Holiday rentals in Province of Siena: Villas, Cottages and Apartments

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4,208 Holiday homes

1 / 32

Tuscany / Province of Siena / Siena

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £146 / night

£1021 - £1974 / week

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from £146 / night

(3) Very Good 

1 / 24

Villa Gaiole - Gaiole in Chianti villa sleeps 8

Tuscany / Province of Siena / Gaiole in Chianti

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Nearest beach 107 km; Swimming pool; Great for children of all ages ;
Beautiful Family Villa in Borgo di Gaiole, surrounded by the Chianti hills covered in vineyards and olive groves, just a 100 meters walk from the quiet village of Gaiole in Chianti, a typical Tuscan hamlet with restaurants, shops and amenities, an ideally located betwee  …see more

from £81 / night

£567 - £1359 / week

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from £81 / night

(9) Excellent 

1 / 31

Tuscany / Province of Siena / San Giovanni d'Asso

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Great for children of all ages ; Car essential; Air conditioning;
 …see more

from £150 / night

£1050 - £1271 / week

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from £150 / night

1 / 11

Mensanello 5+1 places apt with pool - Colle di Val d'Elsa apartment sleeps 6

Tuscany / Province of Siena / Colle di Val d'Elsa

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
5+1 places apartment composed of a large kitchen with living room, 3 bedrooms and 2 bathroom.We grow grapes, olive-trees, corn and sunflowers, so that the 700 acres of the estate end up by forming a natural and coloured painting. You can taste the Extra-Virgin Olive Oil  …see more

from £100 / night

£500 - £917 / week

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from £100 / night

1 / 100

Casa Daria - La Daria - Guazzino apartment sleeps 2

Tuscany / Province of Siena / Sinalunga / Guazzino

1 bedroomSleeps 23 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 90 km; Great for children of all ages ; No pets allowed;
Exterior Casa Daria is a charming apartment situated in the centre of the town of Bettole, just a few kilometres from the famous Montepulciano and Cortona, in the beautiful area of the Val di Chiana in the South of Tuscany.  The apartment, which can be fo  …see more

from £50 / night

£350 - £438 / week

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from £50 / night

(1) Very Good 

1 / 20

Luxury apartment in Siena, Tuscany - Siena apartment sleeps 4

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Great for children of all ages ; No pets allowed;
Luxury apartment which has been carefully restored, frescoed ceilings and walls, equipped with every comfort, set a short walk from Piazza del Campo, the square of the worldwide Palio of Siena. The apartment is located on the third floor of historical palace in the live  …see more

from £125 / night

£750 / week

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from £125 / night

1 / 7

Charming rooms with amazing view and breakfast.

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
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 £80 / night

£530 - £706 / week

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from £80 / night

(4) Excellent 

1 / 23

Pure 5 star Luxury in Tuscany-Jacuzzi-AC-wifi-S

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
New lower price - one of the nicest flat in Tuscany 5 star standard !!The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with great views over  …see more

from £117 / night

£0 / week

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from £117 / night

1 / 48

La Grancia Country Resort Apt4 - Montisi fort sleeps 3

Tuscany / Province of Siena / Montisi

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from £104 / night

£715 - £794 / week

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from £104 / night

1 / 36

Tuscany / Province of Siena / Montepulciano

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
 …see more

from £59 / night

£334 - £500 / week

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from £59 / night

(5) Excellent 

1 / 33

Torre Farmholiday Tuscan Chianti near Florence

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 35 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £59 / night

£350 - £467 / week

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from £59 / night

(6) Very Good 

1 / 25

Virgilius - Radicondoli villa sleeps 6

Tuscany / Province of Siena / Radicondoli

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 50 km; Swimming pool; Great for children of all ages ;
Situated below the mediaeval village of Radicondoli, this property enjoys an exceptional view over the Chianti hills, taking in the towers of San Gimignano and stretching as far as the Apennines.This self standing villa, surrounded by olives groves and fruit trees, has  …see more

from £60 / night

£417 - £1667 / week

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from £60 / night

1 / 35

Tuscany / Province of Siena / Castelmuzio

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 161 km; Swimming pool; Great for children of all ages ;
 …see more

from £150 / night

£875 - £1250 / week

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from £150 / night

1 / 20

Wisteria Farm (V036) - Pienza farmhouse sleeps 8

Tuscany / Province of Siena / Pienza

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £343 / night

£2400 - £3359 / week

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from £343 / night

(7) Very Good 

1 / 5

TuscanFlat - Siena apartment sleeps 4

Tuscany / Province of Siena / Siena

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 105 km; Not suitable for children; Car not necessary;
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo.You will need to walk up 66 steps to access this apartment, but the effort is amply rewarded by two amazing terraces and their spectacular views. The main living space here is a large,  …see more

from £84 / night

£642 - £1250 / week

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from £84 / night

(2) Excellent 

1 / 22

Balz Tuscan farmholiday Chianti - Radda in Chianti farmhouse sleeps 3

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 35 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic.We restored the farmhouse of the 15th century and Giovanni has personally followed all the work  …see more

from £47 / night

£292 - £375 / week

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from £47 / night

1 / 40

Il Molinaccio di Montepulciano 1 - Montepulciano farmhouse sleeps 2

Tuscany / Province of Siena / Montepulciano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £92 / night

£500 / week

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from £92 / night

(1) Excellent 

1 / 12

Tuscany / Province of Siena / Chianciano Terme

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £179 / night

£1250 - £2250 / week

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from £179 / night

(8) Very Good 

1 / 27

Tuscany / Province of Siena / San Gimignano

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 97 km; Swimming pool; Great for children of all ages ;
 …see more

from £100 / night

£695 - £1377 / week

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from £100 / night

(5) Excellent 

1 / 46

Villa Sangimignano - Montauto farmhouse sleeps 5

Tuscany / Province of Siena / San Gimignano / Montauto

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Nearest beach 80 km; Swimming pool; Great for children of all ages ;
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The house is the r  …see more

from £194 / night

£1417 - £1917 / week

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from £194 / night

1 / 20

Villa Cafaggiola 3 bedroom villa with private pool

Tuscany / Province of Siena / San Gimignano

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 75 km; Swimming pool; Great for children of all ages ;
The Villa has been completely renovated from an old barn and materials have been used for its original restructuring terracotta floors and exposed beams on the ceilings. It 'a great place to spend a quiet holiday without sacrificing the various excursions just a short d  …see more

from £155 / night

£1084 - £1875 / week

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from £155 / night

1 / 100

Castiglione D'orcia 62100 - Castiglione D'Orcia villa sleeps 19

Tuscany / Province of Siena / Castiglione D'Orcia

8 bedroomsSleeps 197 nights min stay

  • 8 bedrooms
  • Sleeps 19
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
Beautiful independent villa with private pool situated in the Orcia valley area, a splendid region south of Siena rich in charming villages and hamlets such us Montalcino, Pienza, San Quirico dOrcia, Castiglione dOrcia. This property has been recently restored and turne  …see more

from £275 / night

£1923 - £3540 / week

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from £275 / night

(1) Excellent 

1 / 14

Tuscany / Province of Siena / Poggibonsi

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
 …see more

from £42 / night

£292 - £584 / week

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from £42 / night

1 / 41

Tuscany / Province of Siena / Siena

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; Air conditioning;
 …see more

from £184 / night

£1284 - £1815 / week

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from £184 / night

(1) Very Good 

1 / 9

Tuscany / Province of Siena / Poggibonsi

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Some pets are welcome - please contact the owner;
 …see more

from £50 / night

£347 - £675 / week

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from £50 / night

1 / 40

Tuscany / Province of Siena / Siena

4 bedroomsSleeps 127 nights min stay

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £200 / night

£1400 - £2475 / week

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from £200 / night

1 / 24

Tuscany / Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Some pets are welcome - please contact the owner;
 …see more

from £81 / night

£567 - £817 / week

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from £81 / night

1 / 20

chianti castle near Siena B3 - Castelnuovo Berardenga apartment sleeps 3

Tuscany / Province of Siena / Castelnuovo Berardenga

1 bedroomSleeps 33 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
These holiday apartments in Tuscany are part of an estate situated in the Chianti Classico area, just 13 km from Siena, surrounded by vineyards and olive groves, in a peaceful place far from the traffic and bustle. The origins of the Castle date back to 1070, but follow  …see more

from £71 / night

£371 - £575 / week

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from £71 / night

1 / 20

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Suitable for children age 5+; No pets allowed;
 …see more

from £76 / night

£531 - £881 / week

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from £76 / night

(3) Excellent 

1 / 29

Tegline Chianti Tuscan holiday accomodation

Tuscany / Province of Siena / Radda in Chianti

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 120 km; Great for children of all ages ;
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from £67 / night

£417 - £542 / week

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from £67 / night

(1) Excellent 

1 / 30

Live Siena from the very top - Siena apartment sleeps 4

Tuscany / Province of Siena / Siena

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Nearest beach 60 km; Great for children of all ages ; Car not necessary;
Treat yourself with a special holiday. Admire a spectacular, unique panorama from a flat that was built not just at the heart of Siena but also on its highest spot. You will be able to see the whole of Siena and all of its surroundings up to Mount Amiata or Chianti'  …see more

from £61 / night

£350 - £560 / week

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from £61 / night

(1) Excellent 

1 / 29

I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi

Tuscany / Province of Siena / San Giovanni d'Asso

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
I MELOGRANI II is a section of a villa settled in the heart of Siena countryside.This section (3 BDR APT) of the beautiful house,surrounded by a fenced olive grove with private pool (6x 5),lawn,stunning view on rolling Tuscan hills consists of a large entrance hall-sit  …see more

from £215 / night

£1500 - £2370 / week

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from £215 / night

1 / 15

Contessa Apt San Gimignano - Larniano apartment sleeps 4

Tuscany / Province of Siena / San Gimignano / Larniano

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Suitable for children age 5+; Car not necessary; Air conditioning;
Lovely Two-roomed apartment (55 mq) with a comfortable terrace for outdoor dinners (10 mq). It is finely furnished with "arte povera toscana" furniture. Living room, separate kitchen corner, bathroom with shower, bedroom with a charming mezzanin floor from whi  …see more

from £74 / night

£517 / week

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from £74 / night

1 / 20

Tuscany / Province of Siena / Sovicille

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Pets welcome;
 …see more

from £99 / night

£690 - £1243 / week

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from £99 / night

1 / 24

25507-Holiday house Siena - Radicondoli villa sleeps 13

Tuscany / Province of Siena / Radicondoli

6 bedroomsSleeps 137 nights min stay

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min stay
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
This property is a typical stone farmhouse recently transformed into an enchanting holiday villa, conveniently located at just 3 km from the characteristic medieval village of Radicondoli. This area, west of Siena is characterized by the gentle rolling hills that extend  …see more

from £115 / night

£800 - £2665 / week

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from £115 / night

1 / 24

Poggibonsi SI - ITC907 - Poggibonsi villa sleeps 2

Tuscany / Province of Siena / Poggibonsi

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Great for children of all ages ; No pets allowed;
This wonderful holiday home in Tuscany has 1 double bed and 1 bathroom, rendering it the ideal living space for a party of 2. For guests' relaxation, there are modern conveniences such as a TV and a washing machine. Couples will find this holiday home the  …see more

from £53 / night

£367 - £517 / week

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from £53 / night

1 / 40

Tuscany / Province of Siena / Montepulciano

4 bedroomsSleeps 97 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min stay
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £219 / night

£1530 - £2605 / week

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from £219 / night

1 / 10

Tuscany / Province of Siena / San Gimignano

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; No pets allowed;
 …see more

from £75 / night

£459 / week

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from £75 / night

(6) Very Good 

1 / 18

Holiday apartment in restored Tuscan farmhouse, sleeps 4, features private garden and shared pool

Tuscany / Province of Siena / San Gimignano

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Great for children of all ages ;
'Podere Torricchi' is a small collection of renovated 16th Century farm buildings converted into luxury houses and apartments. 'Torricchi 6' is a beautiful spacious ground floor house and is located on a hill with stunning views of the Tuscan hills. The renovation has r  …see more

from £75 / night

£525 - £800 / week

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from £75 / night

1 / 14

Tuscany / Province of Siena / San Gimignano / Castel San Gimignano

4 bedroomsSleeps 107 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Great for children of all ages ; Pets welcome;
 …see more

from £143 / night

£1000 - £1409 / week

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from £143 / night

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