50 Best Vacation Rentals in Province of Siena - Holiday Lettings - Cabins

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Villas San Gimignano
451 properties
Apartments Siena
437 properties
Apartment rentals Montepulciano
273 properties
Casole d'Elsa
212 properties
Colle di Val d'Elsa
195 properties
Castelnuovo Berardenga
169 properties
Poggibonsi
166 properties
Castellina In Chianti
157 properties
Estates Montalcino
149 properties
Pienza
148 properties
Sinalunga
145 properties
Gaiole in Chianti
132 properties
Rapolano Terme
132 properties
Asciano
124 properties
Buonconvento
84 properties
Cetona
82 properties
Radda in Chianti
81 properties
Monteriggioni
80 properties
Radicondoli
77 properties
San Casciano dei Bagni
73 properties

Province of Siena

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4,034 Vacation rentals

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(5) Excellent 

21

Vacation villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from $159 / night

$1060 - $2438 / week

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from $159 / night

(18) Excellent 

43

Vacation apartment in Monticchiello

Pienza / Monticchiello

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Villa PoliFlora is a modern residence in Monticchiello in Val d'Orcia, a Unesco world heritage site. The owners and creators invite you for a relaxing stay, in the triangle among Montalcino, Pienza and Montepulciano. A few kilometers away from Siena and Chianti Cla  …see more

from $80 / night

$393 - $956 / week

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from $80 / night

(42) Excellent 

19

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from $240 / night

$1300 - $1900 / week

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from $240 / night

Featured properties

(12) Excellent 

69

Vacation villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
VILLA LISIDOR: FULLY RENOVATED WITH ALL NEW AMENITIES. The habitable area is doubled: from 150 square meters to 300 square meters. On GROUND FLOOR, which is at garden level, is a large sitting room with Tv Sat area, a dining room in front of the pool, a professional  …see more

from $502 / night

$3514 - $5406 / week

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from $502 / night

(46) Excellent 

25

Vacation home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, ta  …see more

from $112 / night

$775 - $1116 / week

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from $112 / night

110

Siena Vacation villa rental

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Villa Nuti is an elegant XVII century manor only 3 km from the center of Siena, the bus stop to the centre is 400 meters from the villa. From its unique terrace it enjoys privileged magnificent views of the town with its famous bell towers. The villa has been completel  …see more

from $455 / night

$3180 - $4187 / week

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from $455 / night

(48) Excellent 

21

Vacation cottage in Montepulciano

Province of Siena / Montepulciano

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 158 mi
  • Child friendly
  • Air conditioning
Placed in the countryside of Montepulciano, near the most important historical towns such as Pienza, Montalcino and Bagno Vignoni, the Casina Toscana is a historical residence of the nineteenth century, which allows guests to enjoy the tranquility and relaxation that th  …see more

from $75 / night

$424 - $742 / week

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from $75 / night

35

Vacation villa rental

Province of Siena / Ville di Corsano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly
The large 800 sqm villa is an ancient historical residence. Villa Siena, an 18th century villa, rises within a se cluded parkland in the hills of Tuscany. The theme of the outdoors continues in the elegant drawing room, formerly a ballroom, whose vaulted ceiling and wal  …see more

from $720 / night

$5035 - $7684 / week

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from $720 / night

22

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $114 / night

$498 - $1358 / week

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from $114 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gim  …see more

from $43 / night

$297 - $1018 / week

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from $43 / night

(30) Excellent 

20

Vacation apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 50 mi
  • Child friendly
  • Pet friendly
The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking  …see more

from $85 / night

$509 - $711 / week

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from $85 / night

(3) Very Good 

35

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $112 / night

$779 / week

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from $112 / night

(2) Excellent 

16

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
nice and comfortable apartment in the old town of Montepulciano Placed in the Historical Centre, just a few steps to the most beautiful and oldest wine cellar in Montepulciano (Cantina del Redi dè Ricci) an amazing sixteenth-century structure, great-looking wit  …see more

from $80 / night

$477 / week

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from $80 / night

(11) Excellent 

21

Gracciano Vacation cottage rental

Montepulciano / Gracciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The cottage is opposite the owner's house and consists of two double bedrooms, two bathrooms and a large living room with cooking area. The living area opens onto a patio and pergola and the downstairs bedroom also opens onto a small patio. There is access for the  …see more

from $85 / night

$467 - $2184 / week

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from $85 / night

(6) Excellent 

128

Vacation villa with swimming pool in Cetona

Province of Siena / Cetona

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Chieteno, a splendid property of about 500 square metres built on two levels with a tower comprising the third, is located near the attractive medieval village of Cetona, just an hour's drive from important centres such as Florence, Arezzo, Perugia, Assisi an  …see more

from $795 / night

$3180 - $5266 / week

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from $795 / night

21

Vacation apartment in Siena

Province of Siena / Siena

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Car not necessary
This is my holiday home in Siena, my home town. I have tried to tell you everything you need to know in my description, but please do not hesitate to ask me questions before booking - I am fluent in English, French and Italian. The flat is on the ground floor, on the  …see more

from $128 / night

$891 / week

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from $128 / night

(1) Very Good 

23

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $128 / night

$742 - $1166 / week

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from $128 / night

(3) Excellent 

35

Vacation farmhouse in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 120 mi
  • Child friendly
Farmholiday Agriturismo Podere Tegline is of a family from the Chianti region for many centuries, and always produce Chianti Classico wine and extra virgin olive oil organic. We restored the farmhouse of the 15th century and Giovanni has personally followed all the wor  …see more

from $109 / night

$689 - $742 / week

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from $109 / night

(6) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we underst  …see more

from $106 / night

$636 / week

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from $106 / night

7

Province of Siena / Siena

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Ask about pets

 …see more

from $85 / night

$583 - $880 / week

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from $85 / night

(2) Excellent 

63

Villa rental in Montepulciano with swimming pool

Province of Siena / Montepulciano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
Villa Bossona is an impressive villa which dates back to the eighteenth century. Ideal for quiet and relaxing holidays it is located in the sweet Montepulciano hills few minutes from the town. A small church with an enchanting bell tower is preserved in its original for  …see more

from $636 / night

$4134 - $4558 / week

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from $636 / night

(6) Very Good 

38

Vacation villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The  …see more

from $212 / night

$1135 - $2862 / week

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from $212 / night

(3) Excellent 

26

Vacation apartment with shared pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Ask about pets
Casanova di Lucignano has three apartments - Rosmarino, Lavanda and Maggiorana – all containing a bedroom, bathroom and a living room with an attached kitchen. All apartments also have a fireplace and a color TV; free Wi-fi Internet access is available for guests.  …see more

from $96 / night

$382 - $594 / week

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from $96 / night

21

Vacation b&b in Acquaviva di Montepulciano

Montepulciano / Acquaviva di Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Tenuta di Argiano a Montepulciano, located near MONTEPULCIANO, is surrounded by vineyards growing grapes for the famous local wines, Vino Nobile di Montepulciano and Rosso di Montepulciano, and is peaceful and quite. swimming pool and wifi . bikes tour, spa nearby, It  …see more

from $73 / night

$505 / week

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from $73 / night

(1) Excellent 

24

Villa rental in Castellina In Chianti with shared pool

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has  …see more

from $484 / night

$2899 - $5006 / week

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from $484 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from  …see more

from $44 / night

$308 - $1050 / week

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from $44 / night

50

Vacation apartment in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
Enjoy winelovers' paradise in Montalcino from the beautifully renovated and spacious apartment - Casa Brunello di Montalcino - in the 17th century building with some nice original pieces, combining the traditional Tuscan countryside look with modern high-quality fu  …see more

from $345 / night

$2120 - $2968 / week

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from $345 / night

(1) Excellent 

17

San Giovanni d'Asso Vacation villa rental

Province of Siena / San Giovanni d'Asso

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Italian village rental - This charming historic residence is part of a larger building, located in the village of San Giovanni d'Asso, just beyond the original castle walls and a short walk to the centre.With origins dating back to the 15th century this property ce  …see more

from $310 / night

$2170 - $3051 / week

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from $310 / night

(1) Very Good 

36

Province of Siena / Siena

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Child friendly
  • Car not necessary

 …see more

from $96 / night

$668 / week

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from $96 / night

(16) Excellent 

22

Casole d'Elsa Vacation cottage rental

Province of Siena / Casole d'Elsa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
La Casa Dei Nonni is a beautiful villa located just outside the tiny village of Monteguidi, immersed in the beautiful Tuscan countryside. The villa has a spacious living room with fireplace, a fitted kitchen with a second fireplace, a bedroom with two single beds and a  …see more

from $159 / night

$954 - $1431 / week

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from $159 / night

(11) Very Good 

32

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Nestled in a centuries-old complex of farm-house buildings, just 10 minutes drive from the medieval "skyscraper" fortress town of San Gimignano...Le Fontanelle is the perfect place to soak in Tuscany's sunshine, culture, food and fun.An easy drive fro  …see more

from $75 / night

$562 - $1002 / week

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from $75 / night

(12) Excellent 

24

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
.The apartment, Into The Sunset, owes its name to the magnificent views of the hills of Val d'Orcia which you can enjoy from its windows. It is located in the center of Montepulciano, via Collazzi 10, only 200 meters from Piazza Grande, the heart of the city, wher  …see more

from $122 / night

$742 - $920 / week

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from $122 / night

17

Vacation apartment with shared pool in Montepulciano

Province of Siena / Montepulciano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
These beautiful holiday accommodations are located in a quiet area just 7km from Montepulciano, a splendid medieval town of the Val di Chiana. Nearest village, Acquaviva, is ca. 1.5km away, where one can find shops, a supermarket and restaurants. The property consists  …see more

from $69 / night

$435 - $854 / week

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from $69 / night

16

Vacation cottage in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
The cottage is in the heart of the hamlet which is completely surrounded by ancient walls, and has a splendid view of the parish church and all the valley. It is independent and surrounded by a large garden. All the ceramics in the house were painted by the owner and ha  …see more

from $150 / night

$1050 - $1346 / week

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from $150 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room w  …see more

from $75 / night

$318 - $552 / week

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from $75 / night

(2) Excellent 

22

Pienza / Monticchiello

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $53 / night

$361 - $465 / week

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from $53 / night

(6) Very Good 

45

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from $96 / night

$583 - $615 / week

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from $96 / night

(3) Very Good 

11

Siena Vacation apartment rental

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 mi
The apartment is ideal for holiday in Siena is located in the centre of Siena, one of the most beautiful towns in Italy.The position of the flat with a splendid view on the cathedral and San Domenico church and the position in the centre of the town create a nice es  …see more

from $101 / night

$509 / week

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from $101 / night

(6) Excellent 

32

Vacation home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
In our rustic house Il Torrione you will find all the peacefulness that only Tuscany can offer the visitor. Our customers will find this large apartment in Radicondoli, town in the green of Tuscany hills, composed by three bedrooms, bathrooms, a kitchen, a living room a  …see more

from $122 / night

$848 - $1325 / week

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from $122 / night

(1) Excellent 

26

Vacation home in Rigomagno

Sinalunga / Rigomagno

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Part of an old farmhouse set on a hill overlooking the charming medieval village of Rigomagno and a large part of the Chiana Valley. In this area the hills are mostly covered with the silver-green foliage of olive trees, interspersed now and then with a small vineyard o  …see more

from $99 / night

$689 - $1580 / week

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from $99 / night