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

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Villas San Gimignano
464 properties
Apartments Siena
446 properties
Apartment rentals Montepulciano
296 properties
Casole d'Elsa
206 properties
Colle di Val d'Elsa
199 properties
Castelnuovo Berardenga
192 properties
Gaiole in Chianti
162 properties
Castellina In Chianti
158 properties
Rapolano Terme
155 properties
Poggibonsi
151 properties
Pienza
141 properties
Sinalunga
131 properties
Estates Montalcino
127 properties
Asciano
117 properties
San Casciano dei Bagni
83 properties
Radicondoli
70 properties
Monteriggioni
70 properties
Buonconvento
69 properties
Chianciano Terme
69 properties
Cetona
69 properties

Province of Siena

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3,933 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 $162 / night

$1078 - $2479 / week

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from $162 / 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 $87 / night

$593 - $895 / week

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from $87 / 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 $108 / night

$593 - $916 / week

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from $108 / night

4

Province of Siena / Orgia

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Nearest beach 80 mi
  • Private garden

 …see more

from $18 / night

$126 / week

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from $18 / 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 $81 / night

$485 / week

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from $81 / 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 $97 / night

$388 - $604 / week

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from $97 / 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 $130 / night

$755 - $1186 / week

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from $130 / 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 $87 / night

$475 - $2220 / week

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from $87 / night

23

Vacation apartment rental

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool. Located in the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history,  …see more

from $124 / night

$809 - $1067 / week

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from $124 / night

(34) Excellent 

24

Apartment rental in Val di Merse

Siena / Val di Merse

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Pet friendly
LAST MINUTE OFFER IN APRIL and MAY 2017 !! OFFERTE LAST MINUTE AD APRILE E MAGGIO 2017 !! FURTHER AVAILABILITY DESPITE THE BOOKING CALENDAR, PLEASE, LET'S CONTACT US! The property dates back to the 14th century and for generations has been part of the property  …see more

from $54 / night

$345 - $566 / week

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from $54 / night

48

Fort rental in Montisi with shared pool

Province of Siena / Montisi

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Grancia Country Resort is a romantic and charming 14th century fortress used as a "Grancia", a granary for the storage of the produce grown on the property. Perched next to the delightful hilltop village of Montisi, it overlooks the surrounding Tuscany coun  …see more

from $134 / night

$924 - $1026 / week

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from $134 / 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 $125 / night

$700 - $950 / week

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from $125 / night

(1)  

19

Province of Siena / Cetona

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Suitable for children age 5+
  • Pet friendly

 …see more

from $54 / night

$324 / week

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from $54 / night

24

Apartment rental in Siena with shared pool

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city tha  …see more

from $108 / night

$755 / week

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from $108 / night

(7) Excellent 

35

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

 …see more

from $108 / night

$679 - $1132 / week

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from $108 / night

18

Vacation villa with swimming pool in Chiusi

Province of Siena / Chiusi

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The farmhouse was inhabited by a family of Umbrian farmers whose main occupation was cultivating their land, picking up its hard-earned fruits.The house is now surrounded by a garden with oak-trees, mulberry-trees, laurels, maples and lime-treesOn the in  …see more

from $369 / night

$2263 - $3341 / week

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from $369 / night

10

Siena / Isola d'Arbia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $44 / night

$302 / week

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from $44 / night

(4) Excellent 

19

Vacation farmhouse with swimming pool in San Casciano dei Bagni

Province of Siena / San Casciano dei Bagni

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
San Giacomo is a beautiful country house set in one of the most charming Tuscan landscape.The property is close to the medieval village of SAN CASCIANO DEI BAGNI, known since the Etruscan times for its thermal hot springs.SAN GIACOMO sleeps 8 peple in th  …see more

from $259 / night

$970 - $2716 / week

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from $259 / night

(6) Very Good 

24

Farmhouse rental in Caprera

Siena / Caprera

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Air conditioning
A stylish apartment close to Siena ancient city walls, still surrounded by olive groves and fields; ideal for visitors looking for a quite lodge. The farmhouse is part of a unique Liberty village built by Garibaldi's doctor in 1880. Local shops are at walking dista  …see more

from $205 / night

$1347 / week

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from $205 / night

(7) Excellent 

25

Province of Siena / Siena

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 mi
  • Child friendly

 …see more

from $76 / night

$518 - $787 / week

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from $76 / 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 $239 / night

$1290 - $1885 / week

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from $239 / night

(3) Very Good 

23

Vacation farmhouse with shared pool in Buonconvento

Province of Siena / Buonconvento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Are your looking for an ideal vacation spot to relax and enjoy the magnificently unspoilt Tuscan countryside in the Orcia valley while relaxing with a good book by the pool? Or do you prefer making cultural excursions to any of the numerous surrounding hill towns? well  …see more

from $324 / night

$2263 / week

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from $324 / night

(10) Excellent 

26

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $92 / night

$669 - $927 / week

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from $92 / 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

$593 - $625 / week

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from $97 / night

18

Sarteano Vacation farmhouse rental

Province of Siena / Sarteano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This stone house was originally inhabited by a large family of farmers who worked for the monks of the nearby Abbey of Spineto. Excellent furnishing.Ground floor: large kitchen, with wood fired oven, opening directly onto the garden, spacious dining room, study  …see more

from $490 / night

$3427 - $4839 / week

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from $490 / night

(6) Very Good 

25

Province of Siena / Monteriggioni

1 3 3 nights min

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

 …see more

from $60 / night

$388 - $631 / week

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from $60 / night

(22) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Child friendly
  • Air conditioning

 …see more

from $60 / night

$361 - $523 / week

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from $60 / night

(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
Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, discover more ... Villa LisiDor has been fully renovated beginning of 2016 with all new amenities, with a habitable area of 300 square meters. On GROUND FLOOR, which is at garden level, i  …see more

from $511 / night

$3573 - $5496 / week

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from $511 / night

(1) Excellent 

45

Province of Siena / Montalcino

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $281 / night

$1962 / week

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from $281 / night

22

Vacation home in Montalcino

Province of Siena / Montalcino

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 mi
  • Child friendly
Stay in our beautifully restored townhouse in the historic heart of this prestigious hill town famous for Brunello wine, 30 mins south of Siena. Travertine worktops, marble bathrooms, terracotta floors and chestnut beams. Our property is a three-storey townhouse rece  …see more

from $244 / night

$1244 / week

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from $244 / night

15

B&b rental in Serre di Rapolano

Rapolano Terme / Serre di Rapolano

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
  • Ask about children
  • Air conditioning
Antico Granaione B&B Historical Residence, Authentic Tuscan Hospitality. Antico Granaione b&b, stylish hotel in Tuscany, is located in the characteristic hamlet of Serre di Rapolano close to the thermal spa of Rapolano Terme, Siena. Antico Granaione b&b pr  …see more

from $44 / night

$302 / week

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from $44 / night

(18) Excellent 

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 Cla  …see more

from $81 / night

$399 - $972 / week

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from $81 / night

(2) Excellent 

19

Vacation apartment in Siena

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 mi
  • Child friendly
  • Air conditioning
The apartment overlooks the beautiful Piazza del Campo , with a light coming from the three main windows and invades the entire house is unique about every hour of the day . The apartment has just been renovated and furnished with designer pieces and equipped with every  …see more

from $399 / night

$2371 - $2694 / week

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from $399 / 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 $76 / night

$572 - $1019 / week

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from $76 / 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 $78 / night

$259 - $545 / week

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from $78 / night

(5) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 150 mi
  • Child friendly
  • Private garden

 …see more

from $97 / night

$615 - $733 / week

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from $97 / 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

$679 - $2829 / week

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from $49 / night

(1) Excellent 

21

Province of Siena / Rocca d'Orcia

2 4 2 nights min

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

 …see more

from $76 / night

$539 / week

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from $76 / night

(11) Excellent 

19

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
  • Pet friendly
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 $97 / night

$604 - $679 / week

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from $97 / night

(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

$525 - $832 / week

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from $75 / night

1