50 Best Vacation Rentals in Monteriggioni - Holiday Lettings - Cabins

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66 Vacation rentals

(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 $104 / night

$725 / week

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from $104 / night

(7) Very Good 

25

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Located in the center of the region is the ideal base for reaching the many places of historical, artistic and cultural center of Tuscany more real, less than one hour you can reach, San Gimignano, Val d'Orcia, San Galgano, Montalcino, Crete Senesi, Monteriggioni, place …see more

from $70 / night

$415 - $674 / week

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Responds fast!
avg. 2 hours 24 minutes

from $70 / night

(3) Excellent 

31

Vacation farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions. T …see more

from $87 / night

$604 / week

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Responds fast!
avg. 1 hour 50 minutes

from $87 / night

5

Vacation barn in Monteriggioni

Province of Siena / Monteriggioni

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
It renovated barn in the countryside 7 km from Siena. Large garden with yard and outdoor Jacuzzi (May to September). Access ramp to the ground floor consisting of kitchen, large dining table, fireplace and sofa bed and bathroom with shower. On the 1st floor mezzanine sl …see more

from $87 / night

$604 / week

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from $87 / 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 $285 / night

$1989 - $3133 / week

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from $285 / 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 $97 / night

$679 - $1111 / week

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from $97 / night

(3) Excellent 

35

Vacation farmhouse with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
The “borgo Sammonti” was built in the beginning of the 13th century as a fortress in the county of Scorgiano, and it is located near most beautiful and important tuscan cities. The structure is surrounded by woods and it offers many paths for walks and escursions. Th …see more

from $87 / night

$604 / week

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Responds fast!
avg. 1 hour 50 minutes

from $87 / night

8

Vacation farmhouse rental

Province of Siena / Monteriggioni

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Borgo Stomennano will appeal to those who want not just a holiday villa , but who would like to sheer 17th century style and traditional Italian elegance. Written documentation of Stomennano date back to 1254 when in this place was sign …see more

Pricing unknown

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Pricing unknown

6

Vacation b&b in Monteriggioni

Province of Siena / Monteriggioni

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
At 5 km from Siena, apartment situated on the first floor of a typical Tuscan farm. Great location for excursions and tours in the hills of Santa Caterina is equipped with 3 bedrooms, 2 bathrooms and a large kitchen. It is possible to rent the whole apartment or single …see more

from $173 / night

$1151 / week

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from $173 / night

(5) Excellent 

49

Monteriggioni Vacation villa rental

Province of Siena / Monteriggioni

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Monteriggioni Suite A suite with a view of Monteriggioni Immersed in the Tuscan countryside next to the city walls of Monteriggioni, in the valley dominated by the imposing shape of Montemaggio next to Chianti vineyards, between fields of grain, sunfl …see more

from $124 / night

$863 - $2508 / week

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from $124 / night

8

Monteriggioni Vacation home rental

Province of Siena / Monteriggioni

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Suitable for children age 5+
La Volta is a wanderful, bright, spacious farmhouse ideal for families and groups. Ones you enter into the big leaving room you will be struck by the huge fireplace and the cosy atmosphere of the house due to the particulars and warm coloured furniture and the ter …see more

Pricing unknown

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Pricing unknown

10

Vacation home with shared pool in Monteriggioni

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Perfect base for seeing Siena, Florence, San Gimignano and other Chianti towns. Borgo Stomennano is composed by 5 different accommodations that can hos a total of 34 pax. Each villa is beautifully unique, stunning decor and full of character La Corte is at the groun …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

55

Vacation villa in Quercegrossa

Monteriggioni / Quercegrossa

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena. …see more

from $346 / night

$2416 - $4809 / week

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from $346 / night

40

Apartment rental in Monteriggioni with shared pool

Province of Siena / Monteriggioni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
Among woods and vineyard of Siena Chianti, surrounded by a large region considered a natural park , with a dominating and sunny position, you find the ancient rural villane of the XVII century called “Poggiarello”. Unforgettable sunsets, breath-taking landscapes can …see more

Pricing unknown

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Responds fast!
avg. 3 hours 0 minutes

Pricing unknown

(3) Excellent 

16

Vacation home rental

Province of Siena / Monteriggioni

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
The farmhouse is part of the property called Molino Bianco, an old stone mill documented since the eleventh century as a possession of Lambardi family, Lords of Staggia. As an annex of the fortress of Castiglionalto, Molino was inhabited by a Benedictine community until …see more

from $127 / night

$806 - $1508 / week

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Responds fast!
avg. 3 hours 37 minutes

from $127 / night

(1) Excellent 

19

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 100 mi
  • Child friendly
  • Private garden
The 70 m 2 apartment, with terracotta floors and beamed ceilings, is part of a farmhouse situated within a small village nestled in the beautiful hills of Chianti. Ideal for a relaxing vacation or to visit Siena and the surrounding area. Our apartment is composed of: s …see more

from $98 / night

$685 / week

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from $98 / night

(1) Excellent 

6

Apartment rental in Monteriggioni

Province of Siena / Monteriggioni

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
At 5 km from Siena, apartment situated on the first floor of a typical Tuscan farm. Great location for excursions and tours in the hills of Santa Chiara is equipped with 2 bedrooms, 1 bathroom and a large kitchen. On request it is available a hearty breakfast at a cos …see more

from $116 / night

$777 / week

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from $116 / night

(2) Excellent 

14

Monteriggioni Vacation b&b rental

Province of Siena / Monteriggioni

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
the garden is the place where art history, culture and nature come together to make your stay unique.Inside the House you breathe a unique atmosphere thanks to harmonious, welcoming environment is very romantic.Every stay at the garden, which is to admire the magnificen …see more

Pricing unknown

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Pricing unknown

(7) Excellent 

45

Vacation villa in Monteriggioni

Province of Siena / Monteriggioni

6 15 Min stay varies

  • 6 bedrooms
  • Sleeps 15
  • Min stay varies
  • Nearest beach 76 mi
  • Child friendly
  • Air conditioning
The English text is automatically translated by Google Translator in your language. This could cause some imprecisions. This modern 6BR/4BA villa is an enchanted paradise for friends & families with kids (tree house, trampoline, basketball area, soccer & volleyball/bea …see more

from $139 / night

$967 / week

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from $139 / night

(1) Excellent 

13

Monteriggioni Vacation villa rental

Province of Siena / Monteriggioni

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Private garden
Borgo Stomennano will appeal to those who want not just a holiday villa , but who would like to sheer 17th century style and traditional Italian elegance. Written documentation of Stomennano date back to 1254 when in this place was sign …see more

Pricing unknown

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Pricing unknown

(6) Excellent 

22

Apartment rental in Monteriggioni with swimming pool

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi …see more

from $81 / night

$518 - $639 / week

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Responds fast!
avg. 2 hours 9 minutes

from $81 / night

38

Apartment rental in Monteriggioni with shared pool

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
Among woods and vineyard of Siena Chianti, surrounded by a large region considered a natural park , with a dominating and sunny position, you find the ancient rural villane of the XVII century called “Poggiarello”. Unforgettable sunsets, breath-taking landscapes can …see more

Pricing unknown

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Responds fast!
avg. 3 hours 0 minutes

Pricing unknown

19

Vacation home rental

Province of Siena / Monteriggioni

15 30 Min stay varies

  • 15 bedrooms
  • Sleeps 30
  • Min stay varies
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
The structure consists of apartments (surrounded by 30.000 meters of olive trees and wood), charmingly furnished in the old style of Tuscany and telephone line for internet connection. From May 1st until September 15th it's possible to enjoy the swimming pool of 16 x 9 …see more

Pricing unknown

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Responds fast!
avg. 3 hours 0 minutes

Pricing unknown

34

Vacation villa in Monteriggioni

Province of Siena / Monteriggioni

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Near to Siena (8 km), in the Chianti region, apartment in farmhouse (size: 170 m2) for max.6 persons. Swimming pool complex and park 3 km far away. Splendid farm house (18 th century) located on the top of a hill. The property apartment offers you the unique and rare …see more

from $130 / night

$909 - $1370 / week

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from $130 / night

24

Vacation farmhouse rental

Province of Siena / Monteriggioni

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 80 mi
  • Child friendly
  • Pet friendly
The apartment is on the first floor and is part of a partially renovated country house on the medieval castle of Villa (also known as the Villa) in the municipality of Monteriggioni, Siena. It is an apartment there about 80 sqm. Composed by a large living room with kitc …see more

from $75 / night

$524 / week

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from $75 / night

20

Monteriggioni Vacation apartment rental

Province of Siena / Monteriggioni

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Air conditioning
The apartment is located in lawn groundfloor of casal. From the entrance, covered by a Pergola of vines of grape, strawberry, pratino directly from you in a cozy living room and dining room. The fully furnished bedroom with Grandma's furniture is very spacious fully equ …see more

from $50 / night

$346 / week

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from $50 / night

36

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
The suite includes a large kitchen and living-room with sofa double bed, 1 double bedroom and 1 bathroom. From this suite you can reach a private terrace with garden furniture and a fantastic view on the Elsa Valley. Unforgettable sunsets, breath-taking landscapes ca …see more

Pricing unknown

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Responds fast!
avg. 3 hours 0 minutes

Pricing unknown

(1) Excellent 

43

Monteriggioni Vacation apartment accommodation

Province of Siena / Monteriggioni

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
Among woods and vineyard of Siena Chianti, surrounded by a large region considered a natural park , with a dominating and sunny position, you find the ancient rural villane of the XVII century called “Poggiarello”. Unforgettable sunsets, breath-taking landscapes can …see more

from $231 / night

$1611 / week

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Responds fast!
avg. 3 hours 0 minutes

from $231 / night

(2) Excellent 

12

Monteriggioni Vacation hotel apartment rental

Province of Siena / Monteriggioni

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Air conditioning
Relais La Costa is a luxury historical residence situated close to Siena and Monteriggioni, in the middle of the Montagnola Senese. Gently resting on a hill of the Tuscan countryside and surrounded by a walled Park of two hectares surrounded by 50 hectares of forest, th …see more

Pricing unknown

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Pricing unknown

46

Monteriggioni Vacation apartment rental

Province of Siena / Monteriggioni

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
Among woods and vineyard of Siena Chianti, surrounded by a large region considered a natural park , with a dominating and sunny position, you find the ancient rural villane of the XVII century called “Poggiarello”. Unforgettable sunsets, breath-taking landscapes can …see more

from $232 / night

$1624 / week

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Responds fast!
avg. 3 hours 0 minutes

from $232 / night

28

Vacation apartment in Quercegrossa

Monteriggioni / Quercegrossa

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).The mansion is s …see more

from $181 / night

$1266 - $2060 / week

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from $181 / night

17

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi …see more

from $52 / night

$363 / week

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Responds fast!
avg. 2 hours 9 minutes

from $52 / night

(1) Very Good 

40

Vacation cottage in Monteriggioni

Province of Siena / Monteriggioni

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Raspberry is composed of 3 bedrooms, 2 bathrooms (6 people). Large stone cottage, independent of 115 sqm with private garden and a courtyard gazebo both with table, chairs and bbq, where guests can have breakfast or dinner in peace .From the courtyard and can access the …see more

from $127 / night

$886 - $1496 / week

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from $127 / night

36

Monteriggioni Vacation villa rental

Province of Siena / Monteriggioni

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Monteriggioni Suite A suite with a view of Monteriggioni Immersed in the Tuscan countryside next to the city walls of Monteriggioni, in the valley dominated by the imposing shape of Montemaggio next to Chianti vineyards, between fields of grain, sunfl …see more

from $216 / night

$1508 / week

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from $216 / night

22

Vacation townhouse in Monteriggioni

Province of Siena / Monteriggioni

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
A cozy, little house and set in 4.5 hectares of nature with the rest of the world only 5 min. Surrounded by hiking trails from the castle of Monteriggioni slopes leading up to it. short excavation leading to the structure begins right by the Via Francigena, the historic …see more

from $47 / night

$328 - $691 / week

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from $47 / night

4

Vacation farmhouse with shared pool, golf nearby in Monteriggioni

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
The propertyis a twelth century farmhouse, situated in the heart of Tuscany only 2km from the walled town monteriggioni. and surrounded by the siennese hills. The property is 500 meters above sea level surrounded by olive groves and magnificent woodlands, Peaceful …see more

Pricing unknown

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Pricing unknown

6

Vacation home with swimming pool in Monteriggioni

Province of Siena / Monteriggioni

1 4 6 nights min

  • 1 bedroom
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
the hoot of Teo and 'a small barn renovated place in the town of Monteriggioni. In 15 minute drive we are in the center of Siena, 20 min. drive to San Gimignano, and 40 in Piazzale Michelangelo in Florence. In an hour you can 'get on the Tyrrhenian coast in beautiful co …see more

from $230 / night

$1609 / week

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from $230 / night

28

Vacation home rental

Province of Siena / Monteriggioni

3 50 Min stay varies

  • 3 bedrooms
  • Sleeps 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Small villa in the countryside between Siena and Monteriggioni, in a small and peaceful residential area in the whereabouts of the town of Santa Colomba. This is one of the most characteristic and much sought-after areas, not only for its gentle landscape but also for …see more

from $224 / night

$2014 - $2682 / week

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from $224 / night

(4) Excellent 

17

Vacation apartment in Monteriggioni

Province of Siena / Monteriggioni

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Casa Laura is an independent apartment in a restored farmhouse Agriturismo la Magione that is situated on an agricultural estate on a hilltop at about 300 meters above sea level. It offers a wonderful panorama of the surrounding countryside with fields, olive groves, vi …see more

from $81 / night

$564 / week

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Responds fast!
avg. 1 hour 51 minutes

from $81 / night

(2) Excellent 

28

Quercegrossa Vacation villa rental

Monteriggioni / Quercegrossa

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
This beautiful property belongs to the Campalli estate, a huge farm of 750 acres that produces Chianti Classico wine and includes the Castle of Campalli. La Corte di Campalli is an impressive stone-built farmhouse that dates back to the 16th century. It takes its name f …see more

from $620 / night

$4343 - $7628 / week

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from $620 / night