Walking holiday villas and apartments Province of Arezzo | Holiday Lettings

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885 Holiday homes

Filters applied: Walking holidays (885)

(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

(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

AGRITURISMO CASAVECCHIA-NIBBIO Castiglion Fibocchi - Castiglion Fibocchi apartment sleeps 6

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. The beauty of natural surroundings, the h  …see more

from £73 / night

£509 - £880 / week

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from £73 / night

20

Peacock Manor (v020) - Foiano Della Chiana manor house sleeps 26

Province of Arezzo / Foiano Della Chiana

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
An independent residence (sleeps 24+2) divided into 6 apartments and on the ground floor a large communal lounge with a fireplace, kitchenette with oven and dishwasher, washing machine.Peony (sleeps 4) on the ground floor, there is a living room with a kitchenette with  …see more

from £518 / night

£3621 - £4138 / week

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from £518 / 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 £129 / night

£845 - £1248 / week

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from £129 / 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

(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 - £1294 / week

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from £148 / night

(6) Excellent 

15

Extraordinary Tower in the Tuscan hills with pool, - Sansepolcro tower sleeps 3

Province of Arezzo / Sansepolcro

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
Torre the Brancialino nestles beautifully in the Tuscan Hills some 10 kilometres from the Renaissance town of Sansepolcro.Being part of a remarkably restored medieval castle (where the owner lives) the tower offers the perfect romantic hideaway with comfortable accommod  …see more

from £50 / night

£350 - £420 / week

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from £50 / night

(12) Excellent 

17

Borgo il Vepri - Ambra apartment sleeps 4

Province of Arezzo / Ambra

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Vepri is the perfect base for a tranquil holiday or home in the sun.It is for the discerning-a quiet and gated private luxury development comprising a small number of apartments and townhouses surrounding a communal piazza.The swimming pool is simply wonderful, set amid  …see more

from £43 / night

£295 - £479 / week

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from £43 / night

(1) Excellent 

4

Villa Sonia, Cortona Tuscany - Cortona villa sleeps 6

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
Villa Sonia is for sure, a really special property tucked away on the sleepy hillside of Cortona and, just a short distance form the enchanting franciscan monastery of Le Celle. Villa Sonia is perfect for four to 12 guests.This ancient stone farmhouse dates back to the  …see more

from £209 / night

£1457 - £1465 / week

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from £209 / night

28

Appartamento Giardino Centro - Lucignano apartment sleeps 4

Province of Arezzo / Lucignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
A fully self-contained apartment located in a medieval building opening onto its own garden, right in the centre of the charming central Tuscan town of Lucicnano.Appartamento Giardino is located in a a converted frantoio, olive oil mill is the centre of the medieval tow  …see more

from £72 / night

£457 - £645 / week

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from £72 / night

16

Province of Arezzo / Badia Tedalda

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 85 km
  • Child friendly

 …see more

from £38 / night

£259 / week

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from £38 / night

28

Province of Arezzo / Castiglion Fibocchi

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £26 / night

£182 / week

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from £26 / night

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 £69 / night

£483 / week

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from £69 / night

(3) Very Good 

10

Province of Arezzo / Bibbiena

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets

 …see more

from £50 / night

£518 / week

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from £50 / night

(32) Excellent 

21

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

(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 £78 / night

£518 - £1057 / week

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from £78 / 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

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

(2) Very Good 

24

Villa il Rocolo - Arezzo villa sleeps 12

Province of Arezzo / Arezzo

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The villa has been lovingly restored and transformed into a most elegant and refined holiday home in keeping with the original tradition and character of this charming stone villa, with wood beams and vaulted terra cotta ceilings.In the private gardens you will find a 1  …see more

from £177 / night

£1238 - £2802 / week

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from £177 / night

(17) Excellent 

24

Cortona / Montecchio, San Lorenzo

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £39 / night

£272 / week

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from £39 / night

37

Garibaldi, splendid apt in the centre Cortona - Cortona apartment sleeps 6

Province of Arezzo / Cortona

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Garibaldi is a finely furnished and welcoming apartment, located on the first floor of a historic building having the same name of the Piazza that leads into the promenade in the centre of Cortona. The architecture of each area is enhanced by the choice of tones and fur  …see more

from £87 / night

£647 - £733 / week

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from £87 / night

(1) Excellent 

14

Luxury Tuscan Holiday Home , Stalla Rustica - Cortona house sleeps 8

Province of Arezzo / Cortona

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
An elegant, 17th Century Tuscan Farmhouse in a glorious location among Tuscan and Umbrian hills, only minutes from the beautiful Etruscan walled town of Cortona. Perfect all year round: walk or cycle in the hills, soak at the Thermal Spa, shop in fresh produce markets,  …see more

from £250 / night

£1495 / week

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from £250 / 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

(1) Excellent 

80

Province of Arezzo / Cortona

2 6 1 night min

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

 …see more

from £104 / night

£690 - £1026 / week

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from £104 / night

(4) Excellent 

13

Impressive stone built Tuscan holiday villa with private grounds and swimminig pool, sleeps 10 - Castiglion Fiorentino villa sleeps 10

Province of Arezzo / Castiglion Fiorentino

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 27 km
  • Swimming pool
  • Child friendly
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in one  …see more

from £190 / night

£1330 / week

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from £190 / night

(2) Excellent 

20

Province of Arezzo / Pian di Sco

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £44 / night

£285 - £406 / week

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from £44 / 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

(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

(4) Very Good 

20

Province of Arezzo / Pratovecchio

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly

 …see more

from £69 / night

£432 / week

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from £69 / night

(1) Excellent 

24

Casa dei Noce - Pieve Santo Stefano villa sleeps 8

Province of Arezzo / Pieve Santo Stefano

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
We bought the house back in 2004 as a ruin and spent the next 3 years creating a house that we ourselves would love to stay in and we are very proud of it The house is the last one up the valley with no near neighbours and has wonderful views which you can never tire of  …see more

from £150 / night

£1000 - £1480 / week

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from £150 / night

(3) Good 

24

The Hut. Villa with pool - San Giustino Valdarno villa sleeps 4

Province of Arezzo / San Giustino Valdarno

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Distinctive stone cottages, equipped with every comfort, in an extraordinarily scenic location. Located in Valdarno, in front of the Chianti hills, between Florence and Arezzo is only half an hour from Siena. Due to its location, is an excellent starting point to visit  …see more

from £117 / night

£815 / week

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from £117 / night

(1) Excellent 

30

Arezzo / Antria

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £73 / night

£505 - £1107 / week

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from £73 / night

(3) Very Good 

24

Gargoyle di Sotto - Casa Nonna - Chiusi della Verna apartment sleeps 2

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
The idyllic hamlet of “Doccione di Sotto” which consists of three former farm houses, is located in a quite remote area of the Tuscan mountains. We carefully restored our old stone cottages. To the houses belong two large lawns with a pool (9x6m) for swimming, pla  …see more

from £50 / night

£319 - £423 / week

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from £50 / night

(11) Excellent 

35

Villa Nobile is a stunning 19th Century Villa - Cortona villa sleeps 24

Province of Arezzo / Cortona

7 24 3 nights min

  • 7 bedrooms
  • Sleeps 24
  • 3 nights min
  • Nearest beach 250 km
  • Swimming pool
  • Child friendly
Villa Nobile is a stunning 19th Century classical style villa recently restored authentically and with artistic charm, with a private pool 13 m x 6 m. Sitting in 4 acres of natural Tuscan rural land. A private avenue of young cypresses bringing you to our doorstep. Tran  …see more

from £65 / night

£475 / week

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from £65 / night

(2) Very Good 

23

Farmhouse 3 bedrooms, with pool & view - Loro Ciuffenna farmhouse sleeps 8

Province of Arezzo / Loro Ciuffenna

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Querceto is an historic farmhouse that sits nestled into the hillside slopes of Pratomagno mountains, among olive groves and wooks, and enjoys majestic, breathtaking views over the whole Valdarno valley, far up to the first Chianti hills. It is just 50' from Flore  …see more

from £149 / night

£623 - £1164 / week

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from £149 / 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

£742 - £1294 / week

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from £107 / 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

(9) Excellent 

18

Province of Arezzo / Cortona

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
  • Car not necessary

 …see more

from £61 / night

£397 - £432 / week

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from £61 / night

20

Country House in Toscana - Pergine Valdarno - Pergine Valdarno farmhouse sleeps 8

Province of Arezzo / Pergine Valdarno

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
It's a countryhouse built in 19th century called "Podere La Vignaccia".The house, on two floors, has been recently restored and has all the comforts.At the groundfloor there's a double sitting room with a fireplace, a big kitchenroom with kitchenett  …see more

from £173 / night

£906 - £1388 / week

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from £173 / night

Top Destination reviews

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
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
Luxury villa with private swimming pool
AMAZING!!!

I've had the most wonderful stay in this Tuscan gem! Jacopo is such a great host and was always there to answer my questions. The villa is just beautiful! Each room and corner has something unique about it. The gardner Giancarlo came to make sure the … 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
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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