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

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Villas San Gimignano
452 properties
Apartments Siena
380 properties
Apartment rentals Montepulciano
306 properties
Castelnuovo Berardenga
247 properties
Gaiole in Chianti
208 properties
Poggibonsi
193 properties
Casole d'Elsa
166 properties
Sinalunga
162 properties
Estates Montalcino
160 properties
Castellina In Chianti
153 properties
Colle di Val d'Elsa
147 properties
Pienza
142 properties
Rapolano Terme
140 properties
Asciano
115 properties
Chiusi
87 properties
San Casciano dei Bagni
87 properties
Monteriggioni
79 properties
Cetona
73 properties
Chianciano Terme
70 properties
Sovicille
67 properties

Province of Siena

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5,894 Vacation rentals

(7) 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 San …see more

from $69 / night

$479 - $1,413 / week

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avg. 2 hours 33 minutes

from $69 / night

(1) Excellent 

22

Siena Vacation apartment rental

Province of Siena / Siena

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 80 mi
  • Child friendly
  • Car not necessary
Prestigious house in the medieval heart of Siena. A beautiful house in the center of Siena, where to be pampered in the beauty of a unique city. Step into a historical building in Siena - a short walk from Piazza del Campo - and treat yourself to your holiday in a charm …see more

from $221 / night

$1,548 / week

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Responds fast!
avg. 2 hours 55 minutes

from $221 / night

44

Vacation villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 5 BA Villa dates back to the 15th century and is strategically located with a short distance from the lively village of Castellina in Chianti. Surrounded by an exceptionally beautiful landsc …see more

from $684 / night

$4,790 - $7,307 / week

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from $684 / night

(1) Excellent 

49

Siena Vacation villa rental

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
This beautiful villa in Siena with Pool&SPA and air conditioning is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beauti …see more

from $430 / night

$2,764 - $5,220 / week

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from $430 / night

(4) Excellent 

39

Vacation villa with swimming pool in Siena

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room …see more

from $191 / night

$1,081 - $2,837 / week

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from $191 / night

(5) 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 Gimignan …see more

from $69 / night

$479 - $1,413 / week

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avg. 2 hours 33 minutes

from $69 / night

(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 farmers o …see more

from $185 / night

$1,228 - $2,825 / week

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avg. 1 hour 12 minutes

from $185 / night

(14) Excellent 

Certificate of Excellence

25

Vacation farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere …see more

Certificate of Excellence

from $121 / night

$811 - $1,413 / week

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Responds fast!
avg. 2 hours 35 minutes

from $121 / night

15

Val d'Orcia Vacation apartment rental

Montalcino / Val d'Orcia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 mi
Bacchus ' apartment mq. 60.00 (1376891 2-picture 3-4) is composed exclusively of:-entrance kitchen, bedroom with double bed, bathroom with shower and central heating. All rooms have panoramic views. The cottage used for farm is made of Tuff stone dating from about 180 …see more

from $123 / night

$860 / week

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from $123 / night

22

Vacation farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Podere Vesta is a small hamlet consisting of 4 adjacent buildings, where are located the apartments and common areas. For nature lovers, look out every window offers an incomparable view, by the landscapes of the Val d'Orcia, the Crete Senesi glimpse of Siena to the vie …see more

from $155 / night

$576 / week

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avg. 3 hours 12 minutes

from $155 / night

(30) Excellent 

Certificate of Excellence

18

Vacation apartment in Siena

Province of Siena / Siena

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
Historic Residence Palazzo Bichi Ruspoli is situated on the main street, in the heart of Siena. The entrance is from the ancient tower, one of the three buildings wich the palace is composed. The house is on the third floor with elevator and has a stunning view on the c …see more

Certificate of Excellence

from $147 / night

$1,007 - $2,911 / week

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Responds fast!
avg. 3 hours 9 minutes

from $147 / night

(1) Excellent 

24

Vacation apartment in Val di Merse

Siena / Val di Merse

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Child friendly
The antique spaces have been reinvigorated, made more comfortable and personalized whilst using traditional local materials, rough stone, terra cotta, wrought iron, wood. There are six complete and elegant, well-appointed apartments, complete with stylish fitted bathroo …see more

from $369 / night

$2,457 - $2,948 / week

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avg. 2 hours 49 minutes

from $369 / night

(10) Excellent 

Certificate of Excellence

37

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
The apartment Tino is 55 Square meters and accommodates up to 4 people. First floor is composed of sitting/dining room with cooking area (dishwasher) and fireplace, 2 bedrooms, 1 bathroom with shower. sofabed for one people in living room for a child. In the garden , …see more

Certificate of Excellence

from $62 / night

$430 / week

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Responds fast!
avg. 3 hours 20 minutes

from $62 / night

(2) Excellent 

14

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Ask about pets
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of this vi …see more

from $74 / night

$492 / week

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from $74 / night

(1) Excellent 

20

Vacation farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere …see more

from $99 / night

$676 - $1,290 / week

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Responds fast!
avg. 2 hours 35 minutes

from $99 / night

(50) Excellent 

Certificate of Excellence

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, tastefully r …see more

Certificate of Excellence

from $126 / night

$875 - $1,260 / week

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from $126 / night

(2) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
The Casale is a very nice private villa, reachable through a dirt road easy to go also with a city car! The villa has a private swimming pool, outdoor BBQ and Jacuzzi, 5 bedrooms and 5 bathrooms (at least 10 people), it also has a big kitchen a big living room with fire …see more

from $492 / night

$3,439 - $3,807 / week

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from $492 / night

14

Ski home to rent in Abbadia San Salvatore

Province of Siena / Abbadia San Salvatore

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly
Cozy farmhouse in the Tuscan countryside, "brings South" of the Val d'Orcia, at the foot of Monte Amiata. For 6 pers. (+2 possible), equipped kitchen, large courtyard for exclusive use. A privileged to visit Siena and northern Lazio. Lagaccione is a stone country house, …see more

from $123 / night

$860 / week

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from $123 / night

(3) Very Good 

15

Vacation home in Bagni di San Filippo

Province of Siena / Bagni di San Filippo

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
The Thermae apartment on the first floor of a recently renovated house has a private entrance with a small courtyard covered. It consists of a living room with sofa bed, dining table and fireplace. A small kitchen, a bedroom with double bed and bathroom with shower. The …see more

from $79 / night

$403 / week

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avg. 3 hours 5 minutes

from $79 / night

(12) Excellent 

65

Vacation villa in San Giovanni d'Asso

Montalcino / San Giovanni d'Asso

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
You could not ask for a more special place in which to celebrate an important anniversary or simply spend a vacation with your family and friends ! I Melograni is a beautiful antique,indipendent, "casale" with a large fenced swimming pool (5x12 mt), 1km away (walking …see more

from $653 / night

$4,569 - $6,190 / week

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avg. 3 hours 9 minutes

from $653 / night

(3) Very Good 

20

Radicondoli Vacation apartment rental

Province of Siena / Radicondoli

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
The apartment La Ginestra is situated on the ground floor of the Villa Il bel canto. It has: a large dining/sitting room with kitchen corner, chimney, tv, and a large window door to the garden. In the winter floor heating in every room.The kitchen is fully organized wit …see more

from $111 / night

$774 - $946 / week

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from $111 / night

(6) Very Good 

23

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
This is a spacious fully furnished 2 bedroom apartment in Borgo di Gaiole in the village of Gaiole in Chianti. Gaiole is in the heart of the Chianti Classico Region of Tuscany.The property has stunning views over the village and to the vineyards overlooking the village …see more

from $210 / night

$840 / week

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avg. 2 hours 49 minutes

from $210 / night

31

Asciano Vacation villa rental

Province of Siena / Asciano

5 9 3 nights min

  • 5 bedrooms
  • Sleeps 9
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
As guests enter the property there is an entrance hall leading off to a living area on the right and large kitchen on the left. This area has an open plan feel to it. The kitchen is superbly equipped with everything guests could possibly need and want during their stay. …see more

from $430 / night

$2,395 - $5,158 / week

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Responds fast!
avg. 3 hours 15 minutes

from $430 / night

(6) Excellent 

21

Villa rental in Montisi with swimming pool

Province of Siena / Montisi

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
'Casa Valerio' is a luxury 16th century village house, so named in memory of the much loved local ironmonger, Valerio Manzi, whose family occupied this tall stone village house for generations. It sits right in the centre of the beautiful medieval hilltop village of Mon …see more

from $336 / night

$2,100 - $3,290 / week

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from $336 / night

13

Chiusdino Vacation villa rental

Province of Siena / Chiusdino

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 35 mi
  • Child friendly
  • Pet friendly
Case Vacanze Chiusdino Appartamenti Vacanze a Chiusdino Il comune di Chiusdino, paese natale di San Galgano, dista circa 40 chilometri da Siena ed è immerso nella natura incontaminata della Val di Merse regione d'Italia. Chiusdino è un ottimo punto di partenza per espl …see more

from $148 / night

$1,032 / week

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from $148 / night

(1) Excellent 

21

Campiglia d'Orcia Vacation home rental

Province of Siena / Campiglia d'Orcia

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
We are located in the historic center of this ancient village. The house makes use of a large living area, a very large area and a relaxation area with fireplace English. On the same floor, a double bedroom, bathroom, utility room with washing machine and second bathroo …see more

from $93 / night

$614 - $1,388 / week

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from $93 / night

(12) Excellent 

27

San Gimignano Vacation farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Less than 1km away from the Via Francigena, La Proda is part of a little rural hamlet, whose ancient nucleus dates back to the Middle Ages. The area's toponym “Strada” attests to these places' historical value. Carefully restored, surrounded by centuries-old cypresses a …see more

from $178 / night

$1,044 - $1,450 / week

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avg. 2 hours 8 minutes

from $178 / night

25

Pienza Vacation lodge rental

Province of Siena / Pienza

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Air conditioning
Poggio ai Gelsi is located in the south of Tuscany between the hills of Val d'Orcia, Siena and halfway between Montepulciano and Pienza. The property enjoys a magnificent view over Montichiello and Pienza. The colours of the nature in this corner of Tuscany are beautifu …see more

from $120 / night

$834 - $1,290 / week

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from $120 / night

29

Siena Vacation home rental

Province of Siena / Siena

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
House (120 m2) in an elegant Residence in typical Tuscan style, with nice pool attached. Entrance and terrace with loggia and garden independent. The nearest village is Villa a Sesta (600 meters, even walkable) with two restaurants and a bar. At 7 km there's the town of …see more

from $121 / night

$848 - $1,413 / week

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from $121 / night

(14) Excellent 

Certificate of Excellence

34

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 120 mi
  • Child friendly
  • Air conditioning
The house is located about 1.5 kilometers from the historic center of Montepulciano, in the tranquility and silence of the Tuscan countryside. House for exclusive use. The property was recently renovated in rustic style on the outside there is a beautiful garden. The ce …see more

Certificate of Excellence

from $99 / night

$737 - $971 / week

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from $99 / night

(5) Excellent 

18

Apartment rental in Siena with shared pool

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 mi
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will …see more

from $111 / night

$737 - $1,351 / week

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from $111 / night

(1) Excellent 

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 $74 / night

$498 - $989 / week

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Responds fast!
avg. 2 hours 9 minutes

from $74 / night

(24) Excellent 

Certificate of Excellence

43

Vacation apartment in Monticchiello

Pienza / Monticchiello

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • 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 Classico …see more

Certificate of Excellence

from $93 / night

$645 / week

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from $93 / night

23

Vacation home in Piancastagnaio

Province of Siena / Piancastagnaio

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
The house San Giuseppe, a few kilometers from the Val D'Orcia, is the place you were looking to relax and unwind from the hustle and bustle of today. St. Joseph is divided into six detached houses restored according to the Tuscan aesthetic. The swimming pool and barbecu …see more

from $134 / night

$937 / week

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from $134 / night

(6) Excellent 

Certificate of Excellence

48

Vacation cottage in Castellina In Chianti

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 mi
  • Child friendly
  • Private garden
Traditional, independent house in peaceful countryside in the heart of Chianti La Capanna delle Cozzole is located close to Castellina in Chianti, only a 30 minute drive from Siena, Florence and San Gimignano. It is set perfectly in the lush countryside between ancient …see more

Certificate of Excellence

from $148 / night

$688 - $811 / week

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Responds fast!
avg. 3 hours 17 minutes

from $148 / night

(1) Excellent 

18

Vacation apartment rental

Province of Siena / Montepulciano

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
90 sqm apartment with wide living room and fireplace. The House is rustic with wooden table and straw chairs (see photo) has two large rooms and a smaller apartment is located on the ground floor, directly on the garden, so easily accessible, overlooking the countryside …see more

from $74 / night

$504 - $934 / week

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Responds fast!
avg. 1 hour 48 minutes

from $74 / night

(28) Excellent 

42

Vacation apartment in Montisi

Province of Siena / Montisi

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 150 mi
  • Suitable for children age 5+
A one-bedroom romantic apartment in a charming Medieval village in Tuscany. The village is off the beaten track and yet very close to the world known countryside of Tuscany and its most important art cities and wine districts. Pienza and Montepulciano are only 20 minute …see more

from $148 / night

$983 / week

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from $148 / night

(33) Excellent 

25

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 at ju …see more

from $99 / night

$614 - $835 / week

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Responds fast!
avg. 2 hours 4 minutes

from $99 / night

11

Radicofani Vacation apartment rental

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Agriturismo podere san giorgio consists of 5 apartments, furnished to employees Tuscan style with fireplace, sat tv, wi-fi, a large garden with swimming pool. Located in the parco della Val D'orcia one can visit many medieval towns like Pienza, Montepulciano, San Quiric …see more

from $105 / night

$731 / week

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from $105 / night

(7) Excellent 

Certificate of Excellence

30

Vacation guest house in Siena

Province of Siena / Siena

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
★My Cozy Country House is part of a hamlet about 20km from Siena and central to Chianti, San Gimignano, Florence, Montalcino&Montepulciano. It's located in a forest on top of a hill in the heart of Tuscany. Peaceful and quiet area. Patio&Garden. Perfect for hiking&bikin …see more

Certificate of Excellence

from $74 / night

$492 - $725 / week

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Responds fast!
avg. 2 hours 28 minutes

from $74 / night