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

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Villas San Gimignano
497 properties
Apartments Siena
450 properties
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Colle di Val d'Elsa
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Casole d'Elsa
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Castelnuovo Berardenga
200 properties
Poggibonsi
171 properties
Castellina In Chianti
170 properties
Estates Montalcino
162 properties
Gaiole in Chianti
159 properties
Sinalunga
152 properties
Pienza
146 properties
Rapolano Terme
144 properties
Asciano
113 properties
Cetona
90 properties
San Casciano dei Bagni
90 properties
Radda in Chianti
87 properties
Buonconvento
80 properties
Monteriggioni
80 properties
Radicondoli
75 properties

Province of Siena

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4,296 Vacation rentals

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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 $129 / night

$898 / week

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from $129 / 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 $81 / night

$396 - $965 / week

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from $81 / night

24

Vacation villa rental

Castelnuovo Berardenga / Vagliagli

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly closed and the swimming pool, just below the house ground, has a lovely view over the valley and th  …see more

from $248 / night

$1736 - $2632 / week

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from $248 / night

Featured properties

(4) Excellent 

11

Province of Siena / Pienza

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

 …see more

Pricing unknown

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Pricing unknown

(32) Excellent 

24

Gaiole in Chianti Vacation apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from $75 / night

$521 - $825 / week

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from $75 / 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

(2) Excellent 

21

Vacation apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
"Prisca House" is a wonderful first floor apartment lovingly restored to a high standard, set as a precious stone on the heart of Buonconvento Borgo.Tastefully and comfortable furnished, this apartment has a warm and friendly atmosphere and it offers guest  …see more

from $75 / night

$524 / week

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from $75 / night

35

Radicofani / Contignano

2 5 1 night min

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

 …see more

from $81 / night

$556 - $781 / week

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from $81 / 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

(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 $86 / night

$514 - $717 / week

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from $86 / 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 $115 / night

$502 - $1370 / week

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from $115 / 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 $86 / night

$471 - $2203 / week

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from $86 / 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

$509 / week

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from $73 / night

24

Celle sul Rigo Vacation villa rental

San Casciano dei Bagni / Celle sul Rigo

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The farmhouse is located near Radicofani, under the UNESCO Patrimony (being a part of the Val d'Orcia) 4.5 km from the town centre along the old dirt Francigena Road. The ancient house, restructured with a rustic style, is part of a farm with 96 hectars of cultiva  …see more

from $233 / night

$1625 - $3071 / week

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from $233 / night

(1) Excellent 

14

Province of Siena / Poggibonsi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $54 / night

$375 / week

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from $54 / night

(10) Excellent 

10

Province of Siena / Sovicille

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly

 …see more

from $49 / night

$674 - $2807 / week

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from $49 / night

(1) Excellent 

27

Vacation barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Restored Barn, description: this ground floor flat has an entrance with three large glass doors. The main living area has an open fireplace and is divided into a sitting room and a large kitchen. Dining table, wicker armchairs. Sofa bed for one person. From this room th  …see more

from $102 / night

$556 - $1080 / week

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from $102 / night

(4) Excellent 

14

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 mi
  • Child friendly
  • Ask about pets
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from $107 / night

$588 - $909 / week

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from $107 / night

(8) Excellent 

33

Apartment rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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

from $75 / night

$524 / week

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from $75 / night

(1) Excellent 

12

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Green apartment is located at ground floor and easily accessible, perfect for a family. It consists of a fully equipped kitchen where a folding sofa bed for two guests is provided, a bedroom with a double bed, a bathroom with shower, toilet, hairdryer, washing machin  …see more

from $54 / night

$375 / week

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from $54 / night

(33) Excellent 

32

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from $107 / night

$588 - $909 / week

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from $107 / 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 $77 / night

$257 - $540 / week

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from $77 / 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 $54 / night

$364 - $469 / week

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from $54 / 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 $161 / night

$963 - $1444 / week

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from $161 / night

(8) Excellent 

12

Province of Siena / Monteriggioni

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from $65 / night

$428 / week

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from $65 / night

24

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 o  …see more

from $272 / night

$1898 - $2989 / week

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from $272 / 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  …see more

from $161 / night

$1069 - $2459 / week

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from $161 / 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 $348 / night

$2138 - $2994 / week

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from $348 / night

23

Vacation villa with swimming pool in Cetona

Province of Siena / Cetona

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The villa is located in the southermost corner of Tuscany on top of a hill facing Cetona. The views are breathtaking and stretch as far as Città delle Pieve and Orvieto. A short walk (1km) takes guests to the lovely medieval town of Cetona, where they can get fre  …see more

from $275 / night

$1925 - $3849 / week

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from $275 / night

(1) Excellent 

13

Province of Siena / San Giovanni d'Asso

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Pet friendly

 …see more

from $97 / night

$642 - $695 / week

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from $97 / 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 $97 / night

$588 - $620 / week

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from $97 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $134 / night

$824 - $1230 / week

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from $134 / night

(20) Excellent 

49

Vacation cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 mi
  • Child friendly
  • Pet friendly
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom  …see more

from $65 / night

$449 / week

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from $65 / night

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 mi
  • Swimming pool
  • Child friendly

 …see more

from $102 / night

$524 - $1219 / week

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from $102 / night

100

Vacation apartment in Guazzino

Sinalunga / Guazzino

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
Exterior Casa Daria is a charming apartment situated in the centre of the town of Bettole, just a few kilometres from the famous Montepulciano and Cortona, in the beautiful area of the Val di Chiana in the South of Tuscany.  The apartment, which can be fo  …see more

from $59 / night

$375 - $599 / week

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from $59 / night

100

Vacation villa with swimming pool, tennis court in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
 NOTE: THE VILLA IS PRICED FOR UP TO 18 PEOPLE IF YOU ARE A SMALLER GROUP THE RATE WILL BE REDUCED   ExteriorsThis splendid villa near Siena consists of a main house and an annex. The entire property offers stunning views over the surroundings, and it al  …see more

from $1527 / night

$10686 / week

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from $1527 / 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

$428 - $749 / week

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from $75 / 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 $100 / night

$695 - $1593 / week

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from $100 / night

(15) Excellent 

22

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships.The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style  …see more

from $124 / night

$695 - $943 / week

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from $124 / 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 $129 / night

$749 - $1176 / week

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from $129 / night