Province of Siena apartment or villa with a private pool area

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Province of Siena

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850 Holiday homes

Filters applied: Private pool (850)

(1) Excellent 

16

Province of Siena / Sarteano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £253 / night

£1345 - £1681 / week

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from £253 / 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 £278 / night

£1933 / week

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from £278 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £101 / night

£505 / week

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from £101 / night

22

Holiday apartment with swimming pool in Crete Senesi

Asciano / Crete Senesi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
t is a really relaxing apartment: the hall and the kitchen are characterized by green decorations and floral ornaments, whilst a gilt canopy-bed furnishes the big bedroom, where the ceiling is made of stones and beams. Also here the bathroom with shower is made of trave  …see more

from £101 / night

£706 / week

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from £101 / night

5

Home rental in Monteroni d'Arbia with swimming pool

Province of Siena / Monteroni d'Arbia

8 22 7 nights min

  • 8 bedrooms
  • Sleeps 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Monteroni d'Arbia: Villa Tinaio was originally the estate wine cellar. Because of its size, it can accomodate families or groups of friends up to 24 people who can enjoy moments of absolute relax, on the border of the private pool, surrounded by ancient trees.O  …see more

from £397 / night

£2774 - £4538 / week

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from £397 / night

32

Villa rental in Chianciano Terme with swimming pool

Province of Siena / Chianciano Terme

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
This compact, two-storey, converted Tuscan farmhouse has been extensively renovated, employing in its restoration solely products certified as ecologically friendly. It is set alongside a quiet country road, only 3 kms from the famous spa resort of Chianciano Terme. The  …see more

from £181 / night

£1261 - £2269 / week

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from £181 / night

100

Holiday villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

9 18 3 nights min

  • 9 bedrooms
  • Sleeps 18
  • 3 nights min
  • Swimming pool
  • Child friendly
This estate offers a main villa with space to accommodate up to 14 people, and an annex with space to sleep other 4 people  …see more

from £1200 / night

£8400 / week

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from £1200 / 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 £715 / night

£4538 - £6555 / week

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from £715 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa, with 4 bedrooms and 4 bathrooms can accomodate 8 people, so it is ideal for a large group of friends. Located in Tuscany Italy, this villa offers a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £550 / night

£3850 / week

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from £550 / 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 £127 / night

£883 - £1589 / week

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from £127 / night

(5) Excellent 

16

Farmhouse rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
TUSCANY (Montepulciano) PODERE SAN PIETRO, ancient country house recently restored, with 3 bathrooms, 4 bedrooms (max 10 sleepers), provided of private swimmingpool, fenced garden 3000 sq.m. Medium and small size pets are allowed.  …see more

from £169 / night

£1177 / week

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from £169 / night

24

Holiday villa rental

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly closed and the swimming pool, just below the house ground, has a lovely view over the val...  …see more

from £175 / night

£1222 - £2069 / week

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from £175 / 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 £505 / night

£2942 / week

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from £505 / 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 £316 / night

£2211 - £3244 / week

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from £316 / night

19

Holiday cottage with swimming pool in Sarteano

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cottage with swimming pool and small lake.  …see more

from £181 / night

£1261 - £1916 / week

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from £181 / night

(6) Excellent 

19

Holiday farmhouse in San Fabiano

Monteroni d'Arbia / San Fabiano

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The Count Filippo Fiorentini will host you in his residence near the village of Monteroni d'Arbia, at only 7 miles from Siena, in the gorgeous farm estate of San Fabiano, once owned by the Late Count Fiorentini, with a XII century castle, beautiful fields of sunflowers,  …see more

from £622 / night

£3614 - £4874 / week

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from £622 / 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 £358 / night

£2500 - £3992 / week

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from £358 / night

24

Villa rental in San Giovanni d'Asso with swimming pool

Province of Siena / San Giovanni d'Asso

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Centred around a pretty garden, Casa Vittorio is a notable, historic residence set over several levels and elegantly furnished. It is in a village location, just a short stroll from a restaurant, the castle and the truffl  …see more

from £713 / night

£4990 - £6090 / week

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from £713 / 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 £68 / night

£395 - £631 / week

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from £68 / night

(1) Excellent 

100

Holiday villa with swimming pool in Montepulciano

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Villa Albina is a sophisticated villa in Tuscany, located only 5km from Montepulciano. It has been carefully restored and features 7 large suites and bedrooms with private bathrooms, and lovely reception rooms, all set within an agricultural estate.  …see more

from £385 / night

£2690 - £5211 / week

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from £385 / night

(2) Excellent 

39

Holiday villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“A charming Tuscan farmhouse villa” We stayed here for a most enjoyable week in September 2016. It is all that the owner Giada describes and she is a charming and helpful host. The villa, a converted stone farmhouse, is located on the outskirts of Sien  …see more

from £110 / night

£740 - £2169 / week

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from £110 / night

(9) Excellent 

20

San Gimignano holiday villa rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about pets
  • Private garden
Naturally cool stone villa for 11 persons with large private pool & gardens in San Gimignano area. Divided into two apartments for 6 and 5 people.  …see more

from £180 / night

£1093 - £2017 / week

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from £180 / night

(3) Very Good 

24

Holiday farmhouse with swimming pool in Montepulciano

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 £229 / night

£1597 / week

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from £229 / 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 £177 / night

£1236 - £2853 / week

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from £177 / night

27

Montepulciano holiday villa rental

Province of Siena / Montepulciano

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Villa Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the suites and apartments are equipped with whirlpool bath, air conditioning, satellite TV, internet connection.The interior space in “arte pover  …see more

from £541 / night

£3782 - £6589 / week

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from £541 / 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 £241 / night

£1681 - £3278 / week

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from £241 / night

22

Province of Siena / San Gimignano

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Ask about pets

 …see more

from £183 / night

£1278 - £1517 / week

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from £183 / night

100

Holiday villa in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
This villa offers 8 bedrooms to accommodate up to two people each. They all have their own en-suite bathroom, and they share a beautiful dining room, two living areas, kitchen, covered patio and a fabulous garden with swimming pool.  …see more

from £458 / night

£3194 - £4622 / week

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from £458 / night

24

Monteriggioni holiday villa rental

Province of Siena / Monteriggioni

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
<span class="x_style25">Villa near Monteriggioni : Located in the heart of Tuscany, to the south of Florence, Villa Gianni is an attractive, small property, recently renovated and well furnished throughout. There are classic Tuscan views of vineyards and  …see more

from £229 / night

£1600 - £2510 / week

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from £229 / night

11

Torrita di Siena / Montefollonico

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £51 / night

£353 / week

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from £51 / night

18

Holiday apartment with swimming pool in Caprera

Siena / Caprera

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Recently renovated apartment over two floors, situated on top of the old riding stables, comfortably equipped and elegantly furnished with antique pieces of furniture.  …see more

from £227 / night

£787 - £874 / week

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from £227 / night

(1) Excellent 

16

Province of Siena / Chianciano Terme

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £59 / night

£412 / week

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from £59 / 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 £68 / night

£379 / week

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from £68 / night

100

Villa rental in Poggibonsi with swimming pool

Province of Siena / Poggibonsi

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Gorgeous country manor with swimming pool. Exquisitely decorated to a high standard and ideally located for guests to explore the wonderful region of Tuscany. Air conditioning and internet access are provided.  …see more

from £709 / night

£4959 - £6389 / week

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from £709 / night

43

Holiday villa rental

Province of Siena / Cetona

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Treat yourself to the ideal 2-bedroom home for your dream vacation in Tuscany! La Casella is a luxurious private villa set on a gentle hillside with lush gardens and private pool, outside dining, views and close enough to walk into town. This well furnished villa is set  …see more

from £202 / night

£1337 - £3101 / week

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from £202 / night

35

Holiday villa rental

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a se cluded parkland in the hills of Tuscany. The theme of the outdoors continues in the elegant drawing room, formerly a ballroom, whose vaulted ceiling and wal  …see more

from £571 / night

£3992 - £6093 / week

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from £571 / 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 £337 / night

£1345 - £2353 / week

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from £337 / night

22

Holiday villa rental

Colle di Val d'Elsa / Campiglia dei Foci

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Villa Nr. San Gimignano, Siena Province, Tuscany, ItalyTypical Tuscan Style Villa with Private Pool and Large Private garden.12.000 Square Metres Of Gardens, With Pine Trees, Monumental Oaks And Olive GroveWonderful stone building situated in a peaceful  …see more

from £157 / night

£1093 / week

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from £157 / night

(21) Excellent 

20

Holiday farmhouse with swimming pool in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
“Fabulous Tuscan villa experience!” Casa Bassa is a beautiful old Tuscan farmhouse and was the perfect central point for our stay in Tuscany. We were a party of 7, ranging in age from 16 to 63, and found the villa gave us ample space to gather togethe  …see more

from £250 / night

£2000 - £2750 / week

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from £250 / night

23

Province of Siena / Radicondoli

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 56 km
  • Swimming pool
  • Child friendly

 …see more

from £301 / night

£2101 / week

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from £301 / night