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

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Villas San Gimignano
429 properties
Apartments Siena
387 properties
Apartment rentals Montepulciano
285 properties
Castelnuovo Berardenga
213 properties
Gaiole in Chianti
187 properties
Poggibonsi
172 properties
Casole d'Elsa
171 properties
Estates Montalcino
167 properties
Castellina In Chianti
159 properties
Sinalunga
156 properties
Colle di Val d'Elsa
149 properties
Pienza
148 properties
Rapolano Terme
124 properties
Asciano
116 properties
San Casciano dei Bagni
86 properties
Buonconvento
81 properties
Monteriggioni
81 properties
Cetona
72 properties
Radda in Chianti
70 properties
Sovicille
63 properties

Province of Siena

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5,381 Vacation rentals

(11) Excellent 

33

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
CasaMontepulciano is a flat of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master bedroom but in the other room i …see more

from $112 / night

$645 - $783 / week

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Responds fast!
avg. 3 hours 32 minutes

from $112 / 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 $372 / night

$2,478 - $2,974 / week

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from $372 / night

(1) Very Good 

13

Vacation apartment with shared pool in Pievescola

Province of Siena / Pievescola

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
One room apartment, very bright and with breathtaking views over the Tuscan countryside. Comfortable and functional, it is situated on the ground floor with private entrance and outdoor porch furnished for dining and enjoying the quiet and the spectacle of nature. Set …see more

from $75 / night

$496 / week

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from $75 / night

(1) Excellent 

20

Vacation home in Monticchiello

Pienza / Monticchiello

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
The "Noble" apartment (so called because it overlooks Montepulciano) Consists of: kitchen with large living room, three double bedrooms each with en suite shower. From the large windows you can admire Montepulciano, home of the noble wine, and the woods of oak and chest …see more

from $273 / night

$1,718 / week

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from $273 / night

7

Vacation apartment in San Rocco a Pilli

Sovicille / San Rocco a Pilli

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Imagine a typical Tuscan farmhouse, rustic style softened by the color of the flowers and the warmth of the furnishings, nestled in the greenery and quiet a few kilometers from the center of Siena: you are imagining our House "Podere Cappella." Built in different eras, …see more

from $199 / night

$1,388 / week

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from $199 / night

(3) Excellent 

30

Vacation farmhouse in Castiglione D'Orcia

Province of Siena / Castiglione D'Orcia

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Pet friendly
The farm Le Rogheta, 1 km from the village of Campiglia D'Orcia, in the province of Siena, is in a hilly location and overlooks a large and beautiful landscape. We are in-Artistic Natural and Cultural Park of Val d'Orcia, which was declared in 2004 by UNESCO World Herit …see more

from $81 / night

$564 - $781 / week

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from $81 / night

(3) Excellent 

13

Vacation apartment in Rapolano Terme

Province of Siena / Rapolano Terme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden
L'appartamento nasce dalla ristrutturazione di un ovile al piano terra, ha spesse e antiche mura, cucina attrezzata e luminosa con porta a vetri sul giardino, una zona armadi antistante il bagno, molto curato, un ampio salone con camino e seconda porta sull'esterno e gr …see more

from $57 / night

$63 / week

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from $57 / night

(7) Very Good 

15

Vacation apartment in Siena

Province of Siena / Siena

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Apartment on two floors situated in the Centre of Siena, St. Francis Basilica area. Excellent for visiting the numerous churches of the city, rich in history and culture; accommodation in the days of the Palio di Siena, the event more attractive to visitors. For individ …see more

from $73 / night

$496 - $808 / week

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Responds fast!
avg. 2 hours 34 minutes

from $73 / night

5

Vacation home in San Gimignano

Province of Siena / San Gimignano

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Rustic apartment in the green of the countryside for lovers of green and nature. Located on the ground floor has been renovated with handmade pieces respecting the characteristics of the house. E 'consists of a large living room with fireplace, double bedroom, bathroom, …see more

from $94 / night

$487 - $749 / week

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from $94 / night

17

Vacation apartment in Castel San Gimignano

San Gimignano / Castel San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 mi
  • Child friendly
The apartment (max 4 people) located on a beautiful hill overlooking San Gimignano, is situated in Castel San Gimignano at 375 m above sea level. The village of 400 inhabitants, offers a restaurant, a grocery store and tranquility. From there you can quickly reach the …see more

from $55 / night

$367 / week

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from $55 / night

(3) Excellent 

16

Townhouse rental in Casole d'Elsa

Province of Siena / Casole d'Elsa

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 80 mi
  • Child friendly
the apartment, which is about a mile. from casole d'Elsa. one of the most beautiful towns of Tuscany, and consists of two bedrooms, one double and one a little smaller, a cooking room, ...a nice bathroom with shower and washing machine.separate entrance with terrace, wh …see more

from $56 / night

$391 / week

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from $56 / night

21

San Gimignano Vacation farmhouse rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Originally the stable of the farm it has been restored according to the most modern standards and comfortably furnished. Ideal for 4 people. The entrance is through the spacious kitchen, equipped with a fireplace. There are 2 bedrooms and a modern bathroom. The kitche …see more

from $124 / night

$868 / week

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from $124 / night

(2) Very Good 

10

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Our apartments are located in the northern part of the country to 150 meters from the walls of the old town, in a very quiet area, where you can easily find place for the machine without having to pay. In about 5 minutes on foot you can reach the historic center. The ap …see more

from $81 / night

$564 / week

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Responds fast!
avg. 2 hours 33 minutes

from $81 / night

11

Vacation apartment in Torrita di Siena

Province of Siena / Torrita di Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
This beautiful holiday home is located at 200 mt from the pretty medieval village of Torrita di Siena, only 15 km from Pienza and Montepulciano, in the heart of Val di Chiana, an attractive valley in the south-east of the region. The farmhouse faces on a side the villag …see more

from $90 / night

$298 - $626 / week

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avg. 1 hour 53 minutes

from $90 / 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 $192 / night

$1,091 - $3,073 / week

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from $192 / night

19

Castiglione D'Orcia Vacation home rental

Province of Siena / Castiglione D'Orcia

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Villa is part of a hamlet settled on top of a hill in the Orcia valley. It is just at 2,5km from the village Cartiglion d'Orcia and just about 10 km far from Monte Amiata. The villa has a wide private garden and a stunning vieux over the countryside of Val d'Orcia …see more

from $206 / night

$583 - $1,236 / week

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Responds fast!
avg. 3 hours 54 minutes

from $206 / night

(11) Excellent 

Certificate of Excellence

10

Vacation townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly
Agriturismo, within the organic farm, located in San Giusto a Balli in the heart of Montagnola Senese, hilly area west of the city of Siena in Tuscany, wooded and full of sources, and for its natural historical and artistic peculiarities is a site of Community interest. …see more

Certificate of Excellence

from $137 / night

$954 / week

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from $137 / night

23

Vacation farmhouse with shared pool in Radicofani

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
It is located in Radicofani in the heart of the Val d'Orcia (Siena), in a landscape of remarkable impact, declared "World Heritage of Humanity" by UNESCO. The property was recently renovated by recovering the original materials, while maintaining the typical traditions …see more

from $124 / night

$868 / week

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from $124 / night

12

Vacation farmhouse in Montepulciano

Province of Siena / Montepulciano

4 7 1 night min

  • 4 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
Sunflower B&B is situated on a hill, along the road to Pienza a few hundred meters from the Temple of San Biagio and the cross-roads for Chianciano Terme. Enjoys a panoramic position, only in the area, allowing more than the sight of Montepulciano and Montefollonico tha …see more

from $310 / night

$1,611 / week

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from $310 / night

6

Vacation home in Vescovado di Murlo

Murlo / Vescovado di Murlo

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Private garden
CASINA INDEPENDENT, SITA ON THE EDGE OF THE VILLAGE OF MURLO VESCOVADO, SURROUNDED BY TUSCAN COUNTRY, IN POSITION OVERVIEW AND QUIET. Il Piccolo GARDEN, EQUIPPED WITH TABLE AND CHAIRS, NICE PARKS PERMITS FOR MEALS AND / OR OTHER ACTIVITIES 'OUTDOORS. THE HOUSE AND 'ARRA …see more

from $73 / night

$496 - $645 / week

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from $73 / night

(7) Excellent 

23

Vacation apartment in Pienza

Province of Siena / Pienza

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Child friendly
  • Air conditioning
New lower price - one of the nicest flat in Tuscany 5 star standard !! The apartment has its own entrance and occupies the whole 1st and top floors of this classical building next to the ancient city wall. Private parking, large roof terrace (55m2) with g …see more

from $186 / night

$1,301 / week

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from $186 / night

(2) Excellent 

26

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The palazzo dei Diavoli is a small holiday structure composed of 1) an apartment-independent SORBIAN House, with 2 bedrooms, 2 bathrooms, a fully equipped kitchen, terrace and independent equipped garden, air conditioning inside, suitable for small families or 2 couples …see more

from $149 / night

$868 / week

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from $149 / night

(1) Excellent 

19

Villa rental in San Casciano dei Bagni with swimming pool

Province of Siena / San Casciano dei Bagni

7 15 1 night min

  • 7 bedrooms
  • Sleeps 15
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Podere Tina is located on a hilltop in the extreme north of the province of Lazio, bordering on Tuscany and close to Umbria. The hilltop where the former farmhouse, the stables and the swimming pool are located offers a glorious panoramic view of the undulating historic …see more

from $892 / night

$6,319 / week

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from $892 / night

(8) Very Good 

20

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Casa Gigliola, holiday villa near Siena, can accommodate up to 7 people and is perfect for a large family or a group of friends, has private parking space, a large balcony and easy access to the village swimming pool. The house is located in Monticiano, a medieval v …see more

from $100 / night

$694 / week

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Responds fast!
avg. 3 hours 12 minutes

from $100 / night

(2) Good 

12

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
, The plant L'Aquila can accommodate 30 people and has six apartments, a studio and three double bedrooms, each with bath, shower and toilet. Fireplaces in some of the apartments and the rustic spread a cozy atmosphere with a good dose of atmosphere. All apartments and …see more

from $106 / night

$737 / week

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from $106 / night

(5) Excellent 

21

Tower rental in Monticchiello

Pienza / Monticchiello

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Ask about children
  • Private garden
In Val d'Orcia, Monticchiello di Pienza is a small medieval town, surrounded by walls and protected by four towers; one of these is ' Charles ' Tower, which stands at the highest point of the village and has a panoramic view across the Valley. Sunsets and beautiful wil …see more

from $188 / night

$999 / week

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from $188 / night

(5) Excellent 

24

Barn rental in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
Our 'hut' well restored is located in the middle of the beautiful hills of Chianti, in a quiet environment close to the places of art of Tuscany. It houses four / five people in two bedrooms upstairs, a bathroom in the mid-scale and large living room with fully equipped …see more

from $118 / night

$824 - $1,041 / week

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from $118 / night

30

San Gusme Vacation villa rental

Castelnuovo Berardenga / San Gusme

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn. The large private garden is totally fenced ensuring …see more

from $217 / night

$1,518 - $2,094 / week

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from $217 / night

13

Vacation apartment with shared pool in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Ancient Tuscan farmhouse of 1800 a short walk from the medieval center of San Quirico d'Orcia and only 100 meters from the supermarket, the bar-cafeteria and bus stop. Sarna offers the possibility of a stay made of silences and quiet passage of time, the atmosphere rela …see more

from $81 / night

$539 - $787 / week

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from $81 / night

18

Apartment rental in Monticiano

Province of Siena / Monticiano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Entrance Kitchen with dining area Bathroom Living room Master bedroom Monticiano is a typical ancient Tuscany village, 7 Km away from Terme di Petriolo, an old thermal town with hot spring facilities open all the year . Situated at 35km from Siena and Grosseto, this ti …see more

from $87 / night

$496 / week

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from $87 / night

25

Apartment rental in Castellina In Chianti

Province of Siena / Castellina In Chianti

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Private garden
Lovely apartment of 40 square meters. Carefully renovated according to the ancient Tuscan traditions. This is one of the two apartments which make up the old barn. Nestled in the heart of Chianti Classico, well studied in details, comfortable and suitable for singles …see more

from $69 / night

$477 / week

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from $69 / night

(2) Very Good 

28

Vacation apartment with shared pool in Ulignano

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
The ONE is the premium apartment of our Montegonfoli Farmhouse. What makes this apartment special and all the property is its position, on the highest hill of the surroundings, that provides wonderful views at 360°, including San Gimignano towers and Tuscany hills. The …see more

from $149 / night

$868 - $1,363 / week

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Responds fast!
avg. 2 hours 52 minutes

from $149 / 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 $81 / night

$533 - $979 / week

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Responds fast!
avg. 1 hour 48 minutes

from $81 / night

(1) Excellent 

16

Apartment rental in Casole d'Elsa with shared pool

Province of Siena / Casole d'Elsa

1 7 3 nights min

  • 1 bedroom
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Apt with terrace and large shared pool in an ancient borgo nestled in the countryside between Siena, San Gimignano and Volterra. It hosts 4 people comfortably, has 7 beds. Large living room with kitchen corner and a loft, master bedroom and bathroom with shower. It ha …see more

from $86 / night

$521 - $738 / week

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Responds fast!
avg. 41 minutes

from $86 / night

(13) Excellent 

20

Vacation apartment with golf nearby in Sant'Angelo in Colle

Montalcino / Sant'Angelo in Colle

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 68 mi
  • Suitable for children age 5+
  • Private garden
Minnie's Cottage is a Tuscan house built with love. We are in Sant'Angelo in Colle, in the municipality of Montalcino from which we are only 10 km away. It's a beautiful country situated on a hill surrounded by endless acres of vineyards in Brunello wine and beautiful c …see more

from $93 / night

$558 - $1,078 / week

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from $93 / night

(7) Excellent 

Certificate of Excellence

36

Vacation villa with indoor pool in Radicondoli

Province of Siena / Radicondoli

4 9 5 nights min

  • 4 bedrooms
  • Sleeps 9
  • 5 nights min
  • Nearest beach 79 mi
  • Swimming pool
  • Child friendly
Set in the heart of Tuscany this spacious, detached, hilltop villa has 180° views from a grand terrace and is close to Siena, the beach and all the other important sights. Enjoy fantastic indoor and outdoor spaces. Every room has a view of Tuscany as it unfolds beneath …see more

Certificate of Excellence

from $434 / night

$3,098 - $3,717 / week

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Responds fast!
avg. 1 hour 51 minutes

from $434 / night

(1) Excellent 

16

Casole d'Elsa Vacation townhouse rental

Province of Siena / Casole d'Elsa

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Ripostena is a family run holiday house situated in the heart of Montagnola Senese, an area of great naturalistic value.Its strategic location makes it easy to reach Siena, San Gimignano, Florence and the Chianti hills. The ancient village was entirely restored rural Tu …see more

from $143 / night

$770 / week

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from $143 / night

55

Vacation farmhouse in Cetona

Province of Siena / Cetona

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Do you need relaxation and energy in your life? Is it lovely for you to true green holiday in the tuscan picture? Know our little country house: The Caio is an old farm in the medieval tower house, preserving all the charm of the old structure and traditional furnishing …see more

from $149 / night

$868 / week

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from $149 / night

12

Vacation apartment in San Quirico d'Orcia

Province of Siena / San Quirico d'Orcia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
ancient Tuscan farmhouse of 1800 a short walk from the medieval center of San Quirico d'Orcia and only 100 meters from the supermarket, the bar-cafeteria and from the bus stop, the Sarna offers the possibility of a stay made of silences and peaceful flow of the time, th …see more

from $97 / night

$663 - $961 / week

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from $97 / night

11

Monteriggioni Vacation villa rental

Province of Siena / Monteriggioni

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa near Monteriggioni : Located in the heart of Tuscany, to the south of Florence, Villa Gianni is an attractive small  property, recently renovated and well furnished throughout. Located in wine country, there are classic Tuscan views from around the property of vin …see more

from $320 / night

$2,240 - $3,542 / week

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from $320 / night