Province of Siena apartment or villa with a private pool area

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938 Holiday homes

Filters applied: Private pool (938)

(42) Excellent 

35

Beautiful Private Villa, pool, hot tub,wi-fi,Siena - Siena villa sleeps 12

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
JUST RELAX...... YOUR VACATION IN TUSCANY BEGINS NOW!!!! What we want is to make this holiday as pleasant and relaxing as possible, so we want to make available to you our Villa, that for a time, long or short it might be, will be YOUR HOME in Tuscany. A HOLIDAY WITHOUT  …see more

from £243 / night

£1696 - £4348 / week

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from £243 / 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 £70 / night

£392 / week

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from £70 / night

(4) Excellent 

20

Classic Tuscan farmhouse surounded by brethtaking - Radicofani farmhouse sleeps 7

Province of Siena / Radicofani

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
L'Olivo (sleeps 5+2), 86 sq.m, is made up of a living room with fireplace and sofa-bed, kitchenette, a double bedroom, a triple bedroom (one double bed and one single bed, or three single beds), two bathrooms with a shower, hairdryer.It is part of Podere Pietreta w  …see more

from £131 / night

£566 - £783 / week

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from £131 / night

14

Castelnuovo Berardenga / Montaperti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £119 / night

£827 / week

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from £119 / night

(3) Very Good 

21

Sovicille / Torri

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £79 / night

£479 / week

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from £79 / night

(2) Very Good 

20

Lovely hillside cottage in the Province of Siena w - Belforte cottage sleeps 6

Radicondoli / Belforte

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
In the picturesque setting of the "Metallifere" hills, west from Siena, is located this characteristic stone built house, recently renovated in keeping with the traditional style and character, with wood beams and terra cotta floors, furnished in a comfortable, rustic s  …see more

from £53 / night

£366 - £435 / week

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from £53 / night

(1) Excellent 

100

Albino - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
ExteriorVilla Albino is a sophisticated and at the same time relaxed villa for 14 people in Tuscany. It is conveniently located just 5km away from Montepulciano, a privileged position to explore all of central Italy. It is within easy reach of Pienza, Montalcino, Bagno,  …see more

from £348 / night

£2435 - £5392 / week

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from £348 / night

(15) Very Good 

97

7 bedroom Tuscan farmhouse near rennaissance town of Montepulciano, features include jacuzzi, private garden and pool - Montepulciano farmhouse sleeps 16

Province of Siena / Montepulciano

7 16 1 night min

  • 7 bedrooms
  • Sleeps 16
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The watermill “Il Molinaccio”, near the renaissance town of Montepulciano, was already present in the old maps of the Granduchy of Tuscany . The original building, duly and let me say passionately restored, now reopens as a luxury country house where the guests may  …see more

from £522 / night

£3044 / week

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from £522 / night

25

Province of Siena / Gallina

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £140 / night

£974 / week

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from £140 / night

24

Orcia Valley country house - Castiglione D'Orcia villa sleeps 21

Province of Siena / Castiglione D'Orcia

8 21 Min stay varies

  • 8 bedrooms
  • Sleeps 21
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This beautiful holiday home in the Val d'Orcia, surrounded by gently rolling hills, is near Castiglione d'Orcia (12km), just a few kilometres from the famous spa waters at Bagno Vignoni (10km) and Bagni San Filippo (7km). Surrounded by peace and quiet this lovely farmho  …see more

from £435 / night

£1653 - £3627 / week

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from £435 / night

33

Country House Maramai in the lush Chiana valley - Gracciano villa sleeps 9

Montepulciano / Gracciano

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Maramai lies on the Gracciano estate, one of the most renowned producers of the Vino Nobile di Montepulciano, one hour south of Florence in the lush Chiana valley. The restored farmhouse with pool with 7 to 9 beds is the perfect base to explore the surrounding Tuscany l  …see more

from £295 / night

£2061 - £3470 / week

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from £295 / night

18

BELLAVALLE - Siena villa sleeps 10

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
An eighteenth century Tuscan farmhouse in a delightful little valley along the historic Via Francigena, surrounded by 14 hectares of privately owned vines, olive trees and woods that ensure utter privacy and tranquillity – this is Bellavalle, just 3.5 kilometres from  …see more

from £858 / night

£3566 - £6000 / week

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from £858 / night

100

Fiordaliso - San Giovanni d'Asso villa sleeps 10

Province of Siena / San Giovanni d'Asso

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Exterior This enchanting villa is located in the heart of Tuscany, near Pienza. It is situated in the middle of an old olive grove and has one of the most stunning views in all of Tuscany. Besides the lovely city of Pienza, you’ll also be near Montepulciano, Cor  …see more

from £435 / night

£3044 - £4131 / week

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from £435 / night

(8) Excellent 

20

Three bedroom apartment in stunning villa - San Gimignano villa sleeps 6

Province of Siena / San Gimignano

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Osservatorio is a stunning villa for up to 11guests divided into two independent units. Orione apartment for up to 6 guests.The property is extraordinarily cool and pleasant throughout the summer, thanks to its location on a higher altitude (about 500 AMSL) and the beau  …see more

from £187 / night

£1305 - £1479 / week

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from £187 / 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 £109 / night

£774 - £1722 / week

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from £109 / night

26

Charming Villa in the Crete Senesi - San Giovanni d'Asso villa sleeps 8

Province of Siena / San Giovanni d'Asso

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This charming old hamlet is located at 5 km from San Giovanni d'Asso, in the heart of the Crete Senesi, at just 13 km from Pienza and 16 km from Montalcino. The estate belonged for six hundred years to the notorious Piccolomini family, a protagonist of Italian Ren  …see more

from £353 / night

£4596 / week

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from £353 / night

19

APARTMENT VIOLA 2203 - Casaglia apartment sleeps 3

San Gimignano / Casaglia

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Located on the first floor of the main villa, Viola is a large apartment comprised of one double bedroom (with king size bed and a bed for a child), a bathroom (with shower stall), kitchen and dining room / living room.It is a very quite and intimate apartment, with a p  …see more

from £92 / night

£600 - £750 / week

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from £92 / night

24

Luxury villa near Pienza - Pienza villa sleeps 13

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This magnificent holiday villa with swimming pool (18mx4, open Apr-Oct) sits on one of the knolls at the foot of Pienza (3km) with a breathtaking 360 degree view over the Val d'Orcia countryside. The villa is a tastefully restored stone farmhouse, beautifully furnished  …see more

from £317 / night

£2218 - £5957 / week

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from £317 / 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 £249 / night

£1740 - £2783 / week

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from £249 / night

59

Province of Siena / Chianciano Terme

6 21 Min stay varies

  • 6 bedrooms
  • Sleeps 21
  • Min stay varies
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

 …see more

from £392 / night

£2740 / week

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from £392 / night

12

Agriturismo Terrarossa 4px - Valiano apartment sleeps 4

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano. It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nobile  …see more

from £131 / night

£522 - £653 / week

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from £131 / night

(15) Excellent 

23

Podere Scopicciolo - Casole d'Elsa villa sleeps 12

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 £895 / night

£6261 - £9131 / week

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from £895 / night

16

Villa Fontana - Castellina In Chianti villa sleeps 8

Province of Siena / Castellina In Chianti

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway.The garden spaces and external paved terraces are all abundantly  …see more

from £545 / night

£2180 - £3894 / week

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from £545 / night

100

San Gimignano 80249 - Larniano villa sleeps 10

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Characteristic stone villa created from a carefully-renovated barn, just 5 km from the captivating medieval village of San Gimignano, and just 6 km from the charming town of Certaldo. The property is independent and offers a large, completely enclosed garden (2000 m2) a  …see more

from £342 / night

£1976 - £3294 / week

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from £342 / night

23

Villa Leccio - Monticiano villa sleeps 9

Province of Siena / Monticiano

9 9 Min stay varies

  • 9 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Leccio is a world apart set in a charming and peaceful place where guests can truly relax and rediscover a calmer pace of life, away from the city. The villa is nesteled in the beautiful unspoiled widerness of a natural reserve. It is close to Siena and to San Gal  …see more

Pricing unknown

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Pricing unknown

31

Il Poggiarone Montepulciano - Montepulciano villa sleeps 14

Province of Siena / Montepulciano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden
Il Poggiarone is a splendid farmhouse with typical Tuscan architectural features, set in an extremely panoramic position and the ideal destination for those who are looking for a holiday which is a mix of art, history and nature. The beautiful villa is near the owner's  …see more

from £164 / night

£1148 - £2122 / week

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from £164 / night

24

10 bedroom Tuscany villa with private pool - Monteroni d'Arbia villa sleeps 20

Province of Siena / Monteroni d'Arbia

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This is a large 10 bedroom villa set over three floors and located at the end of a cypress lined avenue within secluded parkland in the hills of Tuscany. Built in the eighteenth century, the villa is furnished in a style in keeping with the era and has many original his  …see more

from £696 / night

£4783 - £6522 / week

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from £696 / night

24

Biancaserena - Cetona villa sleeps 9

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
Siena countryside family villa – Conveniently located south of Siena, Biancaserena is a modern villa surrounded by the typical, idyllic Tuscan landscape of vine-clad hills, extensive olive groves and cypress trees, dotted with picturesque hilltop villages such as Ceto  …see more

from £247 / night

£1725 - £3450 / week

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from £247 / night

100

Petit Verdot - Montepulciano villa sleeps 10

Province of Siena / Montepulciano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
ExteriorsOriginally built in the 17th century rural Tuscany, the Villa has been restored without altering its original architecture. Siena's typical ocher colors dominate the villa's stone walls and diffuse a welcoming glow on the light blue of the infinity pool. All ar  …see more

from £435 / night

£3044 - £3392 / week

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from £435 / night

(29) Excellent 

26

Fonte Aulente Montalcino - Val d'Orcia farmhouse sleeps 5

Montalcino / Val d'Orcia

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own ent  …see more

from £118 / night

£822 / week

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from £118 / night

(2) Excellent 

41

Province of Siena / Cetona

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 28 km
  • Swimming pool

 …see more

from £305 / night

£2131 / week

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from £305 / night

(14) Excellent 

24

Renovated 5 bedroom villa surrounded by Tuscan vineyards, fetures private pool, log fire and terrace - San Gimignano villa sleeps 12

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
The completely renovated property occupies a panoramic position within an estate of olive groves and vineyards, boasting an entrancing view of the famous towers of San Gimignano 4 km away. The characteristic architecture enables guests to experience a specifically Tusc  …see more

from £348 / night

£1566 - £2087 / week

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from £348 / night

(1) Excellent 

12

Province of Siena / Cetona

5 6 Min stay varies

  • 5 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 28 km
  • Swimming pool
  • Child friendly

 …see more

from £305 / night

£2131 / week

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from £305 / night

20

Villa Serravalle - Buonconvento house sleeps 10

Province of Siena / Buonconvento

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautifully restored 14th century farmhouse sits within a farming estate on a hilltop with magnificent views over the soft hills of the Arbia river valley. The owners have personally directed the restoration of the house and produced an impeccably tasteful but mode  …see more

from £964 / night

£3856 - £6230 / week

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from £964 / night

100

Farnetella 56708 - Sinalunga villa sleeps 7

Province of Siena / Sinalunga

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Old stone farmhouse restored with the 1700 conservative policy that has left intact the charm and beauty of the past. Located between the Val d'Orcia and the hills of Chianti, the farmhouse is divided on two floors: on the first floor is accessed by an ancient ston  …see more

from £241 / night

£1625 - £1933 / week

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from £241 / night

(4) Excellent 

19

Il Giardino - San Giovanni d'Asso villa sleeps 8

Province of Siena / San Giovanni d'Asso

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
+Dream house in idyllic setting beautifully restored by the Anglo-Irish artist/owner. Of a pleasing architecture of warm sienese bricks, in perfect conditions, the house offers an atmosphere of extreme comfort and relaxation. Pool decoratively immersed in herbs, rose  …see more

from £215 / night

£1500 - £7950 / week

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from £215 / night

100

Castellina In Chianti 46441 - Castellina In Chianti villa sleeps 16

Province of Siena / Castellina In Chianti

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £395 / night

£2763 - £2771 / week

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from £395 / night

20

Primrose Villa (V039) - Chiusi villa sleeps 8

Province of Siena / Chiusi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
At Chiusi lake, this beautiful villa is a peaceful and cosy place for a holiday in close contact with nature. The restoration work, using environmentally friendly techniques paid attention to every detail, making the interiors light and comfortable. Extremely well furni  …see more

from £147 / night

£1027 - £2600 / week

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from £147 / night

(10) Excellent 

24

Romantic Tuscan cottage, sleeps four, total priva - Casole d'Elsa cottage sleeps 6

Province of Siena / Casole d'Elsa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Casa Daniela' is a well farm into a romantic country cottage. The house ( Total independent ) - in the surroundings of Casole d'Elsa, a medieval village with Etruscan origins – is located on a hill surrounded by a large olive grove and a pretty garden. Inside the ma  …see more

from £118 / night

£696 - £914 / week

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from £118 / night

21

Cosy apartment in villa, Siena, pool and garden - Val d'Orcia apartment sleeps 9

Montalcino / Val d'Orcia

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
One of three unique and charming apartments in a XVI century villa situated in the wonderful senese countryside a few km's from Montalcino, in the natural park of the Val d' Orcia, a precious architectural and natural context.Here you will feel embraced by the  …see more

from £199 / night

£1392 - £1614 / week

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from £199 / night

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