Apartments and villas with a garden in Province of Siena

Close

View larger map

Also consider

Europe Holidays
430742 properties
Italy Holidays
102113 properties
Tuscany Holidays
25513 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas San Gimignano
497 properties
Villas Siena
458 properties
Villas Montepulciano
304 properties
Colle di Val d'Elsa
206 properties
Castelnuovo Berardenga
204 properties
Casole d'Elsa
203 properties
Poggibonsi
176 properties
Villas Castellina In Chianti
170 properties
Villas Montalcino
163 properties
Gaiole in Chianti
159 properties
Villas Pienza
152 properties
Sinalunga
152 properties
Rapolano Terme
144 properties
Asciano
126 properties

Province of Siena

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

2,405 Holiday homes

Filters applied: Garden (2,526)

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

(2) Excellent 

17

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful holiday resort near Montepulciano and Pienza  …see more

from £95 / night

£544 - £996 / week

Book View

from £95 / 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 £52 / night

£363 - £690 / week

Book View

from £52 / 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 £138 / night

£949 / week

Book View

from £138 / night

Featured properties

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 £307 / night

£2147 - £3216 / week

Enquire View

from £307 / night

26

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 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 £41 / night

£281 - £535 / week

Book View

from £41 / night

(3) Excellent 

18

Montalcino holiday studio rental

Province of Siena / Montalcino

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
All the charm and comfort for an artistic stay in the heart of Tuscany. Montalcino has remained quite untouched and therefore has kept it's charming atmosphere. Moreover, if you love food and wine, especially Brunello, you cannot go wrong around here, come and enjo  …see more

Pricing unknown

Book View

Pricing unknown

(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 £468 / night

£3276 - £4225 / week

Book View

from £468 / night

25

Province of Siena / San Gimignano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£485 - £793 / week

Book View

from £77 / night

(2) Excellent 

16

Radicondoli holiday apartment rental

Province of Siena / Radicondoli

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Wonderful peaceful stay in the heart of the Tuscan countryside” The apartment at Radicondoli was wonderful. Just perfect for our requirements. It had everything you could need (except an ironing board). It was exceptionally clean, had an amazing showe  …see more

Pricing unknown

Book View

Pricing unknown

(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 £44 / night

£302 / week

Book View

from £44 / night

(2) Very Good 

22

Villa rental in Montepulciano

Province of Siena / Montepulciano

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 180 km
  • Child friendly
  • Pet friendly
La Villa è situata poco fuori le mura, in prossimità del Tempio di San Biagio. Internamente si trovano due camere da letto, due bagni, uno spazioso e luminoso salone con divano letto, cucina e sala da pranzo. Esternamente gode di un meraviglioso panorama  …see more

from £87 / night

£518 / week

Book View

from £87 / night

49

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
Apartment in old Monastery, very small village in Tuscan country.15 Kms to San Gimignano and Volterra, Colle di Val d'Elsa.Monteriggioni and Siena are at less than 30 minutes.Florence and Pisa are at about 1 hour.Cooking classes available in a near farm holiday  …see more

from £52 / night

£302 - £423 / week

Book View

from £52 / night

31

Asciano holiday villa let

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a spectacular villa, immaculately furnished and presented in a wonderful part of Italy. The owners have imported furniture from around the world to create a unique setting for guests to enjoy their stay. Complete with private pool and beautiful gardens, it'  …see more

from £302 / night

£1682 - £3621 / week

Book View

from £302 / night

(15) Very Good 

97

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
“Wonderful place, we'll come back!” Everything was first class: the rooms, the pool, breakfast, the countryside. We enjoyed a walk in the countryside and had an archery session with a very patient instructor. Staff is very friendly and helpful.  …see more

from £518 / night

£3018 / week

Book View

from £518 / night

(2) Excellent 

21

Holiday farmhouse with shared pool in Radicondoli

Province of Siena / Radicondoli

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Beautiful house, amazing scenery!” We stayed here for two weeks and loved the place! The view is breathtaking! Bed was very comfortable. In the villa we found everything for cooking, towels. The location is very convenient for visiting little towns ar  …see more

from £44 / night

£302 - £604 / week

Book View

from £44 / 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 £61 / night

£423 / week

Book View

from £61 / 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 £104 / night

£604 - £755 / week

Book View

from £104 / 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 £190 / night

£707 - £1121 / week

Book View

from £190 / night

35

Holiday villa with swimming pool in Castelmuzio

Province of Siena / Castelmuzio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
When Eric and Kathy decided they wanted to settle in Tuscany and provide people with the sort of holidays they themselves had always dreamed of - but had rarely been able to find - they knew they had found the ideal property in Castelmuzio for many reasons, amongst whic  …see more

from £432 / night

£3018 - £4095 / week

Enquire View

from £432 / night

52

Holiday villa rental

Poggibonsi / Staggia Senese

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence. Villa Senese is an holiday villa in Tuscany, located in a vantage position on a hill above the old town  …see more

from £518 / night

£3621 - £4828 / week

Enquire View

from £518 / night

19

Holiday farmhouse with shared pool in Sarteano

Province of Siena / Sarteano

4 5 Min stay varies

  • 4 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Apartment in Sarteano with 3 bedrooms sleeps 5  …see more

from £133 / night

£776 - £1099 / week

Enquire View

from £133 / night

(11) Excellent 

27

Holiday cottage with swimming pool, golf nearby in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“A lovely villa in beautiful surroundings.” We have recently returned from our first holiday in Tuscany with our two young sons and all agree that we will return to this area again. The villa although a short drive into Casole was situated amongst oli  …see more

from £116 / night

£690 - £992 / week

Enquire View

from £116 / 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 £65 / night

£453 / week

Book View

from £65 / 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

£302 - £518 / week

Book View

from £52 / night

4

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool

 …see more

from £62 / night

£432 / week

Book View

from £62 / 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

Enquire View

from £300 / 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 £173 / night

£1207 - £1811 / week

Book View

from £173 / night

(1) Excellent 

24

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Italian village rental - This charming historic residence with private pool is located in the village of San Giovanni d'Asso, and it is just a short stroll from your door to the castle, the truffle museum and a nice  …see more

from £250 / night

£1750 - £2460 / week

Enquire View

from £250 / night

20

Chiusi holiday villa rental

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa with lovely swimming pool set in a nature reserve, near the lake, ideal for bird watching and cycling.  …see more

from £146 / night

£1018 - £2578 / week

Enquire View

from £146 / night

(8) Excellent 

31

Province of Siena / Siena

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £104 / night

£725 / week

Book View

from £104 / 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 £104 / night

£707 - £1035 / week

Book View

from £104 / night

(1) Excellent 

27

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
holiday lodging near Pienza. Torrita di Siena accommodation  …see more

from £51 / night

£354 - £660 / week

Book View

from £51 / night

26

Villa rental in Sant'Albino with swimming pool

Montepulciano / Sant'Albino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The property is situated in the heart a working farm with breathtaking views over the valley where Vino Nobile di Montepulciano is produced. The villa ha  …see more

from £259 / night

£1811 - £3104 / week

Enquire View

from £259 / night

27

Radicondoli holiday home rental

Province of Siena / Radicondoli

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
This typical stone house is situated in a panoramic position about 200 m. from Radicondoli, a characteristic and attractive mediaeval village (population 1.000) situated in a hilly position about 45 km from Siena. Guests can therefore avail of all the facilities availa  …see more

from £95 / night

£561 - £1294 / week

Enquire View

from £95 / night

(4) Excellent 

42

Province of Siena / Siena

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £87 / night

£432 / week

Book View

from £87 / 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 £74 / night

£255 - £544 / week

Book View

from £74 / night

(1) Excellent 

15

Holiday apartment with swimming pool in Radicofani

Province of Siena / Radicofani

1 4 Min stay varies

  • 1 bedroom
  • 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 period furniture, fireplace, Sky TV, independent heating external, private space. Park, scenic swimming pool.  …see more

from £69 / night

£406 - £647 / week

Book View

from £69 / night

(1) Average 

28

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Private garden

 …see more

from £104 / night

£604 - £776 / week

Book View

from £104 / night

(1) Excellent 

24

Holiday villa with swimming pool in Montalcinello

Chiusdino / Montalcinello

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
Luxury Villa with pool near San Galgano / 8 bedrooms - 9 bathrooms  …see more

from £339 / night

£2371 - £3880 / week

Enquire View

from £339 / night

25

Holiday apartment with shared pool in Torrita di Siena

Province of Siena / Torrita di Siena

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 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 £42 / night

£294 - £587 / week

Book View

from £42 / night