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

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Villas San Gimignano
466 properties
Apartments Siena
433 properties
Apartment rentals Montepulciano
289 properties
Castelnuovo Berardenga
203 properties
Casole d'Elsa
185 properties
Gaiole in Chianti
177 properties
Poggibonsi
168 properties
Pienza
157 properties
Castellina In Chianti
156 properties
Colle di Val d'Elsa
153 properties
Sinalunga
132 properties
Estates Montalcino
130 properties
Rapolano Terme
117 properties
Asciano
109 properties
Cetona
81 properties
Buonconvento
78 properties
Monteriggioni
75 properties
Sovicille
73 properties
San Casciano dei Bagni
72 properties
Radicondoli
70 properties

Province of Siena

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3,895 Vacation rentals

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 $68 / night

$393 - $550 / week

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from $68 / night

(21) 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 $85 / night

$415 - $1011 / week

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from $85 / night

(6) Excellent 

36

Vacation villa with indoor pool in Radicondoli

Province of Siena / Radicondoli

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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

from $337 / night

$2354 / week

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from $337 / 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 $500 / night

$3497 - $5716 / week

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from $500 / night

35

Contignano Vacation home rental

Radicofani / Contignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
Casa Marianna is in the historic center of Contignano, medieval village of the municipality of Radicofani, in the Val d'Orcia, UNESCO World Heritage Site, in the province of Siena Tuscany land of rare beauty. And 'ideal for a family with children (2 + 3 = 5 beds). The …see more

from $85 / night

$583 - $819 / week

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from $85 / night

(65) Excellent 

52

Vacation villa rental

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 mi
  • Swimming pool
  • Child friendly
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro …see more

from $673 / night

$4707 - $10087 / week

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from $673 / night

(13) Excellent 

23

Vacation apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boule …see more

from $228 / night

$1430 - $2080 / week

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from $228 / 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 $79 / night

$594 - $1060 / week

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from $79 / night

(3) 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 $47 / night

$325 - $1110 / week

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from $47 / 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 with its h …see more

from $85 / night

$505 / week

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from $85 / night

(1) Excellent 

7

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located in a panoramic position on a hill crest between the Val d'Orcia and Valdichiana near Montepulciano, Agriturismo Il Casalone offers a holiday unit tastefully furnished in Tuscan country style. One double bed room (king size), one bathroom and a living room with k …see more

from $79 / night

$337 - $583 / week

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from $79 / night

19

Vacation cottage with swimming pool in Cetona

Province of Siena / Cetona

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This charming cottage is made up of a kitchen, a living room with fireplace, a dining room, a study, a guest bathroom and a double bedroom with en-suite bathroom with shower on the ground floor. On the first floor there is a double bedroom with en-suite with shower, …see more

from $439 / night

$3071 - $4326 / week

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from $439 / night

100

Vacation villa with swimming pool in Moltacino

Province of Siena / Moltacino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Exterior Villa Le Fate is a distinguished villa situated in the Sienese countryside, just 3 km (1.8 miles) from Siena, and immersed in the exquisite landscape of vines and olive groves. The villa is an old seventeenth century manor house which has recently been complete …see more

from $354 / night

$2466 - $4707 / week

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from $354 / night

(5) Excellent 

48

Vacation cottage in Castellina In Chianti

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
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

from $135 / night

$628 - $751 / week

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from $135 / 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 $45 / night

$314 / week

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from $45 / 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. Th …see more

from $101 / night

$628 - $707 / week

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from $101 / night

(27) 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 $180 / night

$1177 - $2556 / week

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from $180 / night

31

Asciano Vacation villa rental

Province of Siena / Asciano

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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 $393 / night

$2186 - $4707 / week

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from $393 / 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 $120 / night

$526 - $1436 / week

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from $120 / night

(8) Excellent 

12

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets
Rocca dei monaci, is a finely restored ancient monastery, nestled among the vineyards of the Tuscan hills. It is the ideal place where to spend your holidays in peace and relaxation by living in contact with nature and ideal base to visit the whole Chianti. The apart …see more

from $101 / night

$707 / week

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from $101 / night

(1) Very Good 

18

B&b rental in Montepulciano with shared pool

Province of Siena / Montepulciano

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
In the beautiful ancient Villa ( 1812 ) of the of " Tenuta Argiano in Montepulciano " estate , we rent some bedrooms in B&B treatment . our guest are treated like part of the family and if request they can join the dinner with the owners. this place is ideal also for …see more

from $45 / night

$314 / week

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from $45 / night

(6) Very Good 

39

Vacation villa rental

Province of Siena / Chianciano Terme

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies at 3 kms from the town of Chianciano Terme, one of the most popular thermal Spas in Italy. The villa is located among the hills dividing Val d'Orcia and Valdichiana. The whole property is for your private use and not shared with any other person. The vill …see more

from $225 / night

$1200 - $3026 / week

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from $225 / 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 $88 / night

$600 - $869 / week

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from $88 / night

(6) 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 $169 / night

$1177 / week

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from $169 / 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 $81 / night

$269 - $566 / week

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from $81 / night

20

Vacation villa with swimming pool in Chiusdino

Province of Siena / Chiusdino

6 12 2 nights min

  • 6 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
The Castellare, is an ancient farmhouse recently restored, respecting the original style, closely surrounded by secular Woods, where between a walk and a dip in the pool (mt14x7) you can relax and enjoy the peace and privacy that characterize this luogo.la villa is comp …see more

from $897 / night

$4259 / week

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from $897 / night

(1) Excellent 

27

Vacation barn with swimming pool in Quercegrossa

Monteriggioni / Quercegrossa

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • 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 $106 / night

$740 - $1132 / week

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from $106 / 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

(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

(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

(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 $169 / night

$1121 - $2578 / week

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from $169 / 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 $135 / night

$807 - $1278 / week

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from $135 / night

(12) 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. Th …see more

from $101 / night

$628 - $707 / week

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from $101 / night

(12) Excellent 

24

Vacation apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
.The apartment, Into The Sunset, owes its name to the magnificent views of the hills of Val d'Orcia which you can enjoy from its windows. It is located in the center of Montepulciano, via Collazzi 10, only 200 meters from Piazza Grande, the heart of the city, where you …see more

from $129 / night

$785 - $973 / week

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from $129 / 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 $415 / night

$2466 - $2690 / week

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from $415 / night

(6) Very Good 

43

Gaiole in Chianti Vacation home accommodation

Gaiole in Chianti / Montefienali

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na …see more

from $61 / night

$350 - $785 / week

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from $61 / night

(8) Excellent 

24

Serre di Rapolano Vacation cottage rental

Rapolano Terme / Serre di Rapolano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
If you are looking for a small piece of paradise nestled in the Crete Senesi, the agriturismo ' L'olivo ' is what you are looking for: independent House with swimming pool, parking and private garden in panoramic area 5 minutes drive from the Spa near the town, ideal fo …see more

from $107 / night

$729 / week

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from $107 / night

14

Vacation villa with swimming pool in Monteroni d'Arbia

Province of Siena / Monteroni d'Arbia

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
This detached house with private garden and pool inside an agricultural business cultivated with olive trees, features also a park and views of Siena and is set in the beautiful Sienese countryside, just 3 km from Vescovado and 5 km from Monteroni away. It consists of t …see more

from $353 / night

$2466 - $3587 / week

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from $353 / night

(1) Excellent 

99

Vacation villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa with pool and large garden with fruit trees, halfway between the famous towers of San Gimignano and the charming medieval town of Certaldo Alto. Private entrance with living/dining room with double sofa bed, a kitchen, a bedroom and a bathroom with shower. Entirel …see more

from $141 / night

$863 - $1289 / week

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from $141 / night

(7) 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 $113 / night

$707 - $1177 / week

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from $113 / night

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