Province of Arezzo apartment or villa with a private pool area | Holiday Lettings

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949 Holiday homes

Filters applied: Private pool (949)

(53) Excellent 

32

Villa Carda, luxury villa in Tuscany with private heated pool, jacuzzi, sauna and garden, sleeps up to 12 - Arezzo villa sleeps 12

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Located on the hills that divide the Casentino valley from Chianti, the Villa is ideally positioned for those wishing to visit cities such as Florence, Arezzo or Siena.It is also the perfect base to experience and explore the Tuscan countryside.Now restored to perfectio  …see more

from £308 / night

£2156 - £4311 / week

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from £308 / night

(8) Excellent 

41

Villa Seccarille - Anghiari villa sleeps 12

Province of Arezzo / Anghiari

7 12 7 nights min

  • 7 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Exceptional views. Sleeps 12. Pool, gardens, tennis court and basketballOriginally a 16th century farmhouse, Villa Seccarille is situated in 57 hectares of fields and woodlands, on the lower slopes of the Appennine Mountains. The villa offers breathtaking views of the s  …see more

from £358 / night

£2500 - £3750 / week

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from £358 / night

22

Cortona / Bagnolo

5 12 3 nights min

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

 …see more

from £259 / night

£992 - £2199 / week

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from £259 / night

(5) Excellent 

24

Gorgeous five bedroom villa, game room, outdoor p - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Cortonese hillside, La Fortezza and the ancient wall which encloses the town, dominate the view of the surrounding hillside.Guests have exclusive use of the delightful 12x6 swimming pool, with Roman steps, which lies in an extremely panoramic position and from where  …see more

from £145 / night

£1009 - £3138 / week

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from £145 / night

(1) Excellent 

58

Province of Arezzo / Foiano Della Chiana

4 12 5 nights min

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

 …see more

from £302 / night

£1746 / week

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from £302 / night

(2) Excellent 

24

Villa Simpatia - Casentino villa sleeps 21

Bibbiena / Casentino

9 21 7 nights min

  • 9 bedrooms
  • Sleeps 21
  • 7 nights min
  • Nearest beach 123 km
  • Swimming pool
  • Child friendly
Old stone-built farmhouse dating back to the 900s which has been totally renovated into a most comfortable and charming Tuscany holiday accommodation ideal for large groups visiting Italy .The villa, peaceful situated at the foothills of the Apennines within the Casent  …see more

from £401 / night

£2802 - £4634 / week

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from £401 / night

(22) Excellent 

33

Villa in Poppi, Tuscany set in astounding natural surroundings, features private pool, terrace and garden, sleeps 12 - Poppi villa sleeps 12

Province of Arezzo / Poppi

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
Five bedrooms, 4 double bedrooms and one bedroom with two single beds, 3 full bathrooms each with a shower. Large living room with stereo, CD, SAT TV and a large fireplace Many outdoor eating areas - overlooking the castle, overlooking the pool and overlooking the surr  …see more

from £173 / night

£1207 - £1638 / week

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from £173 / night

55

Province of Arezzo / Cavriglia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £183 / night

£1276 - £1940 / week

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from £183 / night

(1) Excellent 

27

Villa Monterosi - Anghiari villa sleeps 8

Province of Arezzo / Anghiari

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Set in 40 acres of olive groves, oak woods and fields full of wild flowers, Villa Monterosi is a jewel of peace with it's own private swimming pool, rolling gardens and terraces. A place to dream of, this stone built house has been renovated to the highest ecolog  …see more

from £173 / night

£863 - £1552 / week

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from £173 / night

53

Villa San Pietro - Cegliolo villa sleeps 10

Cortona / Cegliolo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This stunning villa is located 5 km from Cortona. Recently renovated and nicely furnished, it is an 18th century Tuscan stone house. Surrounded by olive trees and facing south with lovely views across the valley below, Villa San Pietro is very private and quiet with tra  …see more

from £296 / night

£2069 - £3535 / week

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from £296 / night

(1) Excellent 

24

Beautiful villa with pool and amazing Tuscan view - Cortona villa sleeps 10

Province of Arezzo / Cortona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 161 km
  • Swimming pool
  • Child friendly
Villa Cortona is a beautifully restored luxury tuscan villa with 5 double bedrooms and 6 bathrooms.Each bedroom has its own different style and character and en-suite bathroom with wonderful views.The interior of Villa Cortona is large, bright and spacious, with two lar  …see more

from £419 / night

£2932 - £4656 / week

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from £419 / night

21

Villa with pool near Cortona - Castiglion Fiorentino villa sleeps 8

Province of Arezzo / Castiglion Fiorentino

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely stone villa is located on the hills between Arezzo (18km) and Cortona (12km), only few minutes from Castiglion Fiorentino (3km), a lovely medieval village dominating the green valleys of the Val di Chio and the Val di Chiana. This strategic position offers  …see more

from £259 / night

£1294 - £2587 / week

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from £259 / night

(2) Excellent 

21

Villa Cicaleta within walking distance to Cortona - Cortona farmhouse sleeps 7

Province of Arezzo / Cortona

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
Surrounded by olive groves and a 3000sqm private garden, the fenced-in holiday villa offers absolute peace and quiet at only 1,5 kilometres from the Etruscan Cortona, which can be easily reached on foot. The Trasimeno lake with its nice beaches and islands is at 8km and  …see more

from £148 / night

£1035 / week

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from £148 / night

21

Tuscan Villa With Private Pool And Amazing Views - Lucignano villa sleeps 8

Province of Arezzo / Lucignano

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Casa Luisa is a completely refurbished 3 bedroom property. It is located between Lucignano and Sinalunga, about 10 mins from the A1 Betolle toll. The houses in the tiny hamlet are mainly farms and the sheep one can hear in the distance have bells around their necks and  …see more

from £108 / night

£750 - £2200 / week

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from £108 / night

(8) Excellent 

24

Peaceful 6 bedroom Tuscan villa with private outdoor pool and amazing views - Monte San Savino villa sleeps 11

Province of Arezzo / Monte San Savino

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa al Monte is uniquely situated on the edge of the medieval hamlet Monte San Savino, in a peaceful panoramic position with views of 180° of the surrounding countryside. This ancient home has been finely and elegantly restored with every modern comfort and lies in a  …see more

from £137 / night

£953 - £2802 / week

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from £137 / night

(3) Very Good 

23

3 bedroom hilltop farmhouse with stunning views of Tuscan landscape, private swimming pool, shaded terrace, children welcome - Anghiari farmhouse sleeps 6

Province of Arezzo / Anghiari

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
It is in an outstanding hilltop position 500 metres above sea level with stunning views of up to 30-40 miles in 3 directions to distant hills and mountains. It stands in 4 acres of grounds of which one acre is woods.Meaccino is a very beautiful stone farmhouse dating fr  …see more

from £35 / night

£250 - £500 / week

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from £35 / night

(1) Excellent 

27

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £86 / night

£561 - £819 / week

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from £86 / night

(2) Excellent 

26

Province of Arezzo / Terranuova Bracciolini

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £259 / night

£1811 - £3621 / week

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from £259 / night

(32) Excellent 

24

Tuscan Villa. Borgo Valecchie. Cortona - Montanare villa sleeps 10

Cortona / Montanare

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 180 km
  • Swimming pool
  • Child friendly
Our villa offers an ideal combination of elegant simplicity and historical charm which create a unique experience and can comfortably accommodate up to 10 guests. Located just five minutes away from The Hill town Cortona. Along with a private swimming pool, this holida  …see more

from £203 / night

£1423 - £2544 / week

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from £203 / night

100

Capolona 64805 - Talla villa sleeps 23

Province of Arezzo / Talla

8 23 Min stay varies

  • 8 bedrooms
  • Sleeps 23
  • Min stay varies
  • Swimming pool
  • Child friendly
Beautiful farmhouse situated in the country-side area surrounding the nice town of Arezzo (18 km away). This villa has been completely restored and turned into a welcoming accommodation allowing up to 23 guests. This property offers a main villa and 2 restored former ba  …see more

from £559 / night

£3265 - £4310 / week

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from £559 / night

(11) Excellent 

30

Villa di Catarsena, comfortable with heated pool - Bibbiena villa sleeps 14

Province of Arezzo / Bibbiena

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
The Villa, constructed at the end of the 18th century, offers a relaxing and comfortable stay to whoever wishes to spend their holidays in Tuscany. The Villa has been furnished in a very comfortable way with quality furniture, in part antique and in part in stile, creat  …see more

from £276 / night

£1932 / week

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from £276 / night

(12) Excellent 

21

Rustic Tuscan farmhouse in the town of Cortona with gorgeous views, swimming pool, private garden and barbecue - Cortona farmhouse sleeps 8

Province of Arezzo / Cortona

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
This charming Tuscan Farmhouse is set in a lovely, unspoilt region near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields. Casa Al Campo has 2 acres of unfenced land including its own private vineyard, two terraces and plenty of shaded seating  …see more

from £214 / night

£1492 - £3276 / week

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from £214 / night

26

Sasso Orlando - Terranuova Bracciolini house sleeps 10

Province of Arezzo / Terranuova Bracciolini

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Sasso Orlando is an old stone farmhouse in the countryside of Valdarno Aretino at the foot of the mountain range of Pratomagno. The cottage was recently restored with great care and taste using materials of high value. The wooden ceilings, old brick arches, old terracot  …see more

from £113 / night

£819 - £1682 / week

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from £113 / night

12

Col di leccio, beautiful panoramic stone cottage - Cortona cottage sleeps 10

Province of Arezzo / Cortona

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Col di Leccio is a beautiful property made up of two stone cottages which enjoy a wonderful hilly position, a few minutes from the medieval town Cortona. Each house consists of two floors which host a cosy siting room with sofa and tv, dining area, fully fitted kitchen,  …see more

from £186 / night

£1294 - £2156 / week

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from £186 / night

(2) Excellent 

32

Il Mulino - Farmhouse with pool near Lucignano - Lucignano farmhouse sleeps 10

Province of Arezzo / Lucignano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Mulino in Italian means Mill and this house used to be the mill of the estate. It still retains some of the original features including the two long stone walls which used to channel the water from a nearby stream towards the mill. Today these two walls form a natural e  …see more

from £448 / night

£3130 - £3819 / week

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from £448 / night

(1) Excellent 

15

Restored, classic Tuscan farmhouse with pool and jacuzzi in the village of Monte San Savino - Monte San Savino apartment sleeps 7

Province of Arezzo / Monte San Savino

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
Country farm-house completely restored in the village of Monte San Savino, immersed in the Touscany country near Arezzo, Siena e Cortona, only 4 km of walk far from the castle of Gargonza. Inside simple but comfortable bedrooms with a sight beams, television and a livin  …see more

from £61 / night

£604 - £863 / week

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from £61 / night

(1) Excellent 

20

Province of Arezzo / Arezzo

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £138 / night

£863 - £1466 / week

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from £138 / night

33

Province of Arezzo / Loro Ciuffenna

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

 …see more

from £37 / night

£250 - £432 / week

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from £37 / night

16

Casina Vereno - Bagnolo villa sleeps 4

Cortona / Bagnolo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This charming independent villa is situated in panoramic position in the Cortonese Mountains above the Etruscan hill town of Cortona. It's ideal location make it easy visit the most renowned historical and art cities of Tuscany and Umbria. The property, with privat  …see more

from £150 / night

£1048 - £1419 / week

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from £150 / night

20

Teresa Villa Overlooking a Breathtaking Landscape - Cortona villa sleeps 8

Province of Arezzo / Cortona

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Teresa is a pretty villa with a wonderful view on Cortona valley, completely renovated and equipped with every comfort. Very near to the nice town of Cortona, this wonderful structure overlooks on a breathtaking landscape and it is situated short distance from a s  …see more

from £185 / night

£1294 - £2716 / week

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from £185 / night

28

Villa Petrolo, Petrolo winery - San Leolino villa sleeps 33

Bucine / San Leolino

16 33 Min stay varies

  • 16 bedrooms
  • Sleeps 33
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Petrolo is the 18th century manor house of the Petrolo winery, built by Massimiliano Soldani, architect sculptor and medalist for the Medici Family, as his own residence. It's now available for holidays, weddings and events.The property can host from 17 to 3  …see more

from £970 / night

£6363 - £10673 / week

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from £970 / night

6

Province of Arezzo / Castelluccio, Arezzo

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £87 / night

£423 - £682 / week

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from £87 / night

(3) Excellent 

31

Province of Arezzo / Badia Agnano

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £216 / night

£1509 - £3440 / week

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from £216 / night

16

Province of Arezzo / Arezzo

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 145 km
  • Swimming pool
  • Child friendly

 …see more

from £85 / night

£561 - £888 / week

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from £85 / night

(2) Excellent 

25

Casa Gorgacce - Mercatale di Cortona house sleeps 6

Cortona / Mercatale di Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 22 km
  • Swimming pool
  • Child friendly
Casa Gorgacce is an old stone farmhouse with lots of character beautifully converted with all modern comforts. It has a private garden and pool, complete privacy yet with great access and only a few kilometres from 2 lively villages; Meratale di Cortona and Lisciano Nic  …see more

from £130 / night

£873 - £1550 / week

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from £130 / night

19

Farmhouse apartment "The Loft" w/pool & garden - Loro Ciuffenna apartment sleeps 3

Province of Arezzo / Loro Ciuffenna

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
** TRIP ADVISOR 2014 CERTIFICATE OF EXCELLENCE WINNER **Beautiful, independent self-catering apartment in ancient Tuscan farmhouse with private swimming pool.The house is on a 30 acres property on the slopes of Pratomagno mountain, between Florence and Arezzo (35 km fro  …see more

from £72 / night

£311 - £444 / week

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from £72 / night

35

Villa in the Chianti hills - Malva villa sleeps 14

Loro Ciuffenna / Malva

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
For those who love nature and the Tuscany countryside, our country villa “Oliveta” is the ideal holiday destination in Tuscany. The villa is located on the Aretine Chianti hills, in a lovely countryside area at the foot of Pratomagno mountain and along to the histor  …see more

from £125 / night

£949 - £1725 / week

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from £125 / night

25

Province of Arezzo / Anghiari

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £104 / night

£690 / week

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from £104 / night

(12) Excellent 

45

Tuscan villa in spectaular location with incredible heated pool, gym and jacuzzi - Castel San Niccolo villa sleeps 7

Province of Arezzo / Castel San Niccolo

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children age 5+
We are spectacularly located in a prominent elevated position in a South facing valley which brings long hours of sunshine and a favourable micro climate. The house is approached by a lane which winds its way from the main road, crossing over a river by an ancient bridg  …see more

from £104 / night

£725 - £4680 / week

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from £104 / night

18

Casa del Tramonto (House of the Sunset) 3 apts. - Civitella in Val di Chiana apartment sleeps 2

Province of Arezzo / Civitella in Val di Chiana

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Private garden
Casa del Tramonto (House of the Sunset) is situated in an idyllic position on a hillside promontory with breathtaking views over the rolling hills of Chianti. The building itself is reported to be a monastery dating from the 14th century, and has been restored using the  …see more

from £110 / night

£770 / week

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from £110 / night

Top Destination reviews

Sansepolcro Garden apartment
Revisiting the magic of Sansepolcro

Though this was our first stay at Louise and Franco's wonderful house, it was our third visit to Sansepolcro. The garden apartment was spacious,comfortable and quintessentially Italian and though the March weather didn't lend itself to our using the … see more
Casa dei Sogni, Stefano - An attractive air conditioned stone farmhouse with Private Pool - set within a small Tuscan borgo
Not to be missed

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Spacious and airy Volta Apartment - 2 bedrooms
Excellent apartment with friendly owner

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Casa Dei Sogni, Tuscan Villa, Private Pool, A/C
Not to be missed

This Tuscan farmhouse has been tastefully and sympathetically restored. It is situated at the top of the valley with spectacular views of the surrounding countryside. You do need a car to stay here but most of the towns and villages to be explored … see more
To Stones
Amazing Home Away From Home

The best first impression was to be greeted late at night by Ester and her partner in the dark and in poor weather just so we could find a parking spot and get situated in the property. Ester was amazing and has gone to great lengths to ensure her ho … see more
Stunning Tuscan villa with five bedrooms, private
A true TUSCAN experience. Better than words can describe.

It is quite a challenge to put into words a description of this place, the family and the amazing time we had at Vila Papale. The house and the entire property has so much history and character making this place a unforgettable experience. The garden … see more

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