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

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Province of Arezzo

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2,133 Holiday homes

Filters applied: Swimming pool (2,200)

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

24

Holiday villa with swimming pool in Rapale

Province of Arezzo / Rapale

10 22 7 nights min

  • 10 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This villa is an ancient tuscan villa which was once part of a larger farm in the estate of La Selva. It is a large independent villa with a charming tower and it was recently renovated and brought back to its original splendor; situated about 800 m from the m...  …see more

from £716 / night

£5008 - £5425 / week

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from £716 / night

(24) Excellent 

33

Holiday villa with swimming pool in Poppi

Province of Arezzo / Poppi

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 160 km
  • Swimming pool
  • Child friendly
“Warm welcome, fabulous villa, idyllic setting.” Fantastic welcome from the family. Clean, spacious and full of character. Surrounded by woodland but also great views. On white road about 5km uphill from Poppi, roads a little narrow at times. Pool on  …see more

from £148 / night

£1035 - £2414 / week

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from £148 / night

(12) Excellent 

40

Holiday villa in Castel San Niccolo

Province of Arezzo / Castel San Niccolo

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children age 5+
“Lovely accommodation, setting and hosts, would go back” I stayed here with my husband and our son and his girlfriend, both in their 20's. The accommodation was absolutely lovely, and our son and his girlfriend had a room which was just next to our ac  …see more

from £88 / night

£616 - £1961 / week

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from £88 / night

17

Holiday home with shared pool in Foiano Della Chiana

Province of Arezzo / Foiano Della Chiana

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Beautiful country estate situated in the vicinity of Cortona, a charming medieval town in the south of Tuscany, close to the well-known cities full of art of Siena, Arezzo and Perugia. Along with the cottage Rosa dei Venti, the other two farmsteads comprise five apartme  …see more

from £87 / night

£607 - £1182 / week

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from £87 / night

(2) Excellent 

21

Holiday farmhouse with swimming pool in Cortona

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
“Stunning views, lovely house, helpful owner.” Cortona is a very picturesque medieval town and this villa is a longish walk from the town itself up a very windy road. The house is only a few years old but built in the style of the old houses. It has la  …see more

from £148 / night

£1035 - £1682 / week

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from £148 / night

22

Province of Arezzo / Arezzo

14 30 Min stay varies

  • 14 bedrooms
  • Sleeps 30
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £1380 / night

£5682 - £6337 / week

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from £1380 / night

24

Montebenichi holiday villa rental

Bucine / Montebenichi

11 24 7 nights min

  • 11 bedrooms
  • Sleeps 24
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
This villa is an ancient tuscan villa which was once part of a larger farm in the estate of La Selva. It was recently renovated and brought back to its original splendor; situated about 200 m from the main villa in La Selva. The villa is situated on a small ro...  …see more

from £780 / night

£5454 - £6182 / week

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from £780 / night

100

Holiday apartment with shared pool in Brolio

Castiglion Fiorentino / Brolio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
These apartments located on the ground or first floor offer sitting room, 1 or 2 doubel bedrooms, bathrooms with shower. There is a hall for events, a swimming pool and parking area.  …see more

from £104 / night

£725 - £906 / week

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from £104 / night

18

Apartment rental in Civitella in Val di Chiana

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
Just 40mins from Florence, Siena and Cortona and 20mins from Arezzo. Conveniently situated for many beautiful Tuscan hill towns. We produce our own wine, also our wine tour will introduce you to some of the great wines of the region. We're happy to help and advise  …see more

from £110 / night

£770 / week

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from £110 / night

(3) Very Good 

42

Holiday apartment with shared pool in Montalla

Cortona / Montalla

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 200 km
  • Swimming pool
  • Child friendly
Started officially as a busines in 1994 but with previous experience of property rental in the precedent 10 years, Agriturismo Fontelunga is now a reference poit for those searching for a true Tuscan experience.W own same of the nicest accommodation in the traditio  …see more

from £138 / night

£737 - £1405 / week

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from £138 / night

54

Holiday home in Caprese Michelangelo

Province of Arezzo / Caprese Michelangelo

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Casa Singerna has been converted from a 300-year-old stone barn. Although it has come a long way from its humble beginnings, original features have been retained and materials reused wherever possible to preserve its original character with chestnut beamed ceilings, ha  …see more

from £65 / night

£449 - £2759 / week

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from £65 / night

32

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

(1) Excellent 

14

Cortona / Montanare

3 7 7 nights min

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

 …see more

from £85 / night

£595 - £1337 / week

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from £85 / night

18

Holiday home with shared pool in Castiglion Fiorentino

Province of Arezzo / Castiglion Fiorentino

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 23 km
  • Swimming pool
  • Child friendly
The freshness of this charming garden apartment offering space and easy access to many of Tuscany's hill towns, vineyards and festivals., makes it a good choice for families (or friends) looking for something special and a lovely home in Tuscany  …see more

from £86 / night

£598 - £750 / week

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from £86 / night

100

Holiday villa with swimming pool in Lucignano

Province of Arezzo / Lucignano

9 22 Min stay varies

  • 9 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
Villa Lucignano is a wonderful tuscan villa near Lucignano divided into three adjoining apartments to become a large villa for large groups of people, full of privacy, with private swimming pool, Internet, walking distance to town.  …see more

from £308 / night

£2156 - £4294 / week

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from £308 / night

(34) Excellent 

25

Holiday villa rental

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

(5) Excellent 

1

Holiday villa with swimming pool in Pieve di Chio

Castiglion Fiorentino / Pieve di Chio

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Child friendly
“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 village  …see more

from £225 / night

£1680 - £2048 / week

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from £225 / night

(4) Excellent 

26

Arezzo / Capolona

5 12 Min stay varies

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

 …see more

from £95 / night

£664 / week

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from £95 / night

20

Bibbiena / Casentino

5 6 3 nights min

  • 5 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £173 / night

£1207 / week

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from £173 / night

(12) Excellent 

30

Bibbiena holiday villa rental

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 £242 / night

£1294 - £3363 / week

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from £242 / night

(3) Very Good 

16

Holiday apartment rental

Province of Arezzo / Anghiari

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
“Heaven on Earth” A fantastic place. Lots to do and see. Plenty of great restaurants to sample the excellent Tuscan food. The apartment was just the right size for two people and quickly became our home. The welcome hamper was excellent. Thanks for the  …see more

from £60 / night

£300 - £390 / week

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from £60 / night

(1) Excellent 

24

Province of Arezzo / Bucine

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

 …see more

from £32 / night

£216 - £268 / week

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from £32 / night

100

Holiday villa with swimming pool in Talla

Province of Arezzo / Talla

8 23 Min stay varies

  • 8 bedrooms
  • Sleeps 23
  • Min stay varies
  • Swimming pool
  • Child friendly
This property is a stunning villa set in Tuscany Italy. It has 8 bedrooms and 8 bathrooms, and it is ideal for those who are looking for a memorable experience. This property features: a swimming Pool, an internet Connection, a pet friendly space .  …see more

from £553 / night

£3233 - £4268 / week

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from £553 / night

22

Castiglion Fibocchi holiday apartment let

Province of Arezzo / Castiglion Fibocchi

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
A breathtaking view, an age-old sense of peace and unspoiled nature together with the high level of comfort of the three apartments make this house the ideal destination for those who wish to spend a relaxing holiday in Tuscany.  …see more

from £73 / night

£509 - £880 / week

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from £73 / night

35

Holiday villa with swimming pool in Loro Ciuffenna

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 th  …see more

from £125 / night

£949 / week

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from £125 / night

(54) Excellent 

32

Arezzo holiday villa rental

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Luxury villa located in the heart of Tuscany with wellness centre, large private park, heated swimming pool and fully stocked wine cellar<br />5 suite and 1 standard bedroom, it can give hospitality up to 12+4 persons. Wi-Fi internet connection.  …see more

from £308 / night

£2156 - £3880 / week

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from £308 / night

(53) Excellent 

51

Anghiari holiday villa rental

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly
“Fantastic Holiday Villa” What can I say about Casa Leana and Tuscany? Well it was just one of the best holidays ever! Starting with the friendly service from Di and Leigh who both met us in Anghiari and took us to the villa so that we didn't get l  …see more

from £248 / night

£1730 - £2630 / week

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from £248 / night

40

Holiday farmhouse with shared pool in San Giustino Valdarno

Province of Arezzo / San Giustino Valdarno

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
In addition to enjoying the incomparable view, the quiet, and the exclusivity of the place, you will have the option to switch from the Italian taste of tradition to the Italian taste for fashion, just a few minutes you will find the shop the outlets of Prada and Incisa  …see more

from £125 / night

£863 - £1552 / week

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from £125 / night

(1) Average 

21

Montebenichi holiday villa rental

Bucine / Montebenichi

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 115 km
  • Swimming pool
  • Child friendly
Nice independent house situated on the hillside near the village of Montebenichi in the Chianti area. The place is very quiet and has a beautiful panoramic view of the surroundings, with vineyards, olive groves and woods. Beautiful pool area with a nice panora...  …see more

from £189 / night

£1321 - £2055 / week

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from £189 / 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

(2) Very Good 

32

Holiday villa with swimming pool in Capolona

Arezzo / Capolona

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Caterina is a nice villa with large garden and private swimming pool.Villa Caterina enjoys a spectacular view over the city of Arezzo.  …see more

from £111 / night

£776 / week

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from £111 / night

100

Villa rental in Cavriglia with swimming pool, tennis court

Province of Arezzo / Cavriglia

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
gorgeous villa sleeps 12 people, so it is ideal for a large group of friends and is located in Tuscany Italy. This property is perfect if you seek a relaxing holiday. The villa features: a swimming Pool, an internet Connection, a pet friendly space .  …see more

from £293 / night

£1707 - £2840 / week

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from £293 / night

21

Apartment rental in Stia with swimming pool

Province of Arezzo / Stia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento ORCHIDEALa Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain biking,  …see more

from £82 / night

£569 - £1087 / week

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from £82 / night

(2) Excellent 

60

Holiday villa with shared pool in Ambra

Province of Arezzo / Ambra

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Fantastic place in the heart of Tuscany.Ideal for relax and to visit Florence, Siena, Arezzo, towns and landscape unique in the world (Chianti, Val d'Orcia) famous for wines, olive oil and cheese. Reacheable by public transport.  …see more

from £87 / night

£604 - £694 / week

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from £87 / night

29

Cottage rental in Pietraia with swimming pool

Cortona / Pietraia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Nestled in the colourful Tuscan countryside, just 8km away from the old town of Cortona, Il Nido is a lovely small villa recently restored and finely appointed with a contemporary country-chic style. The skillful ability in matching the soft tones and the tasteful reca  …see more

from £105 / night

£733 - £1725 / week

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from £105 / night

23

Province of Arezzo / Pratovecchio

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £48 / night

£327 - £476 / week

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from £48 / night

(2) Excellent 

21

Stia holiday apartment rental

Province of Arezzo / Stia

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Appartamento GIRASOLELa Fagiana Holiday Rental is in an optimal position. You will be able to fully enjoy the peace and the quietness of the region as well as being in a good position for numerous outdoor activities, such as horse riding, golf, tennis, mountain  …see more

from £95 / night

£664 - £1207 / week

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from £95 / night

(3) Very Good 

24

Holiday apartment with shared pool in Chiusi della Verna

Province of Arezzo / Chiusi della Verna

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
wonderful surroundings, inmidst nature, pool, calm, great garden/lawn, perfect place to spend your holidays with a mixture of relax and cultural tripideal for families or group of friendshiking, mountainbiking, relax, silence, nature, sightseeing, cultural events  …see more

from £50 / night

£319 - £475 / week

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from £50 / night

17

Apartment rental in Foiano Della Chiana with shared pool

Province of Arezzo / Foiano Della Chiana

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Beautiful country estate situated in the vicinity of Cortona, a charming medieval town in the south of Tuscany, close to the well-known cities full of art of Siena, Arezzo and Perugia. Surrounded by picturesque Tuscan countryside, this property comprises three typical s  …see more

from £68 / night

£476 - £893 / week

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from £68 / night

100

Foiano Della Chiana holiday villa rental

Province of Arezzo / Foiano Della Chiana

9 22 7 nights min

  • 9 bedrooms
  • Sleeps 22
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
Villa Grifone is set in the heart of the Chianti countryside near Arezzo, splendidly restored to combine its traditional features with modern amenities the result is a wonderful private property for up to 22 people.  …see more

from £432 / night

£3018 - £5000 / week

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from £432 / night