Province of Siena apartment or villa with a private pool area

Close

View larger map

Also consider

Europe Holidays
430742 properties
Italy Holidays
101490 properties
Tuscany Holidays
25170 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
450 properties
Villas Montepulciano
303 properties
Colle di Val d'Elsa
205 properties
Casole d'Elsa
202 properties
Castelnuovo Berardenga
200 properties
Poggibonsi
171 properties
Villas Castellina In Chianti
170 properties
Villas Montalcino
162 properties
Gaiole in Chianti
159 properties
Sinalunga
152 properties
Villas Pienza
146 properties
Rapolano Terme
144 properties
Asciano
113 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

867 Holiday homes

Filters applied: Private pool (867)

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

(6) Excellent 

21

Villa rental in Montisi with swimming pool

Province of Siena / Montisi

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A beautifully restored fully air-conditioned 16th century village house, filled with antiques. There are 4 bedroom/5 bath with stunning views, a garden overlooking the stunning Tuscan countryside, and a pool. Groceries, gelato and the best coffee within yards - and a fu  …see more

from £260 / night

£1650 - £2890 / week

Book View

from £260 / night

15

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £69 / night

£388 / week

Book View

from £69 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £108 / night

£755 / week

Book View

from £108 / night

Featured properties

110

Siena holiday villa rental

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena, the bus stop to the centre is 400 meters from the villa. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers. The villa has been completel  …see more

from £370 / night

£2587 - £3406 / week

Enquire View

from £370 / night

34

Province of Siena / Siena

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £173 / night

£1035 / week

Book View

from £173 / night

15

Casole d'Elsa holiday home rental

Province of Siena / Casole d'Elsa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 64 km
  • Swimming pool
  • Child friendly
Situated between San Gimignano and Siena, Villa San Giovanni is a beautiful renovated villa for an extended family or group of friends. The ancient medieval village of Casole d’Elsa is only 3 kilometres away and there are several interesting places within 35 Km. (  …see more

from £118 / night

£819 - £2199 / week

Book View

from £118 / night

20

Sarteano holiday manor house rental

Province of Siena / Sarteano

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful stone manor house with heated swimming pool and outdoor heated jacuzzi.  …see more

from £964 / night

£6742 - £16164 / week

Enquire View

from £964 / night

20

Villa rental in Castiglione D'Orcia with swimming pool

Castiglione D'Orcia / Gallina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Beautiful house with private pool in one of the most interesting area of Tuscany. It also perfect for trekking, jogging and mountain biking among the forests of Monte Amiata.  …see more

from £186 / night

£1294 - £2113 / week

Book View

from £186 / night

(1) Excellent 

23

Province of Siena / Sinalunga

9 31 Min stay varies

  • 9 bedrooms
  • Sleeps 31
  • Min stay varies
  • Nearest beach 98 km
  • Swimming pool
  • Child friendly

 …see more

from £647 / night

£4569 / week

Book View

from £647 / night

100

Larniano holiday villa rental

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this vacation villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £336 / night

£1940 - £3233 / week

Enquire View

from £336 / night

20

Farmhouse rental in Siena with swimming pool

Province of Siena / Siena

11 22 2 nights min

  • 11 bedrooms
  • Sleeps 22
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Casa Felice is an outstanding Tuscan farmhouse with 11 bedrooms and 11 bathrooms. It was recently renovated and brought back to its original splendour. Casa Felice is situated on a small road that leads to a wonderful medieval hamlet of Montebenichi.  …see more

from £1352 / night

£5406 / week

Enquire View

from £1352 / night

100

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

from £1170 / night

£8190 - £10345 / week

Enquire View

from £1170 / night

(11) Excellent 

41

Asciano / Crete Senesi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £61 / night

£423 - £733 / week

Book View

from £61 / night

(8) Excellent 

24

Rapolano Terme / Serre di Rapolano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

 …see more

from £82 / night

£561 / week

Book View

from £82 / night

25

Holiday villa with swimming pool in Sinalunga

Province of Siena / Sinalunga

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
it is the ideal place if you are looking to relax, private pool and beautiful view.  …see more

from £247 / night

£1725 - £3363 / week

Book View

from £247 / night

(2) Excellent 

40

Monticiano / Iesa Palazzo

6 9 1 night min

  • 6 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £156 / night

£1035 / week

Book View

from £156 / night

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from £518 / night

£3363 - £3707 / week

Enquire View

from £518 / night

(3) Excellent 

22

Holiday villa rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Centrum of city only 15 minutes by foot ! The villa was perfectly clean when we arrived. The kitchen is well equipped and fun to cook in.We highly recommend this property for those who are looking for a peaceful setting near all that Siena has to offer.  …see more

from £255 / night

£1078 - £2285 / week

Book View

from £255 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
“Well-located and roomy house” We were 10 adults and two children (three generations) spending one week at the house in May of 2014. We found the house very suitable (for five couples) since it had five large bedrooms. It was very convenient that each  …see more

from £234 / night

£1638 - £2932 / week

Book View

from £234 / 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

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

Book View

Pricing unknown

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £108 / night

£768 - £1897 / week

Book View

from £108 / night

(1) Excellent 

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Magda is a luxurious villa in San Gimignano, and is perfect for a large group of family or friends that appreciate tranquility, privacy, and beautiful natural surroundings.  …see more

from £733 / night

£4656 - £6725 / week

Enquire View

from £733 / night

100

Holiday villa with swimming pool in Province of Siena

Tuscany / Province of Siena

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 48 km
  • Swimming pool
  • Child friendly
Surrounded by natural woods and the most delightful quietness, this large villa sleeps up to 11 people and it offers an extended private garden with swimming pool, six bedrooms and exclusive amenities and comforts only 30km from Siena.  …see more

from £475 / night

£2199 - £3233 / week

Enquire View

from £475 / night

25

Siena holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £432 / night

£2069 - £3018 / week

Enquire View

from £432 / night

(9) Excellent 

24

Radicondoli holiday farmhouse rental

Province of Siena / Radicondoli

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“This was the perfect plpace for all of us” We were 12 people aged fron 20m to 65 years and this was ideal for us all. We felt really safe and it was so peaceful. There is plenty of land and also animals in the nearby fields which was great for the c  …see more

from £81 / night

£561 - £2544 / week

Enquire View

from £81 / night

46

Holiday castle rental

Province of Siena / Poggibonsi

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Enchanting Winery At the top of a hill with 309 hectares between wood, olive trees and wine yards is located this enchanting winery, with it’s amazing medioeval castle, the pool villa, the farmhouse and a real good Chianti wine production. This property is the ch  …see more

from £518 / night

£3621 - £4949 / week

Enquire View

from £518 / night

20

Siena holiday villa accommodation

Province of Siena / Siena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Villa Le Cantine di Cerreto is one of our best villas in Italy for rent. Immersed in the heart of the countryside with beautiful swimming pool, this spectacular villa can comfortably sleep up to 14 people and is ideal for your vacation rental in Italy.  …see more

from £2014 / night

£14098 / week

Enquire View

from £2014 / night

18

Holiday villa with swimming pool in Chiusi

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Monica is a typical Tuscan, farm house from 1700, recently converted to a prestigious holiday home,is surrounded by woods, cultivated fields, olive groves and vineyards  …see more

from £295 / night

£1811 - £2673 / week

Book View

from £295 / 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 £284 / night

£1983 - £2975 / week

Enquire View

from £284 / night

24

Holiday villa with swimming pool in Rapolano Terme

Province of Siena / Rapolano Terme

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Stunning villa in the Crete Senesi region  …see more

from £363 / night

£1509 - £2414 / week

Book View

from £363 / night

30

Montepulciano holiday watermill rental

Province of Siena / Montepulciano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 16 km
  • Swimming pool
  • Child friendly
Beutiful old structure located in one of the most unspoiled place in Tuscany. Peace and relax. Private garden with swimming pool , wifi, and inside parking. Villa for 6 people and another annex , for 4 people , is ideal for family or friends groups for a total of 10 p  …see more

from £147 / night

£966 - £1811 / week

Book View

from £147 / night

20

Holiday farmhouse with swimming pool in Palazzone

Province of Siena / Palazzone

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa in San Casciano dei Bagni with 7 bedrooms sleeps 13  …see more

from £785 / night

£5489 - £7982 / week

Enquire View

from £785 / night

(1) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The Casale is a very nice private villa, reachable through a dirt road easy to go also with a city car! The villa has a private swimming pool, outdoor BBQ and Jacuzzi, 5 bedrooms and 5 bathrooms (at least 10 people), it also has a big kitchen a big living room with fire  …see more

from £285 / night

£1983 / week

Book View

from £285 / night

(1) Excellent 

24

Holiday villa with swimming pool in Poggibonsi

Province of Siena / Poggibonsi

7 18 7 nights min

  • 7 bedrooms
  • Sleeps 18
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa with pool in Chianti is located near the town of Poggibonsi, surrounded by the gently rolling hills of this beautiful region. The accommodation is on two floors and can comfortably accommodate up to 18 people. Accommodation, 400 sqm : GROUND FLOOR  …see more

from £238 / night

£1664 - £4009 / week

Book View

from £238 / night

17

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Small farmhouse with swimming pool which can be covered.  …see more

from £124 / night

£863 - £1483 / week

Enquire View

from £124 / night

(1) Excellent 

32

Sinalunga / Rigaiolo

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

 …see more

from £182 / night

£1268 - £2927 / week

Book View

from £182 / night

41

Pienza / Monticchiello

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £151 / night

£1035 - £1207 / week

Book View

from £151 / night

20

Province of Siena / Chiusdino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £370 / night

£2587 - £3276 / week

Book View

from £370 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a lovely villa set in Tuscany Italy. It has 2 bedrooms and 2 bathrooms, and it is perfect for those who are looking for a unique experience. This property features: a swimming Pool, air Conditioning .  …see more

from £168 / night

£983 - £1639 / week

Enquire View

from £168 / night