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

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Villas San Gimignano
429 properties
Apartments Siena
412 properties
Apartment rentals Montepulciano
313 properties
Casole d'Elsa
201 properties
Gaiole in Chianti
187 properties
Castelnuovo Berardenga
169 properties
Estates Montalcino
167 properties
Poggibonsi
161 properties
Castellina In Chianti
157 properties
Pienza
150 properties
Colle di Val d'Elsa
150 properties
Sinalunga
131 properties
Rapolano Terme
117 properties
Asciano
95 properties
Radda in Chianti
74 properties
Monteriggioni
72 properties
Radicondoli
68 properties
Chianciano Terme
68 properties
San Casciano dei Bagni
67 properties
Sovicille
66 properties

Province of Siena

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3,912 Vacation rentals

(8) Excellent 

35

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 toponym “Strada” attests to these places' historical value. Carefully restored, surrounded by centuries-old cypresses an …see more

from $153 / night

$960 - $1230 / week

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from $153 / night

(29) 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 $223 / night

$1476 - $2776 / week

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from $223 / 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 with solid …see more

from $130 / night

$728 - $988 / week

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from $130 / night

(31) Excellent 

20

Vacation apartment in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • 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 $94 / night

$563 - $785 / week

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from $94 / night

(4) 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 $47 / night

$328 - $1125 / week

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avg. 1 hour 7 minutes

from $47 / 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 $176 / night

$1172 - $2694 / week

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Responds fast!
avg. 49 minutes

from $176 / 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 ... THE VILLA: 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 l …see more

from $555 / night

$3883 - $5973 / week

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from $555 / night

(12) 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 disa …see more

from $93 / night

$511 - $2392 / week

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from $93 / night

(9) Very Good 

16

Apartment rental in Siena

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Car not necessary
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo. You will not need anymore to walk up 66 steps to access this apartment,because now there is a new elevator to lift you on two amazing terraces and their spectacular views. The main l …see more

from $82 / night

$902 - $1640 / week

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Responds fast!
avg. 3 hours 55 minutes

from $82 / night

22

Siena Vacation apartment rental

Province of Siena / Siena

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
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 $211 / night

$1476 / week

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from $211 / night

49

Vacation apartment in Colle di Val d'Elsa

Colle di Val d'Elsa / Montegabbro

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 60 mi
  • Child friendly
  • Ask about pets
Apartment in a very small Medieval village. The building was a Benedectine Monastery. The village Montegabbro is in the hearth of Tuscany, it's at 15 minutes by car to San Gimignano, Volterra and Colle di Val d'Elsa. Siena is at 30 minutes, Florence is at 45 m …see more

from $71 / night

$410 - $574 / week

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Responds fast!
avg. 3 hours 34 minutes

from $71 / night

34

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Girasole (2 + 2) The “Girasole” apartment on the ground floor with independent access has a roomy kitchen with a large original century fireplace. One double bedroom and one double sofa- bed in the small living room make it suitable for a couple or a young family. It …see more

from $82 / night

$492 - $949 / week

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from $82 / night

(4) 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 $49 / night

$340 - $1160 / week

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Responds fast!
avg. 1 hour 7 minutes

from $49 / night

(1) Very Good 

19

Vacation apartment in Isola d'Arbia

Siena / Isola d'Arbia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Delicious partment placed in a texturized vintage building protected by the Italian cultural heritage, situated in a medieval village, a few minutes from the center città.Restrutturato in rustic style, with a strong romantic note. The apartment consists of two bedrooms, …see more

from $47 / night

$328 / week

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Responds fast!
avg. 1 hour 51 minutes

from $47 / 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 from Pisa, Florenc …see more

from $82 / night

$621 - $1107 / week

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Responds fast!
avg. 2 hours 5 minutes

from $82 / night

(1) Very Good 

39

Vacation apartment rental

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Ask about pets
Apartment of approximately 70 m2, on the ground floor of an ancient building in the historical centre of Siena, just a few metres from the Accademia Chigiana and behind Piazza del Campo. Composed of living room, kitchen, bathroom, spacious bedroom with a double bed and …see more

Pricing unknown

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Pricing unknown

(45) 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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Responds fast!
avg. 2 hours 5 minutes

from $240 / night

6

Apartment rental in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Independent apartment in detached house for rent situated in Montepulciano station with independent entrance and parking space consisting of 2 bedrooms, living room, kitchen, bathroom with shower and washing machine. It is ideal to accommodate 4 persons of the same fami …see more

Pricing unknown

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Pricing unknown

(3) Excellent 

23

Vacation apartment with shared pool, golf nearby in Buonconvento

Province of Siena / Buonconvento

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 guests a truly uni …see more

from $100 / night

$656 - $1148 / week

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Responds fast!
avg. 3 hours 39 minutes

from $100 / night

(2) Excellent 

18

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly
The old farm of the Aquila (Eagle in French) is an atypical Tuscan country house, situated on the hills of the Chianti Classico region, near Gaiole Chianti. The panoramic position gives you the opportunity to enjoy a view of breathtaking on the surrounding woods, hills …see more

from $106 / night

$738 / week

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Responds fast!
avg. 2 hours 47 minutes

from $106 / night

(9) Very Good 

41

Vacation farmhouse with shared pool in Montepulciano

Province of Siena / Montepulciano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
The main arched entrance leads past a utility room and downstairs bathroom into the open plan kitchen and dining room with dining table for 6 guests. The lounge has two sofa's one of which is a comfortable double sofa bed There is a wood burning stove in the lounge for …see more

from $130 / night

$813 - $1164 / week

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from $130 / night

(3) Excellent 

32

Siena Vacation condo rental

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
L 'apartment is on the third floor in a residence d' era of the late '700, in the heart of the historic center of Siena. L 'apartment, about 80 meters, is characterized by beautiful frescoed ceilings and antique beams. With lift, it consists of a 'large living room, din …see more

from $141 / night

$844 - $1336 / week

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from $141 / night

19

Vacation farmhouse with swimming pool in Palazzone

Province of Siena / Palazzone

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Wonderful independent villa with private pool situated in the proximity of the Val d’Orcia region, in the surroundings of San Casciano dei Bagni, a small town renowned for its beautiful hot springs. This villa has been recently restored an turned into an elegant country …see more

from $1066 / night

$7457 - $10844 / week

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from $1066 / night

(9) Very Good 

6

Valiano Vacation home rental

Montepulciano / Valiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Pet friendly
Small detached house with a ground floor of 22 square meters with living room and fitted kitchen and master bedroom on the first floor with bath. A Valiano, quiet old town in a strategic position to visit the city of art and nature: Montepulciano, Siena, Cortona, Lake T …see more

from $59 / night

$410 / week

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from $59 / night

25

Vacation tower with swimming pool in Radda in Chianti

Province of Siena / Radda in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
A view on a scenic wine and olive oil country. The ancient farmhouse of Augusto and Lele Vitali is an excellent base from which to explore the "heart" of Tuscany. A few meters off the road to the village, the Torre, facing Radda, stands in an olive grove overlooking vin …see more

from $164 / night

$1113 / week

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from $164 / night

(16) Excellent 

Certificate of Excellence

34

Vacation apartment in Poggibonsi

Province of Siena / Poggibonsi

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Comfortable apartment (110 m2) in a villa consisting in the '70s located in the Chianti hills, about 3 km from Poggibonsi, halfway between Florence and Siena. The most beautiful Chianti region villages like Castellina and Radda in Chianti or the town of San Gimignano wi …see more

Certificate of Excellence

from $153 / night

$1066 - $2214 / week

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Responds fast!
avg. 2 hours 40 minutes

from $153 / night

8

San Gusme Vacation apartment rental

Castelnuovo Berardenga / San Gusme

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
intimate studio for 2 people with a small kitchen, ideal for couples who want tranquility and comfort. Large bathroom with shower and even a jacuzzi corner. The apartment is reached after traveling a dirt road from the Roman period, and therefore protected by Unesco. Ar …see more

from $70 / night

$484 / week

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from $70 / night

22

Vacation farmhouse with shared pool in Isola d'Arbia

Siena / Isola d'Arbia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $126 / night

$550 - $1501 / week

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from $126 / night

23

Vacation villa in Volpaia

Radda in Chianti / Volpaia

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
La Commenda is located in a quiet and secluded position in the Volpaia hamlet. This small, rural hamlet with its fortified walls dating from Medieval times, is one of the best remaining examples of its kind in Tuscany. It is located, just north of Radda in Chianti, in a …see more

from $422 / night

$2952 - $4662 / week

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from $422 / night

(1) Excellent 

32

Vacation home in Le Piazze

Province of Siena / Le Piazze

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
The house has three floors and it is simple furnished. The ground floor has a living room with a kitchen and a double bedroom with bathroom. In the second floor there's a double bedroom with a beautiful panorama view and a big bathroom with a nice bathtub in the centre. …see more

from $58 / night

$352 - $574 / week

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Responds fast!
avg. 2 hours 58 minutes

from $58 / night

(47) 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 $117 / night

$813 - $1170 / week

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Responds fast!
avg. 3 hours 48 minutes

from $117 / night

(3) Excellent 

24

Vacation apartment in Staggia Senese

Poggibonsi / Staggia Senese

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
Ideally located for visiting the most famous cultural sites in Tuscany for a holiday dedicated to art, culture and culinary tradition. Relaxation guaranteed by the beautiful setting of rolling hills on the edge of Chianti Easily accessible by car, just 5 km away from Co …see more

from $41 / night

$238 - $399 / week

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from $41 / 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
  • Swimming pool
  • Child friendly
  • Pet 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 $92 / night

$627 - $908 / week

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from $92 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
Ginestra [200 sqm] This House is a restored barn and it was restored in 2008. Ginestra farmhouse 6/7 persons The main entrance is at ground floor up 2 steps from the gardenThe entrance is directly into the dining room. Through an open door passage and down 1 step t …see more

from $235 / night

$1640 - $2577 / week

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from $235 / night

(8) Very Good 

48

Montepulciano Vacation home rental

Province of Siena / Montepulciano

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Ask about pets
Tuscan-style villa, very close to Montepulciano's historic centre within walking distance. Located on the mezzanine level, is well decorated and features large terraces overlooking the countryside and the beautiful view of the city of Montepulciano. The House (approx. 1 …see more

from $94 / night

$645 - $703 / week

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from $94 / night

20

Apartment rental in Piancastagnaio

Province of Siena / Piancastagnaio

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 mi
  • Child friendly
  • Pet 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 $116 / night

$645 / week

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from $116 / night

(5) Very Good 

Certificate of Excellence

21

Vacation townhouse rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 mi
  • Swimming pool
  • Child friendly
Beautiful apartment situated in an ancient hamlet on the ground floor of a two-storied House with an enchanting view on the heart of the Tuscan Countryside, 3 km from the centre of San Gimignano, Worlwide Heritage Town of UNESCO. The apartment is composed of 1 double be …see more

Certificate of Excellence

from $147 / night

$855 - $1300 / week

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from $147 / night

(12) Excellent 

Certificate of Excellence

26

Vacation home in Montepulciano

Province of Siena / Montepulciano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
The Corolline is located about 1.5 km from the historic centre of Montepulciano, immersed in the tranquillity and silence of the Tuscan countryside. The structure has been recently renovated, rustic style, outside is a beautiful garden. The central location is strategi …see more

Certificate of Excellence

from $94 / night

$738 - $1008 / week

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from $94 / night

(2) Excellent 

24

Vacation apartment with golf nearby in Colle di Val d'Elsa

Province of Siena / Colle di Val d'Elsa

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
You will be charmed by the sense of freedom ', ample space and comfort offering the house: 3 bedrooms - A double bedroom and single bed finishing has tiled floors, floral painted ceiling, furniture style years 50 - B double room with twin beds painted walls, carved furn …see more

from $94 / night

$656 / week

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from $94 / night

(5) Excellent 

24

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Podere Torricchi is in a typical tuscan landscape characterised by hills with olive trees and mediterrenean bush. Podere Torricchi is a group of converted farm buildings. The apartment has been newly restored in a traditional Tuscan style. Gambassi Terme and San …see more

from $82 / night

$574 - $1347 / week

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Responds fast!
avg. 3 hours 34 minutes

from $82 / night