information on Sant'Andrea a Mon  …see more

from £53 / night

£308 - £527 / week

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from £53 / night

22

Holiday villa rental

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Casale Reggello is located in the gently rolling Tuscan hills, between the wonderful towns of Pienza and Montepulciano, just a short distance from the thermal baths of Bagno Vignoni. Reggello is a single House with 8/10 beds and as its own swimming pool and surrounding  …see more

from £301 / night

£2106 - £3422 / week

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from £301 / night

20

Holiday farmhouse rental

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 44 km
  • Swimming pool
  • Child friendly
Wonderful Tuscan villa with pool.  …see more

from £361 / night

£2527 - £6509 / week

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from £361 / night

23

Holiday villa with swimming pool in Cetona

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The villa is located in the southermost corner of Tuscany on top of a hill facing Cetona. The views are breathtaking and stretch as far as Città delle Pieve and Orvieto. A short walk (1km) takes guests to the lovely medieval town of Cetona, where they can get fre  …see more

from £226 / night

£1579 - £3158 / week

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from £226 / night

(14) Excellent 

24

San Gimignano holiday villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
“Beautiful!” Four of us stayed here in October 2012, the house is beautiful and immaculately maintained as are the gardens. Unfortunately the weather wasn't on our side so we didn't spend as much time in the garden as we'd have liked but you could spe  …see more

from £71 / night

£483 - £1579 / week

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from £71 / night

(1) Excellent 

6

Province of Siena / Castiglione D'Orcia

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Ski

 …see more

from £44 / night

£308 / week

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from £44 / night

15

Holiday apartment in Larniano

San Gimignano / Larniano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
Lovely Two-roomed apartment (55 mq), 2-4 beds, inside San Gimignano. In a central position, but also surrounded by a rare and precious silence, our apartments offer the unique feeling of an ancient building with all the comfort of modern amenities.<br />Car parkin  …see more

from £78 / night

£544 / week

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from £78 / night

25

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 km
  • Swimming pool
  • Child friendly

 …see more

from £115 / night

£799 / week

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from £115 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £170 / night

£1404 - £2461 / week

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from £170 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £176 / night

£1009 - £2895 / week

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from £176 / night

8

Apartment rental in Montepulciano

Province of Siena / Montepulciano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Private garden
We have magnificent views, over the Val d'Orcia, Pienza, Montalcino, the Val Di Chiana Valley with its three lakes (Trasimeno, Chiusi and Montepulciano). Montepulciano is only 4 km far from here. You can easily reach the most famous cities of Tuscany and Umbria<  …see more

from £115 / night

£439 - £650 / week

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from £115 / night

32

Farnetella holiday villa rental

Sinalunga / Farnetella

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Beautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and services.  …see more

from £176 / night

£1229 - £2281 / week

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from £176 / night

23

Province of Siena / Poggibonsi

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £79 / night

£455 - £584 / week

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from £79 / night

(1) Very Good 

25

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
Stunning apartments for holiday rental in Torrita di Siena, near Pienza and Montepulciano  …see more

from £51 / night

£351 - £667 / week

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from £51 / night

13

Holiday chalet in Valiano

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Apartment with living-dining area, kitchen corner , double bedroom , bathroom with shower. TV SAT, iron and iron board, freezer, oven, high chair.  …see more

from £106 / night

£746 / week

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from £106 / night

(1) Excellent 

8

Province of Siena / Strove

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

 …see more

from £44 / night

£308 / week

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from £44 / 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 £351 / night

£2018 - £3509 / week

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from £351 / night

47

Province of Siena / San Gimignano

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Nearest beach 50 km
  • Child friendly
  • Private garden

 …see more

from £61 / night

£343 / week

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from £61 / night

23

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa in the heart of Tuscany with private pool, stunning views!  …see more

from £176 / night

£1229 - £1843 / week

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from £176 / night

(2) Very Good 

18

Holiday apartment in Sarteano

Province of Siena / Sarteano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
“good location & helpful landlord” Sarteano is a great location for seeing the rest of Tuscany and for experiencing "la dolce vita" in a small town. The people of Sarteano are very nice and helpful. The owner, Leonardo was especially helpful wit the a  …see more

from £53 / night

£255 / week

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from £53 / night