Villas with a pool Province of Siena | Apartments to rent with swimming facilities

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2,716 Holiday homes

Filters applied: Swimming pool (2,718)

12

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £68 / night

£432 - £669 / week

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from £68 / night

(7) Excellent 

15

Holiday farmhouse apartment rental in Tuscany, property features beautiful garden and private fishing lake - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dining room/k  …see more

from £61 / night

£414 - £785 / week

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from £61 / night

(1) Excellent 

9

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £69 / night

£414 - £638 / week

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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 £109 / night

£761 / week

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from £109 / night

18

Villa Monica - Chiusi villa sleeps 12

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The farmhouse was inhabited by a family of Umbrian farmers whose main occupation was cultivating their land, picking up its hard-earned fruits.The house is now surrounded by a garden with oak-trees, mulberry-trees, laurels, maples and lime-treesOn the inside walls, the  …see more

from £298 / night

£1827 - £2696 / week

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from £298 / night

19

Forsythia Cottage (V041) - Sarteano cottage sleeps 8

Province of Siena / Sarteano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Typical country house, well restructured, Mount Amiata dominates the unique landscape surrounding this property. From the interiors which are refined but cosy, you understand the owners' passion. Very well furnished.On the first floor there is a living room with fi  …see more

from £185 / night

£1294 - £1569 / week

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from £185 / night

24

casole country house pettirosso - Casole d'Elsa apartment sleeps 8

Province of Siena / Casole d'Elsa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Large apartment of 105 sqm on the second floor of the farmhouse which consists of an entrance, a fully equipped kitchen, a large sitting room with double divan bed and dining area, a small storeroom, a double bedroom with built-in wardrobe and a bathroom fitted with sho  …see more

from £114 / night

£696 - £1827 / week

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from £114 / night

(5) Very Good 

23

Spacious Chianti apartment with pool access, terrace and outdoor dining area - Gaiole in Chianti apartment sleeps 6

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village  …see more

from £150 / night

£600 - £850 / week

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from £150 / night

(4) Excellent 

33

Province of Siena / Murlo

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £69 / night

£475 - £561 / week

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from £69 / night

(16) Excellent 

22

Lovely Independent cottage with private pool - Monteguidi cottage sleeps 5

Casole d'Elsa / Monteguidi

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 40 km
  • Swimming pool
  • Child friendly
La Casa Dei Nonni is a beautiful villa located just outside the tiny village of Monteguidi, immersed in the beautiful Tuscan countryside. The villa has a spacious living room with fireplace, a fitted kitchen with a second fireplace, a bedroom with two single beds and a  …see more

from £130 / night

£776 - £1164 / week

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from £130 / night

34

Villa Fonte all'Oppio Pienza - Pienza villa sleeps 13

Province of Siena / Pienza

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Ancient stone farmhouse, nowadays beautiful holiday villa, set in a very panoramic position inside the Parco Artistico Naturale of Val d'Orcia. Only 2 km far we find the well-known Renaissance village of Pienza. In a short drive there are renowned villages such as Monti  …see more

from £204 / night

£1427 - £2331 / week

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from £204 / night

16

Gorgeous 2 bedroom villa in the Val d'Orcia region, features shared pool, private garden and barbecue - Val d'Orcia villa sleeps 4

Montalcino / Val d'Orcia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the Val d'Orcia region south of Siena. This area has been declared a world heritage site by UNESCO. The house is located on a hill with panoramic views over the countryside and only 2 mins from the village of Montisi. Sitting out on your terrazza overloo  …see more

from £74 / night

£518 - £686 / week

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from £74 / night

(1) Excellent 

22

Holiday Apartments near Pienza - Torrita di Siena farmhouse sleeps 3

Province of Siena / Torrita di Siena

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 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 £35 / night

£242 - £509 / week

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from £35 / night

7

Charming rooms with amazing view and breakfast. - San Gimignano b&b sleeps 2

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Conveniently placed between world famous hilltop towns of San Gimignano Florence and Siena. We offer 360° views from the top of a hill surrounded by vines and olive trees. Abundant buffet breakfast and home cooked evening meals are avaialble for our guests, relax by t  …see more

from £82 / night

£544 - £725 / week

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from £82 / night

40

Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Province of Siena / Montepulciano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 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 £95 / night

£518 / week

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from £95 / night

(1) Excellent 

32

I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi - San Giovanni d'Asso villa sleeps 6

Province of Siena / San Giovanni d'Asso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
I MELOGRANI II is a section of a villa settled in the heart of Siena countryside.WHEN THIS PART OF THE HOUSE IS RENTED THE OTHER PART REMAINS CLOSED AND VACANT. This beautiful house is surrounded by a fenced olive grove with private pool (6x 5), lawn, stunning view on  …see more

from £283 / night

£1983 - £2557 / week

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from £283 / night

(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

£305 / week

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from £44 / night

18

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £83 / night

£531 - £635 / week

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from £83 / night

100

Emma - Cipresso - Bagno Vignoni apartment sleeps 4

Province of Siena / Bagno Vignoni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Light and spacious, Cipresso apartment on the first floor of the main house is suitable for up to four guests. It has one large double bedroom and a private bathroom. The other two guests can comfortably sleep on the double sofa bed in the living room. This room is a lo  …see more

from £69 / night

£423 - £604 / week

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from £69 / night

28

Holiday lodging near Pienza P5 - Torrita di Siena apartment sleeps 5

Province of Siena / Torrita di Siena

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 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 £47 / night

£328 - £587 / week

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from £47 / night

20

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

Province of Siena / Pienza

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The farmhouse, set in one of the most fascinating areas of the south of Sienese territory, between Pienza and Montepulciano, shows sober, almost austere lines. Its placing, the group of cypresses, its position on a high ground which raise the whole valley, makes it the  …see more

from £355 / night

£2483 - £3061 / week

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from £355 / night

(1) Very Good 

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £120 / night

£474 - £715 / week

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from £120 / night

(13) Excellent 

20

Tuscan apartment with pool in Cetona - Cetona apartment sleeps 5

Province of Siena / Cetona

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Swimming pool
  • Child friendly
The apartment is ideally situated on the outskirts of the medieval town of Cetona, with a splendid view over the valley and distant mountains. It is a short walk from all the local amenities, including restaurants, cafes, and shops. Within a few minutes you can be among  …see more

from £65 / night

£400 - £600 / week

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from £65 / night

(3) Excellent 

22

Granaio 6 - San Gimignano apartment sleeps 7

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San  …see more

from £36 / night

£250 - £854 / week

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from £36 / night

19

Fern Cottage (v044) - Cetona cottage sleeps 10

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This charming cottage is made up of a kitchen, a living room with fireplace, a dining room, a study, a guest bathroom and a double bedroom with en-suite bathroom with shower on the ground floor. On the first floor there is a double bedroom with en-suite with shower,  …see more

from £324 / night

£2268 - £2664 / week

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from £324 / night

36

Beautiful Tuscan Villa not far from Siena 22 pax - Siena villa sleeps 22

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • 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) you will  …see more

from £475 / night

£2587 - £4311 / week

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from £475 / night

(4) Excellent 

21

Comfort and style in the Siena counrtyside, - Val d'Orcia apartment sleeps 9

Montalcino / Val d'Orcia

4 9 Min stay varies

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

from £235 / night

£1638 - £1988 / week

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from £235 / night

(15) Excellent 

22

Casacorvo Minore *Late Booking Discounts* - Gaiole in Chianti apartment sleeps 4

Province of Siena / Gaiole in Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with sol  …see more

from £85 / night

£525 - £725 / week

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from £85 / night

(1) Excellent 

27

Province of Siena / Poggibonsi

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £61 / night

£366 - £600 / week

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from £61 / night

(2) Excellent 

40

Casa Lorenzo: Charming Tuscan house,pool, AC,WiFi - San Giovanni d'Asso villa sleeps 5

Province of Siena / San Giovanni d'Asso

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Casa Lorenzo is a small indipendent antique house suitable for 5 +1. "what a beautiful charming house you have;we expecially enjoyed the view from the pool ;unparalleded beauty! San Giovanni is a wonderful little town..although we enjoyed all of our day excursion to Mon  …see more

from £207 / night

£1449 - £2018 / week

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from £207 / night

(3) Very Good 

19

Province of Siena / Sovicille

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £48 / night

£276 / week

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from £48 / night

(7) Excellent 

10

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

 …see more

from £39 / night

£483 - £1358 / week

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from £39 / night

(14) Excellent 

24

Charming 2 bedroom Tuscan villa with private pool - San Gimignano villa sleeps 5

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano.The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spend  …see more

from £173 / night

£475 - £1552 / week

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from £173 / night

22

Villa Baiocco - Chiusi villa sleeps 14

Province of Siena / Chiusi

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Villa Baiocco is a typical Tuscan, historic farm house from 1700, recently converted to a prestigious holiday home - without losing its unique character and charm. Surrounded by 20'000m2 of well kept gardens, for your private use only, it offers all the peace and t  …see more

from £248 / night

£1740 - £3914 / week

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from £248 / 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 £146 / night

£1018 - £2578 / week

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from £146 / night

18

galassia 18 - Gaiole in Chianti apartment sleeps 3

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in garage sotter  …see more

from £69 / night

£348 / week

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from £69 / night

15

Lovely 3 bedroom villa in the scenic Tuscan countryside wih large private garden and swimming pool - Montisi villa sleeps 8

Province of Siena / Montisi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Montisi has been restored over the last few years with all the modern facilities within a traditional tuscan villa this makes for a truly unique holiday experience.Located in the scenic Val d'Orcia region which was declared a world heritage site by UNESCO.Thr  …see more

from £148 / night

£1035 - £1250 / week

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from £148 / 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 £690 / night

£4742 - £6466 / week

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from £690 / night

25

Appartamento Glicine - Castelnuovo Berardenga apartment sleeps 7

Province of Siena / Castelnuovo Berardenga

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Le Rocche di Valiano is an ancient village situated in the heart of Chianti area near Siena. The structure, completely surrounded by olives groves, enjoys a spectacular view of the typical Tuscany landscape made by sweet hills and of the vast vineyards. The apartment  …see more

from £55 / night

£384 - £774 / week

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from £55 / night

(2) Very Good 

18

Charming Tuscan farmhouse apartments with pool - Colle di Val d'Elsa farmhouse sleeps 4

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The apartments have been renewed and still have the old local structures such as wood rafters, bricks arches and outside stones walls. They all have their own entrance, a living room with a fully equipped cooking area, one or more bedrooms, TV, an outside area with tabl  …see more

from £78 / night

£432 - £604 / week

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from £78 / night

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