Villas with a pool Province of Florence | Apartments to rent with swimming facilities | Holiday Lettings

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Province of Florence

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2,990 Holiday homes

Filters applied: Swimming pool

Travellers going to Province of Florence are booking June dates now. Secure your holiday home today and have the perfect trip.

(2) Excellent 

20

Holiday farmhouse with swimming pool in Greve in Chianti

Province of Florence / Greve in Chianti

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
“wonderful stay, perfect host” We had a wonderful week at Casalone during Aug2016. The house is absolutely charming, renovated with perfect taste, at the end of private road which preserves you from any noisy road or neighbours. Just note that there's  …see more

from £342 / night

£2137 / week

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from £342 / night

(3) Excellent 

40

Holiday villa with swimming pool in Greve in Chianti

Province of Florence / Greve in Chianti

9 18 1 night min

  • 9 bedrooms
  • Sleeps 18
  • 1 night min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly
Villa Benedetta is an elegant, charming Historic residence located within walking distance from the heart of the magnificent village of Greve in Chianti. Featuring 9BR a private swimming pool, a beautiful park and 10,000 sf of living space it is the perfect estate for  …see more

from £642 / night

£5300 - £8975 / week

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from £642 / night

100

Holiday villa rental

Province of Florence / Borgo San Lorenzo

11 22 7 nights min

  • 11 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This wonderful Villa is the perfect place for a relaxing holiday enjoying the peaceful setting and splendid sites in the region and also a brilliant setting for a special occasion or event. There is a reduced rate if less than 16 guests.  …see more

from £570 / night

£3984 - £6356 / week

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from £570 / night

Featured properties

47

Holiday villa rental

Province of Florence / Tavarnelle Val di Pesa

11 20 7 nights min

  • 11 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Immersed in the green countryside of the Chianti hills, surrounded by the typical olive groves and vineyards, Villa Tavarnelle is a centuries old farmhouse which has belonged to the Fusi family for many years now. Recently restored to the highest standards, the villa h  …see more

from £916 / night

£6411 - £11539 / week

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from £916 / night

51

Holiday villa in Certaldo

Province of Florence / Certaldo

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
If you require superior accommodation with an unmistakable touch of class, this fully refurbished, early 19th century, two-storey villa will not disappoint you. It is furnished with valuable antiques dating back to the 1700’s, complemented by elegant, Venetian-des  …see more

from £336 / night

£2351 - £5556 / week

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from £336 / night

24

Holiday villa with swimming pool in Malmantile

Province of Florence / Malmantile

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
This 250 m2 stone villa restored in 1999, is situated separately on the lands of Tenuta San Vito and is surrounded by vineyards. The house consists, on the ground floor, of a large living room with fireplace and a fully equipped kitchen. On the first floor...  …see more

from £313 / night

£2187 - £4461 / week

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from £313 / night

(6) Excellent 

67

Villa rental in Fiesole with swimming pool

Province of Florence / Fiesole

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Like Living in a Postcard” From the moment we walked through the gate of Villa Acacia, my family and I felt at home. The beauty and spaciousness of the home and grounds contributed to the best vacation we had ever had. Mario kindly took us to buy groc  …see more

from £342 / night

£2394 - £4189 / week

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from £342 / night

(8) Excellent 

24

San Donato in Poggio holiday penthouse rental

Tavarnelle Val di Pesa / San Donato in Poggio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This new apartment in Chianti is the perfect place to spend your vacation in total relaxation, taking advantage of all our facilities (swimming pool, etc.). You can easily plan gastronomic tours as well as excursions to some of the most beautiful cities in Tuscany!  …see more

from £73 / night

£364 - £582 / week

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from £73 / night

100

Impruneta holiday villa rental

Province of Florence / Impruneta

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
stunning villa, located in Tuscany Italy, has a max. capacity of 8 people. This stunning villa is perfect for families and friends  …see more

from £182 / night

£1272 - £3373 / week

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from £182 / night

(1) Excellent 

24

Holiday villa with swimming pool in Greve in Chianti

Province of Florence / Greve in Chianti

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Beautiful villa situated in walking distance of the historical main square of Greve in Chianti and other facilities. The villa with private swimming pool and a small garden, was completed in 2010. The main characteristic of the house is its location, facing...  …see more

from £159 / night

£1108 - £2619 / week

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from £159 / night

(8) Excellent 

23

Castelfiorentino holiday apartment rental

Province of Florence / Castelfiorentino

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Lovely villa surrounded by roses” Lovely villa and pool, beautifully kept. Very well equipped and comfortable throughout. Catia and Cinzia are brilliant!  …see more

from £85 / night

£419 - £1170 / week

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from £85 / night

24

Villa letting in Panzano in Chianti with swimming pool

Greve in Chianti / Panzano in Chianti

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
<p><span>This charming Chianti Villa Rental is set in the midst of the gently sloping hills of the Chianti Classico wine-growing region near the village of Panzano.</span></p>  …see more

from £730 / night

£5110 - £6680 / week

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from £730 / night

(6) Very Good 

33

Holiday apartment in San Polo in Chianti

Greve in Chianti / San Polo in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Nice apartment in beautiful setting” Lovely little place in an absolutely stunning setting near the head of a valley. Fabio and his wife (and their dog!) provided a warm welcome and it has an excellent location just a few km south of Florence, but  …see more

from £39 / night

£270 / week

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from £39 / night

18

Holiday villa with swimming pool in Montaione

Province of Florence / Montaione

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
Villa Kora has been built on the rests of one of the watch towers put in defence of the town of Volterra and belonging to the Pucci family who has been ruling this area for centuries. Part of the original tower is still visible as it has been carefully preserved during  …see more

from £341 / night

£2385 - £4231 / week

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from £341 / night

(3) Excellent 

33

Holiday farmhouse with shared pool, golf nearby in Strada in Chianti

Greve in Chianti / Strada in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
We are farmhouse in the Chianti Classico area, in fact we produce red and white wine and also olive oil extravergine and we offer some different flats.We offer apartments for rent with SWIMMING POOL, WIFI FREE IN EVERY HOUSE, FREE INTERNET POINT, INCLUDING AIR CONDITION  …see more

from £73 / night

£483 - £723 / week

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from £73 / night

24

Holiday villa with swimming pool in Castelfiorentino

Province of Florence / Castelfiorentino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly
Single family independent villa from the 1850’s situated in a charming village. Villa Maria is in the small and charming village of Renai, 3 km from Castelfiorentino. The villa is encircled by vineyards and olive groves. The owner Vincenzo realised the restoratio  …see more

from £204 / night

£1428 - £2304 / week

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from £204 / night

24

Holiday apartment in Montagnana Val di Pesa

Montespertoli / Montagnana Val di Pesa

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
The apartament have 1 double bed, 2 two single beds and 1 double sofa bed (sleeps 4+2): apartments of 70 (square meters) at the groundfloor with two bedrooms, one WC/shower, living room with kitchen units and double sofa bed, with independent heating. Kitchen units (ve  …see more

from £120 / night

£684 / week

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from £120 / night

(6) Very Good 

58

Panzano in Chianti holiday apartment rental

Greve in Chianti / Panzano in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
In the wonderful land of Chianti, an ideal starting point for discovering places such as Siena, Florence, San Gimignano, I Casaloni is an old farmhouse that offers its guests apartments with all the comfort and many amenities, such as swimming or Wi Fi. In a warm and we  …see more

from £77 / night

£642 / week

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from £77 / night

(16) Excellent 

36

Villa rental in Barberino Val d'Elsa with swimming pool

Province of Florence / Barberino Val d'Elsa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Carolina is a wonderful 3 bedroom, 3 bath villa situated in the centre of Tuscany in the beautiful wine region between Florence and Siena, just 1 km from the tiny historic hamlet of Linari and 8 km from San Gimignano.  …see more

from £200 / night

£1197 - £2906 / week

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from £200 / night

25

Province of Florence / Greve in Chianti

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £182 / night

£1272 - £2882 / week

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from £182 / night

38

Villa letting in Gambassi Terme with swimming pool

Province of Florence / Gambassi Terme

9 18 7 nights min

  • 9 bedrooms
  • Sleeps 18
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Relax on one of the large private terraces and at sunrise and sunset, when all is calm, you may glimpse the deer, rabbits and pheasants that populate the extensive grounds. Villa Edera is independent, finely restructured and comfortably furnished: everything is at the d  …see more

from £464 / night

£3248 - £4103 / week

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from £464 / night

17

Apartment rental in Marcialla with shared pool

Certaldo / Marcialla

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
La Certaldina Holiday Villa is on the top of a hill in the country side of Chianti An ideal place for a relaxing and peaceful holiday, with the swimming pool surrounded by olive trees and an nice view on the vineyards. The position is perfect as starting point, for  …see more

from £48 / night

£560 - £620 / week

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from £48 / night

(5) Excellent 

67

Greve in Chianti / Lucolena

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

 …see more

from £197 / night

£1368 - £2548 / week

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from £197 / night

42

Greve in Chianti / San Polo in Chianti

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £189 / night

£1317 - £2590 / week

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from £189 / night

24

Holiday villa with swimming pool in Montespertoli

Province of Florence / Montespertoli

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
The villa is situated in a small and charming village called Renai, 3 km from Castelfiorentino, surrounded by vineyards and olive groves. In the small village of Castelfiorentino you will find: railway station, supermarket, banks, post office, pharmacies, hosp...  …see more

from £212 / night

£1479 - £2391 / week

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from £212 / night

(4) Excellent 

13

Holiday bungalow with shared pool in Vinci

Province of Florence / Vinci

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Casa Anita is a bungalow style accommodation with private balcony and private loggia. It is set in a quiet location and affords great views over Vinci and the surrounding countryside. Vinci village is only 1 km away. Great base to explore Tuscany or to relax by the pool  …see more

from £73 / night

£500 - £678 / week

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from £73 / night

24

Villa rental in San Casciano in Val di Pesa with swimming pool

Province of Florence / San Casciano in Val di Pesa

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
This is an independent villa, covering 200 square metres, and extending over two storeys, plus the traditional Tuscan dovecot on its rooftop, now converted into a luxurious bathroom. Although recently fully renovated, the interiors nonetheless retain many typical charac  …see more

from £184 / night

£1283 - £2223 / week

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from £184 / night

56

Villa rental in Barberino Val d'Elsa with swimming pool

Province of Florence / Barberino Val d'Elsa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Poggibonsi holiday accommodation - Located midway between the historic cities of Florence and Siena, in the region known as Barberino Val d'Elsa, this elegant property dates back to the 11th century with a colourful  …see more

from £516 / night

£3610 - £6520 / week

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from £516 / night

11

San Casciano in Val di Pesa holiday apartment rental

Province of Florence / San Casciano in Val di Pesa

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence  …see more

from £250 / night

£1744 - £2214 / week

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from £250 / night

(2) Excellent 

24

San Casciano in Val di Pesa holiday villa rental

Province of Florence / San Casciano in Val di Pesa

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“A beautiful haven” Villa il Portico, a.k.a. Montepaldi a.k.a.Fume - whichever is the proper name - was a slice of paradise and a welcome haven during some unexpected vacation crises. I traveled to Tuscany with extended family, 10 people, and we were a  …see more

from £429 / night

£3000 - £4406 / week

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from £429 / night

48

Villa letting in Tavarnelle Val di Pesa with swimming pool

Province of Florence / Tavarnelle Val di Pesa

11 20 7 nights min

  • 11 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
<p><span class="x_style25">Located in the Chianti region of Italy, just 19 miles south of Florence, Il Capoccio is a large, luxurious property with private wellbeing centre set in a green oasis of olive trees and Mediterranean plants, ideally locat  …see more

from £979 / night

£6850 - £11670 / week

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from £979 / night

(3) Excellent 

51

Holiday farmhouse in Montaione

Province of Florence / Montaione

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
We can arrange horseback riding, wine tours, cooking lessons, bike tours, golf, walking tours In the area there are a lots of farms that produce a very good wines and olive oil and organic farm where you can taste local organic food .  …see more

from £86 / night

£599 - £1881 / week

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from £86 / night

13

Province of Florence / Certaldo

5 12 4 nights min

  • 5 bedrooms
  • Sleeps 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £180 / night

£1197 - £1881 / week

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from £180 / night

(1) Excellent 

100

Apartment rental in Tavarnelle Val di Pesa with shared pool

Province of Florence / Tavarnelle Val di Pesa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
These accommodations hosting 2, 4 and 6 people have kitchen, living room and one, two or three bedrooms. Their bathrooms are equipped with shower.  …see more

from £94 / night

£594 - £1060 / week

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from £94 / night

(2) Excellent 

66

Holiday apartment rental

Greve in Chianti / Panzano in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Ask owner if suitable for children
apartment in farmhouse in the heart of Chianti Classico (Tuscany).La Terrazza.  …see more

from £77 / night

£642 / week

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from £77 / night

(1) Excellent 

33

Strada in Chianti holiday farmhouse rental

Greve in Chianti / Strada in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
We are farmhouse in the Chianti Classico area, in fact we produce red and white wine and also olive oil extravergine and we offer some different flats.We offer apartments for rent with SWIMMING POOL, WIFI FREE IN EVERY HOUSE, FREE INTERNET POINT, INCLUDING AIR CONDITION  …see more

from £75 / night

£495 - £855 / week

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from £75 / night

100

Greve in Chianti holiday villa rental

Province of Florence / Greve in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Villa Turchese is the perfect place for those who want a relaxing getaway in Tuscany, away from the burdens of everyday life.  …see more

from £145 / night

£916 - £1856 / week

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from £145 / night

(8) Very Good 

35

Greve in Chianti holiday farmhouse rental

Province of Florence / Greve in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
We are farmhouse in the Chianti Classico area, in fact we produce red and white wine and also olive oil extravergine and we offer some different flats.We offer apartments for rent with SWIMMING POOL, WIFI FREE IN EVERY HOUSE, FREE INTERNET POINT, INCLUDING AIR CONDITION  …see more

from £60 / night

£398 - £646 / week

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from £60 / night

100

Villa rental in Barberino Val d'Elsa with swimming pool

Province of Florence / Barberino Val d'Elsa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Villa Lucia in Chianti is right in the heart of Tuscany, the ideal location for exploring the region and has a beautiful formal Italian garden and a private pool. A whole range of activities can be organized to make your stay extra special.  …see more

from £424 / night

£2856 - £5339 / week

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from £424 / night

100

Montelupo Fiorentino holiday villa accommodation

Province of Florence / Montelupo Fiorentino

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
This property affords a swimming pool, and large garden, a kitchen, living room, two bedrooms and two bathrooms with shower.  …see more

from £212 / night

£1356 - £2289 / week

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from £212 / night