Province of Siena apartment or villa with a private pool area

Close

View larger map

Also consider

Europe Holidays
419302 properties
Italy Holidays
101462 properties
Tuscany Holidays
24841 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 Siena
481 properties
Villas San Gimignano
473 properties
Villas Montepulciano
288 properties
Castelnuovo Berardenga
208 properties
Colle di Val d'Elsa
184 properties
Casole d'Elsa
176 properties
Gaiole in Chianti
168 properties
Poggibonsi
164 properties
Villas Montalcino
155 properties
Villas Castellina In Chianti
155 properties
Villas Pienza
148 properties
Sinalunga
142 properties
Rapolano Terme
130 properties
Asciano
119 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

859 Holiday homes

Filters applied: Private pool (859)

(1) Excellent 

16

Villa rental in Chiusi with swimming pool

Province of Siena / Chiusi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Baiocco is a typical Tuscan home, newly built in the traditional farmhouse style, perfectly blending with the Italian countryside. Surrounded by a well kept park, for your private use only, it offers all the peace and tranquility that you look for during your holid  …see more

from £61 / night

£424 - £1314 / week

Book View

from £61 / night

(5) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi  …see more

from £60 / night

£382 - £471 / week

Book View

from £60 / 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

Enquire View

from £152 / 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 £297 / night

£1314 - £2119 / week

Enquire View

from £297 / 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 £260 / night

£1820 - £2560 / week

Enquire View

from £260 / night

(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 £460 / night

£3221 - £4153 / week

Book View

from £460 / night

24

Celle sul Rigo holiday villa rental

San Casciano dei Bagni / Celle sul Rigo

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
The farmhouse is located near Radicofani, under the UNESCO Patrimony (being a part of the Val d'Orcia) 4.5 km from the town centre along the old dirt Francigena Road. The ancient house, restructured with a rustic style, is part of a farm with 96 hectars of cu...  …see more

from £185 / night

£1289 - £2312 / week

Enquire View

from £185 / 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 PeacefullThe 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

Book View

from £119 / night

(43) Excellent 

39

Holiday villa in Siena

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The  …see more

from £237 / night

£1242 - £4238 / week

Book View

from £237 / night

(1) Average 

4

Province of Siena / Sinalunga

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool

 …see more

from £119 / night

£763 / week

Book View

from £119 / night

100

Holiday villa rental

Sinalunga / Guazzino

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
This villa offers 4 bedrooms and a suite in the main body and four neighbouring cottages with one or two bedrooms, kitchen or kitchenette.  …see more

from £594 / night

£4153 - £7890 / week

Enquire View

from £594 / 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

Book View

from £339 / night

100

San Giovanni d'Asso holiday villa rental

Province of Siena / San Giovanni d'Asso

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa for anyone looking for a relaxing and peaceful getaway in Tuscany.  …see more

from £364 / night

£2543 - £3390 / week

Enquire View

from £364 / night

(4) Excellent 

21

Holiday apartment in Val d'Orcia

Montalcino / Val d'Orcia

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“Fantastic experience in a gorgeous setting that exceeded all expectations.” My wife and I spent a week here with our three teenage boys and all of us loved the place. The reality of the home is even better than the photos and we hated to leave. Hosts  …see more

from £231 / night

£1611 - £1865 / week

Book View

from £231 / night

100

Holiday villa with swimming pool in Pienza

Province of Siena / Pienza

8 14 7 nights min

  • 8 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people.  …see more

from £727 / night

£5085 - £8475 / week

Enquire View

from £727 / night

(6) Very Good 

43

Gaiole in Chianti holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £46 / night

£265 - £594 / week

Book View

from £46 / night

18

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This stone house was originally inhabited by a large family of farmers who worked for the monks of the nearby Abbey of Spineto. Excellent furnishing.Ground floor: large kitchen, with wood fired oven, opening directly onto the garden, spacious dining room, study  …see more

from £385 / night

£2695 - £3534 / week

Enquire View

from £385 / night

100

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
At Villa Valpoliziana, which has been described as a ´paradise on earth´ you will rediscover how to relax and get in touch with nature surrounded by wonderful opportunities to discover the amazing Tuscan culture and wonderful towns such as Montepulci  …see more

from £467 / night

£2119 - £3178 / week

Enquire View

from £467 / 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 £509 / night

£3306 - £3645 / week

Enquire View

from £509 / night

(2) Excellent 

24

Holiday villa with swimming pool in Siena

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa in Siena with SPA room and swimming pool at exclusive use.  …see more

from £231 / night

£1611 - £3389 / week

Book View

from £231 / 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 £97 / night

£678 - £1060 / week

Book View

from £97 / night

20

Farmhouse rental in Radicofani with swimming pool

Province of Siena / Radicofani

11 26 7 nights min

  • 11 bedrooms
  • Sleeps 26
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Hunting lodge of the second half of the XVIII century, surrounded by a park of oaks and cypress trees. Beautiful infinity swimming pool (6x12 m).  …see more

from £669 / night

£4678 - £5458 / week

Enquire View

from £669 / night

20

Holiday villa rental

Province of Siena / Radicofani

1 12 7 nights min

  • 1 bedroom
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This was an old monastery during the first half of the sixteenth century and went on to become a summer residence for the friars of Monte Oliveto Maggiore. It enjoys beautiful views across a valley. Old farmhouse, well restored, divided into three apartments.  …see more

from £177 / night

£1238 - £1517 / week

Enquire View

from £177 / night

(1) Excellent 

27

Holiday barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Restored Barn, description: this ground floor flat has an entrance with three large glass doors. The main living area has an open fireplace and is divided into a sitting room and a large kitchen. Dining table, wicker armchairs. Sofa bed for one person. From this room th  …see more

from £81 / night

£441 - £856 / week

Book View

from £81 / night

(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 £106 / night

£755 - £1678 / week

Book View

from £106 / night

32

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 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 £128 / night

£890 - £1602 / week

Book View

from £128 / 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 £721 / night

£4577 - £6611 / week

Enquire View

from £721 / night

19

Holiday cottage with swimming pool in Cetona

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Pretty, restored cottage with swimming pool and bowling alley.  …see more

from £319 / night

£2229 - £3272 / week

Enquire View

from £319 / night

25

Holiday villa with swimming pool in Rigomagno

Sinalunga / Rigomagno

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
On demand services: Tranfer and Taxi serviceWine and Olive Oil TastingsCooking LessonsDinners  …see more

from £212 / night

£1526 - £1992 / week

Book View

from £212 / night

(15) Excellent 

23

Casole d'Elsa holiday villa rental

Province of Siena / Casole d'Elsa

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Villa Podere Scopicciolo is located about 30 miles from Florence. It is 900 ft above sea level in the heart of Tuscany surruonded by cultivated farm land and well preserved forests. It is fully immersed in the countryside enjoying peace and tranquillity, yet convenientl  …see more

from £908 / night

£6356 - £8899 / week

Enquire View

from £908 / night

20

Holiday villa in San Gusme

Castelnuovo Berardenga / San Gusme

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

from £107 / night

£746 - £1194 / week

Book View

from £107 / night

(30) Excellent 

26

Holiday farmhouse with swimming pool in Val d'Orcia

Montalcino / Val d'Orcia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
“Perfect cottage for two” Loved everything about our stay here. Alexandra was so helpful, with directions, shopping, restaurants and her love of the wine industry. She met us on the road when we got lost. Lives next door but the property is so big  …see more

from £115 / night

£801 / week

Book View

from £115 / 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 £255 / night

£170 - £1780 / week

Book View

from £255 / night

(16) Excellent 

22

Casole d'Elsa holiday cottage rental

Casole d'Elsa / Monteguidi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
“Everything we wanted: excellent villa with lovely pool, beautiful countryside views and welcoming owners.” La Casa Dei Nonni was above and beyond our expectations. The location within the Tuscan hillside village of Monteguidi was easy to find from the  …see more

from £128 / night

£763 - £1145 / week

Enquire View

from £128 / night

100

Montalcino holiday villa rental

Province of Siena / Montalcino

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a stunning villa set in Tuscany Italy. It has 4 bedrooms and 3 bathrooms, and it is ideal for those who are looking for a memorable experience. This property features: a swimming Pool, air Conditioning .  …see more

from £237 / night

£1656 - £2718 / week

Enquire View

from £237 / 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 £158 / night

£1102 / week

Book View

from £158 / 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 £183 / night

£1272 - £2077 / week

Book View

from £183 / night

20

Villa rental in Pienza with swimming pool

Province of Siena / Pienza

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a farm of 150 hectares producing excellent extra virgin olive oil, the farmhouse is set on a kind of natural terrace overlooking the lovely valley below.  …see more

from £480 / night

£3356 - £3899 / week

Enquire View

from £480 / night

20

Province of Siena / Chiusdino

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

 …see more

from £364 / night

£2543 - £3221 / week

Book View

from £364 / 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 £205 / night

£1433 - £1721 / week

Enquire View

from £205 / night