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  • Italy
  • Tuscany
  • Province of Arezzo
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  • Anghiari (2)
  • Arezzo (5)
  • Camaldoli (1)
  • Caprese Michelangelo (1)
  • Castel San Niccolo (2)
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  • Cortona (31)
  • Loro Ciuffenna (3)
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  • Monte San Savino (1)
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  • Rigutino (1)
  • San Giovanni Valdarno (1)
  • Sansepolcro (1)
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56 Holiday homes

Filters applied: Nightlife (56)

47

Casa vacanze Alle porte del Chianti - San Giovanni Valdarno apartment sleeps 7

Province of Arezzo / San Giovanni Valdarno

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Nearest beach 120 km
  • Child friendly
  • Ask about pets
The Apartment is located in the heart of the historic centre of San Giovanni hometown of the famous painter Masaccio. The apartment is located in Tuscany, near the Chianti area, between Florence, Siena and Arezzo. The area is very quiet and is a suitable choice for a r  …see more

from £70 / night

£487 / week

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from £70 / night

(52) Excellent 

51

Casa Leana - Farmhouse - HEATED Pool & Games Room - Anghiari villa sleeps 10

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 66 km
  • Swimming pool
  • Child friendly
Currently offering 15% discount for the only week left in 2016. Casa Leana is over 350 years old and brimming with gorgeous original features from chunky beamed, wood ceilings and exposed stone walls to the traditional tiled kitchen. We have also lavished a whole lot  …see more

from £248 / night

£1730 - £2630 / week

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from £248 / night

(6) Excellent 

40

Casa Terrazza: Grand Tuscan house in medieval village with large terrace for alfresco dining, sleeps 7 - Lucignano house sleeps 7

Province of Arezzo / Lucignano

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Casa Terrazza is located in Lucignano, one of the most outstanding examples of a fortified Tuscan mediaeval village. Casa Terrazza, is just a few steps away from restaurants and cafes.. Featuring a large terrace opening off main living area with views of the Val di Chi  …see more

from £130 / night

£853 - £1259 / week

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from £130 / night

(3) Very Good 

42

La Bozza , country apartment with private garden - Montalla apartment sleeps 8

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 traditional  …see more

from £140 / night

£743 - £1417 / week

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from £140 / night

(9) Excellent 

33

Villa Rosa - Heaven in Tuscany|Pool|WiFi|Cortona - Cortona villa sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
With essential private pool and (Free) Wi-Fi, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vibrant Cortona. Couples love it, families love it. It is heaven. A two bedroom, two bathrooms, fully furnished beautiful  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(9) Excellent 

32

Cortona, Tuscan Retreat, Serene, WiFi, Pool, Bliss - Cortona house sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
Your holiday to Tuscany is special. You want a home that will provide you with the essential pool and of course the internet. You want to be close to the amenities but far enough away for privacy, seclusion and relaxation. We would love to welcome you to Villa Rosa w  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(1) Excellent 

24

Il Moro Novo - Montalla apartment sleeps 3

Cortona / Montalla

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Equipped with chairs, shades, and beach beds.It has been restored with respect for the original stile and all the furniture are antique, you will have a warm and relaxing feeling when you enter Il Moro Novo.The house is located just outside a small country village, so i  …see more

from £61 / night

£320 - £603 / week

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from £61 / night

(2) Excellent 

10

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

 …see more

from £79 / night

£522 - £1066 / week

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from £79 / night

(5) Excellent 

30

Villa le Celle del Farinaio: Tuscan home with stunning valley views, swimming pool and trampoline, sleeps fourteen - Farinaio villa sleeps 14

Cortona / Farinaio

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
The cells of the villa Farinaio is situated in a beautiful hilly which overlooks the valley below and it is surrounded by green woods of our own property where you can find numerous hiking trails with different difficulty levels for taking a walk. The villa is completel  …see more

from £187 / night

£1305 - £2609 / week

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from £187 / night

(9) Excellent 

38

Tuscan Dream|Private|Pool|Walk to Cortona|FreeWiFi - Cortona cottage sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
A dream home just for you. We created our home in Cortona with all the essential mod cons. Music, Kitchen, comfy beds, and of course with the essential pool and (FREE) Wi-Fi. Villa Rosa is nestled into the Cortona (Tuscan) hillside with only a few minutes drive to  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(1) Excellent 

20

Le Casine - Lavanda Apartment - Fratta Santa Caterina apartment sleeps 3

Cortona / Fratta Santa Caterina

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £50 / night

£390 - £523 / week

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from £50 / night

79

Cortona / Centoia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 16 km
  • Swimming pool

 …see more

from £105 / night

£679 - £1035 / week

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from £105 / night

(1) Excellent 

21

Province of Arezzo / Loro Ciuffenna

11 20 Min stay varies

  • 11 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

 …see more

from £218 / night

£1522 - £3044 / week

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from £218 / night

(4) Excellent 

30

Tuscany, Cortona - Villa Under The Sun - Gorgeous - Cortona house sleeps 5

Province of Arezzo / Cortona

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
A two bedroom, two bathrooms, fully furnished beautiful private house for your Tuscan holiday. Complete with the essential private sparkling pool and Wi-Fi connection, Villa Rosa is nestled into the Tuscan hillside within a few minutes drive or leisurely walk into vib  …see more

from £235 / night

£1645 - £2023 / week

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from £235 / night

(2) Very Good 

19

Le Casine - Limone Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £63 / night

£438 - £600 / week

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from £63 / night

(7) Excellent 

33

Two villas at the top of Tuscan hills, near Arezzo - Arezzo house sleeps 6

Province of Arezzo / Arezzo

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on top of a small hill, set in beautiful unspoiled Tuscan countryside and within walking distance from the charming medieval town of Arezzo, this beautiful property (and swimming pool) commands amazing views from its terraces and gardens. Composed by Casa PADRON  …see more

from £140 / night

£914 / week

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from £140 / night

(1) Excellent 

19

Le Casine - Olivo Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

23

Detached villa with private pool near Arezzo - Arezzo villa sleeps 11

Province of Arezzo / Arezzo

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The villa lies in the heart of the Tuscan hills (12 Kms from the city of Arezzo), around 400 meters above the sea level, in a very quiet place with nice panoramic views. Ideally positioned to visit the most beautiful towns & villages of centre/southern Tuscany (as A  …see more

from £192 / night

£1253 - £2522 / week

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from £192 / night

35

Casa Fontelunga, ancient tuscan villa with pool - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Casa Fontelunga is a lovely country house placed in an enchanted location hillside, between our olive plantation and just a few minutes from the beautiful art city of Cortona, made famous worldwide from the book and movie 'Under the Tuscan Sun'.Privacy and qui  …see more

from £201 / night

£1174 - £1957 / week

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from £201 / night

20

Charming Tuscan holiday farmhouse in the Castel San Niccolo commune, sleeps up to 8 and features private pool and jacuzzi - Castel San Niccolo farmhouse sleeps 8

Province of Arezzo / Castel San Niccolo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
La Magnana offers the perfect holidays to relax your body and mind while you'll be strolling in the fantastic National Park of « La Foresta Casentinese » on the Tuscan Apennines. You'll visit the closest cities : Firenze, Arezzo, Siena and Pisa. Or you'  …see more

from £61 / night

£392 - £870 / week

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from £61 / night

(1) Excellent 

11

Province of Arezzo / Loro Ciuffenna

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Ask about pets

 …see more

from £85 / night

£592 - £1174 / week

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from £85 / night

(21) Excellent 

27

Villa Mondello in Tuscany, great view on the hills - Castel San Niccolo villa sleeps 12

Province of Arezzo / Castel San Niccolo

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Mondello is a stone construction, with frescoed interns and has been recently restored, having in total 6 bedrooms and 5 bathrooms. It is in the Tuscan countryside a few km from Florence and Arezzo, as well as the countless sites closer by, and is thus apt for tho  …see more

from £162 / night

£1740 - £3392 / week

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from £162 / night

17

Province of Arezzo / Cortona

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

from £66 / night

£444 - £505 / week

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from £66 / night

14

Province of Arezzo / Loro Ciuffenna

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly

 …see more

from £53 / night

£374 - £722 / week

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from £53 / night

(2) Excellent 

65

17th century farmhouse with pool, A/C and Wi-Fi - Tregozzano villa sleeps 10

Province of Arezzo / Tregozzano

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
La Rustica is an old farmhouse originally built in stone in 1695 and situated on the outskirts of Arezzo which can be easily reached by public transport giving the guests the double advantage of country living and a urban environment. It is a villa rich of history equip  …see more

from £107 / night

£748 - £1305 / week

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from £107 / night

(1) Excellent 

9

Province of Arezzo / Caprese Michelangelo

8 18 Min stay varies

  • 8 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £470 / night

£2696 / week

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from £470 / night

(1) Excellent 

83

Province of Arezzo / Cortona

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £87 / night

£522 - £853 / week

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from £87 / night

10

Province of Arezzo / Monte San Savino

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly

 …see more

from £70 / night

£487 / week

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from £70 / night

16

Le Casine - Girasole Apartment - Fratta Santa Caterina apartment sleeps 4

Cortona / Fratta Santa Caterina

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £59 / night

£409 - £552 / week

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from £59 / night

(1) Excellent 

16

Relax in Penisola Sorrentina - Camaldoli apartment sleeps 8

Province of Arezzo / Camaldoli

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly
The villa is located in a small,picturesque and very peaceful town called Patierno,in Vico Equense.Surrounded by vegetation,you enter the villa througt a garden full of flowers.The flat is at the first floor,about 110 m;it has two tastefully furnished bedrooms,two bat  …see more

Pricing unknown

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Pricing unknown

(35) Excellent 

30

Il Villino di Cortona (Property at exclusive use) - Cortona villa sleeps 4

Province of Arezzo / Cortona

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
"Il Villino di Cortona", cosy holiday home nestled in the green heart of the Chiana Valley in Cortona (Tuscany), an oasis of peace, tranquility and relaxation. Your holiday in contact with nature ... "Il Villino di Cortona”, is a small holiday home, nestled in the Va  …see more

from £83 / night

£531 - £748 / week

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from £83 / night

(2) Excellent 

88

Province of Arezzo / Cortona

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 18 km
  • Swimming pool
  • Child friendly

 …see more

from £105 / night

£609 - £1035 / week

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from £105 / night

19

Le Casine - Mela Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

(2) Excellent 

24

Villa Vallibona - Castiglion Fiorentino villa sleeps 11

Province of Arezzo / Castiglion Fiorentino

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 128 km
  • Swimming pool
  • Child friendly
Villa Vallibona is situated in the midst of peace and greenery in the gentle hills between Castiglion Fiorentino and Cortona, among olive groves and fruit trees, in a splendid panoramic position. The extensive property includes the main villa and the pool. Villa Vallibo  …see more

from £187 / night

£1305 - £2174 / week

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from £187 / night

101

Province of Arezzo / Cortona

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 17 km
  • Swimming pool

 …see more

from £522 / night

£3653 - £5740 / week

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from £522 / night

(1) Excellent 

12

Large Tuscan farmhouse apartment in beautiful Cortona countryside, four bedrooms, pool access - Cortona farmhouse sleeps 6

Province of Arezzo / Cortona

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The apartment is independent, and has beautiful piece of ancient furniture own heating system, some of them has a fire-place. This has a own outside space and very well fitted out with garden furniture, all equipped with every thing necessary to be efficient and functi  …see more

Pricing unknown

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Pricing unknown

15

Le Casine - Papavero Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £54 / night

£371 - £495 / week

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from £54 / night

14

Le Casine - Bugia Apartment - Fratta Santa Caterina apartment sleeps 2

Cortona / Fratta Santa Caterina

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
This recently renovated country villa is situated in a beautiful rural setting, nestled in a village in the valley below the Etruscan town of Cortona. It has been converted, in traditional Tuscan style, into seven fully-self-contained, apartments which sleep between 2 t  …see more

from £51 / night

£352 - £466 / week

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from £51 / night

(1) Excellent 

48

Podere Le Cantine - Lucignano farmhouse sleeps 28

Province of Arezzo / Lucignano

10 28 Min stay varies

  • 10 bedrooms
  • Sleeps 28
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
This recently renovated, converted farmhouse in warm, honey-coloured Tuscan stone and brick, stands in an elevated position overlooking the lawns of the pool terrace below and open fields and woodland dotted with Cypress trees beyond, with no other buildings in sight. I  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

11

Province of Arezzo / Arezzo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Car not necessary
  • Air conditioning

 …see more

from £70 / night

£435 / week

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from £70 / night

Top Destination reviews

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

We had a very warm welcome through Louise and her husband. What a wondeful flat, very spacious, lots of rooms and very much light through large windows. Louzise even purchased wine and some basic fod for the first days which was VERY generous and was … 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

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
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
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
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

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