Apartments and villas with parking in Province of Siena

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Province of Siena

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2,315 Holiday homes

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

(1) Average 

25

Province of Siena / San Quirico d'Orcia

1 2 Min stay varies

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

 …see more

from £103 / night

£718 / week

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from £103 / night

22

Montepulciano holiday villa rental

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
TUSCANY MONTEPULCIANO PIENZA ANCIENT COUNTRY FARM ENTIRE OR HALF PROPERTY WEEKLY RENT ONLY groups of 4-10 welcome<br />heating upon request extra fee to be paid at check out according to gasoline cube meters used  …see more

from £257 / night

£1795 / week

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from £257 / night

6

Holiday apartment with shared pool in Casole d'Elsa

Casole d'Elsa / Monteguidi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Our APARTMENTS and ONE-ROOM APARTMENTS are located in the two main buildings of the Borgo; they have simple and functional furnishings, they are warm and inviting, and all rooms have their original timbered ceilings and Tuscan terracotta.  …see more

from £95 / night

£560 - £1094 / week

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from £95 / night

Featured properties

(9) Excellent 

39

Province of Siena / Vivo d'Orcia

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Ski
  • Child friendly
  • Ask about pets

 …see more

from £85 / night

£526 - £933 / week

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from £85 / night

24

Holiday villa rental

Province of Siena / Cetona

10 20 2 nights min

  • 10 bedrooms
  • Sleeps 20
  • 2 nights min
  • Ask owner if suitable for children
Villa Bello is a typically idyllic Tuscan farmhouse. Carefully restored and surrounded by beautiful Tuscan landscape, it's only 4 km from the picturesque village of Cetona.  …see more

from £1040 / night

£2970 - £4134 / week

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from £1040 / night

16

Farmhouse rental in Pienza with shared pool

Province of Siena / Pienza

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Monticchiello with 3 bedrooms sleeps 6  …see more

from £100 / night

£589 - £962 / week

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from £100 / night

(5) Excellent 

39

Farmhouse rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £76 / night

£436 - £471 / week

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from £76 / 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 £69 / night

£471 - £1539 / week

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from £69 / night

(15) Excellent 

23

Castelnuovo Berardenga holiday apartment rental

Province of Siena / Castelnuovo Berardenga

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“We enjoyed our holidays in this beautiful agriturismo” We have spent two weeks in Fernando Mattii's agriturismo. The site is very clean and very well maintained. Fernando Mattii was always helpful when we needed anything and he even brought us some wo  …see more

from £129 / night

£898 / week

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from £129 / night

(1) Excellent 

22

Province of Siena / Gaiole in Chianti

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £245 / night

£1710 - £2736 / week

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from £245 / night

27

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

 …see more

from £77 / night

£513 - £659 / week

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from £77 / night

(1) Excellent 

16

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 7 3 nights min

  • 1 bedroom
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Apt with terrace and large shared pool in an ancient borgo nestled in the countryside between Siena, San Gimignano and Volterra. It hosts 4 people comfortably, has 7 beds. Large living room with kitchen corner and a loft, master bedroom and bathroom with shower. It ha  …see more

from £59 / night

£359 - £509 / week

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from £59 / 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 £390 / night

£2338 - £4037 / week

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from £390 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

from £159 / night

£1112 - £1753 / week

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from £159 / night

(2) Excellent 

11

Siena holiday apartment rental

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
A spacious and luminous two roomed unit (55sqm) in Siena that can accommodate up to 4 guests; just 2 km outside the ancient walls of the historical centre of Siena. Private parking.  …see more

from £95 / night

£633 - £770 / week

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from £95 / night

18

Holiday villa with swimming pool in Gracciano

Montepulciano / Gracciano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Unique villa with swimming pool.  …see more

from £281 / night

£1966 - £2949 / week

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from £281 / night

20

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
This charming apartment 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 />Next to the garden and e  …see more

from £60 / night

£385 - £642 / week

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from £60 / night

(1) Excellent 

18

Province of Siena / Chiusdino

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool

 …see more

from £95 / night

£582 - £650 / week

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from £95 / night

(1) Very Good 

39

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £103 / night

£599 - £748 / week

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from £103 / night

(3) Very Good 

15

Siena holiday home rental

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The apartment is located just 5 minutes drive from the walls surrounding the old town (10 min by bus) and its location also allows you to quickly reach the surroundings of the Sienese countryside. Supermarket and shops nearby.<br />Being a one bedroom apartment of  …see more

from £65 / night

£428 / week

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from £65 / night

20

Holiday manor house rental

Province of Siena / Chiusi

8 21 7 nights min

  • 8 bedrooms
  • Sleeps 21
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool
This large country house, located in the hills between Lake Chiusi and Lake Trasimeno is an ideal property for a large family or a group of friends that which to spend their holidays together in the beautiful Tuscan countryside.This property is particular suitab  …see more

from £305 / night

£2129 - £3189 / week

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from £305 / night

24

Province of Siena / Sarteano

20 48 Min stay varies

  • 20 bedrooms
  • Sleeps 48
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

(9) Excellent 

52

Province of Siena / Montepulciano

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

 …see more

from £120 / night

£727 / week

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from £120 / night

16

Siena / Sant Andrea a Montecchio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£419 / week

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from £60 / night

(3) Very Good 

23

Holiday farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A unique and enchanting place” We have been going to Tuscany every summer for a while, and are used to renting houses in beautiful properties… We were not expecting to be surprised and overwelmed again by the beauty of a new place. However, Casanova (  …see more

from £257 / night

£1795 / week

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from £257 / 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 £107 / night

£624 - £949 / week

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from £107 / night

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
A cypress tree lined road will lead you to Villino Siena and it represents a perfect introduction to this amazing Tuscany villa located just 15 minutes walking from Piazza del Campo, the very heart of Siena. From its privileged hilltop position it enjoys spectacular vie  …see more

from £135 / night

£941 - £2137 / week

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from £135 / night

(1) Excellent 

14

Asciano / Crete Senesi

1 2 Min stay varies

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

 …see more

from £77 / night

£453 - £599 / week

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from £77 / night

(3) Very Good 

22

Holiday apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Ask about pets
“Great pool, very quiet in the day time & nice roomy accomodation” The apartment was spacious, comfortable and spotlessly clean. The pool was a lovely surprise, large and pleasant!! We wanted to go to a place where we were kids were unlikely and we ch  …see more

from £77 / night

£479 - £539 / week

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from £77 / night

(2) Excellent 

24

Holiday apartment with shared pool in Monticchiello

Pienza / Monticchiello

3 7 5 nights min

  • 3 bedrooms
  • Sleeps 7
  • 5 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Casa Oriolo is an elegant apartment with 3 bedrooms and it is part of a small complex with 3 apartments total sharing a pool. Here you can enjoy a sojourn in contact with nature in a protected and uncontaminated oasis.The owners have carefully furnished the prop  …see more

from £153 / night

£1069 - £1667 / week

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from £153 / 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 £52 / night

£300 - £419 / week

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from £52 / night

(3) Excellent 

24

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £30 / night

£174 - £342 / week

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from £30 / night

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Nr. San Gimignano, Siena Province, Tuscany, Italy Typical Tuscan Style Villa with Private Pool and Large Private garden. 12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive Grove Wonderful stone building situated in a peaceful position wit  …see more

from £137 / night

£1496 - £2565 / week

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from £137 / night

(2) Excellent 

21

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

3 5 4 nights min

  • 3 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 60 km
  • Suitable for children age 5+
  • Ask about pets
“Paradise in Radicondoli” We absolutely loved our stay at Casa Sulle Mura. Radicondoli is a beautiful town. We enjoyed the people there and especially enjoyed the evenings when people sit out and enjoy. The house is wonderful, clean and spacious.  …see more

from £137 / night

£684 / week

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from £137 / night

(4) Excellent 

24

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

6 17 7 nights min

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Self-catering Tuscany villa just 4 kms from San Gimignano. Private pool and garden for al fresco dining. Perfect centre for taking day trips to the cities and towns of Tuscany.  …see more

from £153 / night

£1069 - £2812 / week

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from £153 / 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 £52 / night

£300 - £513 / week

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from £52 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 £52 / night

£334 - £449 / week

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from £52 / 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 £121 / night

£847 - £1642 / week

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from £121 / night

13

Torrita di Siena holiday apartment rental

Province of Siena / Torrita di Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 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 £73 / night

£253 - £539 / week

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from £73 / night

(1) Very Good 

10

Holiday apartment in Siena

Province of Siena / Siena

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
There is a shopping area 500 meters away from the apartment: 3 supermarkets, shops, coffee, bar, bakery..  …see more

from £103 / night

£701 - £1026 / week

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from £103 / night