25 Best Vacation Rentals in Monticiano - Holiday Lettings - Cabins

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1,887 Vacation rentals

(2) Excellent 

14

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 mi
  • Child friendly
  • Ask about pets
This apartment is in the historical center of a beautiful town near Siena. Its name is Monticiano. It's composed by 2 bedrooms (for 4 gests), 1 bathroom (with a shower box), 1 indipendent kitchen and a great dining room. The apartment is 75 mq. In the centre of this vi …see more

from $70 / night

$465 / week

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from $70 / night

(1) Excellent 

39

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Nearest beach 40 mi
  • Child friendly
  • Pet friendly
My house is located in iesa a charming village in the heart of the Val di Merse halfway between Siena and Grosseto 15 km from the Abbey of San Galgano and 6 km from the sulfur baths of Petrillo ... great place for families to relax Fresh air and enjoy the peace and quie …see more

from $47 / night

$291 / week

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from $47 / night

(8) Very Good 

20

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Casa Gigliola, holiday villa near Siena, can accommodate up to 7 people and is perfect for a large family or a group of friends, has private parking space, a large balcony and easy access to the village swimming pool. The house is located in Monticiano, a medieval v …see more

from $93 / night

$650 / week

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avg. 3 hours 34 minutes

from $93 / night

44

Vacation home in Monticiano

Province of Siena / Monticiano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Studio apartment with large and airy living room, 4 bedrooms, private garden and apartment with a double bedroom, 2 sofa beds, a bathroom, a spacious living room, 4 beds, private garden. Our House is situated in an ancient medieval village on the outskirts of Siena, jus …see more

from $76 / night

$529 - $610 / week

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from $76 / night

29

Monticiano Vacation townhouse rental

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 50 mi
  • Ask about children
  • Pet friendly
Podere Leccetro is a farm holiday cottage situated in the natural Park of Val di Merse, only a 30-minute drive from Siena city centre. Near San Galgano Abbey and Terme Petriolo. The farm, situated in a glade circled by woods of elm, oak and chestnut trees, is surrounde …see more

from $82 / night

$488 - $523 / week

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from $82 / night

24

Vacation tower rental

Monticiano / Tocchi

1 5 5 nights min

  • 1 bedroom
  • Sleeps 5
  • 5 nights min
  • Nearest beach 39 mi
  • Suitable for children age 5+
  • Air conditioning
In 1100 it was the guardian of the castle to control who arrived by road and open the great gate to the courtyard. For years, probably for centuries. It was storing for hay and farm tools, shelter for animals and travellers; Today, after years of careful restoration Th …see more

from $105 / night

$697 - $1,306 / week

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from $105 / night

(7) Excellent 

38

Vacation farmhouse in Monticiano

Monticiano / Tocchi

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 mi
  • Child friendly
  • Pet friendly
Podere Leccetro is a farm holiday cottage situated in the natural Park of Val di Merse, only a 20-minute drive from Siena city centre. Near San Galgano Abbey and Terme Petriolo. The farm, situated in a glade circled by woods of elm, oak and chestnut trees, is surrounded …see more

from $87 / night

$535 - $1,127 / week

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from $87 / night

20

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Rustic and charming 50 sq.mt first-floor one bedroom apartment in traditional Tuscan villa with pool. Sleeps 2. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Decorative fireplace (not working). Bedroom with double bed and ensuite bat …see more

from $149 / night

$1,034 / week

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Responds fast!
avg. 3 hours 45 minutes

from $149 / night

16

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Cozy 34 sq.mt. apartment in Tuscan villa with pool. Sleeps 2. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Double bed. Bathroom with shower. Designer ceiling fan for summer cooling. Essential food facilities: 2-ring gas hob, extractor …see more

from $137 / night

$958 / week

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avg. 3 hours 45 minutes

from $137 / night

(4) Excellent 

96

Vacation villa in Monticiano

Province of Siena / Monticiano

9 18 2 nights min

  • 9 bedrooms
  • Sleeps 18
  • 2 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Holiday and wedding villla, accommodates up to 18 people. Large tended outdoor green areas with 11x9 private pool. Tucked away yet not isolated. All necessary amenities in the village only 3 minutes walking distance. Refurbished keeping it's authentic, rustic and tas …see more

from $1,278 / night

$8,709 - $13,683 / week

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avg. 3 hours 45 minutes

from $1,278 / night

17

Monticiano Vacation villa rental

Province of Siena / Monticiano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 48 mi
  • Swimming pool
  • Child friendly
It is a peacefull south-east oriented villa located in the hills of Tuscany between Siena and Porto Santo Stefano. The villa dominates the valley. The landscape is astonishing and Villa Banfi, the best Brunello's producer is the characterizing element of the background. …see more

from $244 / night

$1,626 / week

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from $244 / night

84

Villa rental in Monticiano with swimming pool

Monticiano / Tocchi

14 27 7 nights min

  • 14 bedrooms
  • Sleeps 27
  • 7 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
This exclusive luxury villa nestled in the hills of the Tuscan countryside in the south of the province of Siena offers top-quality accommodation completed by first-class services and panoramic views in a natural biogenetic reserve in the Val di Merse. Villa Osse …see more

from $3,695 / night

$25,865 - $34,487 / week

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from $3,695 / night

18

Apartment rental in Monticiano

Province of Siena / Monticiano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Entrance Kitchen with dining area Bathroom Living room Master bedroom Monticiano is a typical ancient Tuscany village, 7 Km away from Terme di Petriolo, an old thermal town with hot spring facilities open all the year . Situated at 35km from Siena and Grosseto, this ti …see more

from $82 / night

$465 / week

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from $82 / night

(3) Very Good 

20

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Nearest beach 65 mi
  • Child friendly
  • Air conditioning
The apartment (60m2 - approx. 600 sqf) is located on the top floor and is made up of 4 beautifully-decorated rooms with a light blue pastel colour motif. The holiday flat has one double bedroom, with ample storage space and in the living room there is a double sofab …see more

from $82 / night

$523 - $685 / week

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Responds fast!
avg. 3 hours 34 minutes

from $82 / night

4

Vacation farmhouse rental

Province of Siena / Monticiano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
In the quiet of the Sienese hills The Castellare is well-located for those wanting a relaxing holiday and for those who want to discover artistic and natural beauties. It is a typical country house with two apartments for guests and an apartment for owners. It is surrou …see more

Pricing unknown

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Pricing unknown

100

Vacation villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Exteriors This rental villa has been restored maintaining authentic, rustic Tuscan style and has a 11 x 6 x 190 swimming pool. Its landscaped gardens offer plenty outdoor areas with garden furnishings. This Tuscan rental villa is nestled within a wildlife reserve just …see more

Pricing unknown

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Pricing unknown

15

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Lovely 02 people middle floor 36 sq.mt apartment in traditional Tuscan villa with pool. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Double bed. Bathroom with shower. Designer ceiling fan for summer cooling. Essential food facilities: …see more

Pricing unknown

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Responds fast!
avg. 3 hours 45 minutes

Pricing unknown

14

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Charming 52 sq.mt attic apartment in traditional Tuscan villa with pool. Sleeps 2/4 people. Authentic interiors with terracotta floors and chestnut wood beamed ceilings. Bedroom with double bed and ensuite bathroom with shower. Additional comfortable double sofa b …see more

from $149 / night

$1,034 / week

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Responds fast!
avg. 3 hours 45 minutes

from $149 / night

11

Vacation apartment in Monticiano

Province of Siena / Monticiano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
It is part of a tourist complex located 3 kilometers from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the Lower Merse. The apartment consists of a living kitchen, a double bedroom, a bedroom with two single beds and a bathroom. Als …see more

from $146 / night

$1,016 / week

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from $146 / night

17

Vacation villa in Monticiano

Province of Siena / Monticiano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:VILLAthis property - NEAR MONTICIANO this property is a beautifully presented converted barn, located just 1.2km from the village of Monticiano. The villa is private and surrounded by a lovely garden with salt-water swimming pool (11m x 5.50m, 1.10m/ …see more

from $515 / night

$1,780 - $3,603 / week

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from $515 / night

21

Vacation villa in Monticiano

Province of Siena / Monticiano

7 13 Min stay varies

  • 7 bedrooms
  • Sleeps 13
  • Min stay varies
  • Child friendly
  • Pet friendly
Owner's description:Main Description : Farmhouse in the hills in the near of the small village of Monticiano (1,5 km) in the heart of the Tuscan countryside from where you can easily reach the most interesting touristic places both on the countryside and on the coast. B …see more

from $403 / night

$1,355 - $2,821 / week

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from $403 / night

61

Vacation home with swimming pool in Monticiano

Province of Siena / Monticiano

14 28 1 night min

  • 14 bedrooms
  • Sleeps 28
  • 1 night min
  • Swimming pool
  • Child friendly
Villa Fassio is a 13th century independent farmhouse located in an untouched area of land, offering both comfort, luxury and the best of modern conveniences. Perched on top of a hill in Southern Siena, Villa Fassio has 360 degree views of the surrounding Tocchi and Bass …see more

from $4,176 / night

$29,232 / week

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Responds fast!
avg. 1 hour 21 minutes

from $4,176 / night

15

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the Lower Merse. It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the L …see more

from $122 / night

$854 / week

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from $122 / night

12

Vacation villa in Monticiano

Province of Siena / Monticiano

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:Villa is a world apart, set in a charming and peaceful place where guests can truly relax and discover a slower pace of life away from the city. The villa is nestled in the beautiful, idyllic wilderness of a natural reserve. It is close to Siena and …see more

from $1,420 / night

$9,207 - $9,944 / week

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from $1,420 / night

40

Vacation villa with swimming pool in Monticiano

Province of Siena / Monticiano

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Huge villa located 26 km from the city of Siena with 8 bedrooms (all with en suite bathroom) able to host up to 16 guests. The villa is equipped with swimming-pool, sauna, astronomical observatory and provides several activities to the guests. External Description: This …see more

from $2,355 / night

$16,482 - $21,992 / week

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from $2,355 / night

17

Vacation villa in Monticiano

Province of Siena / Monticiano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Owner's description:Additional information:This is a beautiful 3 bedroom property located in Tuscany, Italy.This villa, in Monticiano, is a comfortable property sleeping 6 people.The property has 2 bathrooms.The villa offers superb accommodation, including modern luxuri …see more

from $492 / night

$1,925 - $3,449 / week

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from $492 / night

17

Vacation apartment rental

Province of Siena / Monticiano

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the Lower Merse. It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the L …see more

from $134 / night

$935 / week

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from $134 / night

16

Vacation apartment rental

Province of Siena / Monticiano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly
It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the Lower Merse. It is part of a resort located 3 km from the highway Siena / Grosseto, nestled among the green hills of Siena, the Oasis of the L …see more

from $146 / night

$1,016 / week

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from $146 / night