25 Best Vacation Rentals in Monticiano - Holiday Lettings - Cabins

Close

Monticiano

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

34 Vacation rentals

(6) Excellent 

35

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 $79 / night

$516 - $1088 / week

Book View

from $79 / night

(2) Excellent 

40

Vacation b&b rental

Monticiano / Iesa Palazzo

6 9 1 night min

  • 6 bedrooms
  • Sleeps 9
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
The Farm She is immersed in the green hills of Siena, close to sulphur Baths of Petriolo famous for the curative powers of its waters. Within walking distance is the Abbey of San Galgano and the Hermitage of Montesiepi, where he kept the sword in the stone. The farmhous …see more

from $202 / night

$1345 / week

Book View

from $202 / night

31

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 $79 / night

$505 - $538 / week

Book View

from $79 / night

(7) 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 $90 / night

$628 / week

Book View

from $90 / 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 $143 / night

$989 / week

Book View

from $143 / night

100

Vacation villa with swimming pool 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
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

from $1233 / night

$8406 / week

Inquire View

from $1233 / night

(1) 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 $68 / night

$449 / week

Book View

from $68 / 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 $101 / night

$673 - $1261 / week

Book View

from $101 / 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 $133 / night

$925 / week

Book View

from $133 / 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

Book View

Pricing unknown

23

Vacation villa with swimming pool in Monticiano

Province of Siena / Monticiano

9 9 Min stay varies

  • 9 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Leccio is a world apart set in a charming and peaceful place where guests can truly relax and rediscover a calmer pace of life, away from the city. The villa is nesteled in the beautiful unspoiled widerness of a natural reserve. It is close to Siena and to San Gal …see more

Pricing unknown

Inquire View

Pricing unknown

(4) Excellent 

96

Vacation villa 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
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 $1233 / night

$8406 - $13655 / week

Book View

from $1233 / night

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

from $137 / night

$947 - $975 / week

Book View

from $137 / night

22

Vacation villa with swimming pool in Monticiano

Province of Siena / Monticiano

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Staying at Villa Renata is a unique experience, here the nature is wild and people have maintained the simplicity and genuineness of their ancestors farmers Villa Renata is managed directly by their owners who want to offer to their guests a "happy holiday", informal bu …see more

from $195 / night

$1670 - $2502 / week

Book View

from $195 / 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 $73 / night

$510 - $589 / week

Book View

from $73 / 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 $79 / night

$505 - $662 / week

Book View

from $79 / 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 $3567 / night

$24964 - $33285 / week

Inquire View

from $3567 / night

38

Vacation villa with swimming pool in Monticiano

Province of Siena / Monticiano

14 28 7 nights min

  • 14 bedrooms
  • Sleeps 28
  • 7 nights min
  • Swimming pool
  • Private garden
Villa delle Stelle – Monticiano Siena – Tuscany 14 Double Bedrooms – Swimming Pool - Spa Villa delle Stelle is a residence in an unspoiled setting, offering state-of-the-art amenities and technologies. It is located to the south of the historic city of …see more

from $3567 / night

$24964 - $33285 / week

Book View

from $3567 / night

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 $144 / night

$998 / week

Book View

from $144 / 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 $236 / night

$1569 / week

Book View

from $236 / night

34

Vacation apartment in Monticiano

Province of Siena / Monticiano

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 70 mi
  • Child friendly
  • Private garden
Lovely apartment restored with attention to details, in typical Tuscan style, equipped with every comfort, set close to the main facilities of the town of Iesa (SI). It is located on the first floor of a small stone building and consists of a spacious living room with a …see more

from $68 / night

$449 / week

Book View

from $68 / 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 $79 / night

$449 / week

Book View

from $79 / night

20

Monticiano Vacation home rental

Province of Siena / Monticiano

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
(Minimum of one week rental required) In the center of the small hamlet of Scalvaia, 500 above sea level, The Trellis villa is a delightful newly restored house with private pool and garden. Scalvaia is a small village with only 70 inhabitants right at the border betwee …see more

from $166 / night

$1156 - $2056 / week

Inquire View

from $166 / night

20

Vacation home rental

Province of Siena / Monticiano

14 27 7 nights min

  • 14 bedrooms
  • Sleeps 27
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
(Minimum of one week rental required) Villa Tocchi is located in the valleys of the Merse River, in the south of the province of Siena, not far from Montalcino and Pienza. You're not going to come across the place by chance, it lies well off the beaten track. Here life …see more

from $4923 / night

$34460 - $45946 / week

Inquire View

from $4923 / night

69

Vacation villa in Monticiano

Province of Siena / Monticiano

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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: Thi …see more

from $2394 / night

$16755 - $22358 / week

Inquire View

from $2394 / 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 $129 / night

$903 / week

Book View

from $129 / 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 $118 / night

$824 / week

Book View

from $118 / night

20

Vacation home in Monticiano

Province of Siena / Monticiano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
(Minimum of one week rental required) Additional amenities include: living room, car recommended, views, caretaker, cook available on request, staff available, heating, crib, pool 11 x 5.5 meters, dining room, walkable, gardener available. …see more

from $248 / night

$1734 - $3186 / week

Inquire View

from $248 / 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 $141 / night

$981 / week

Book View

from $141 / night

20

Home rental in Monticiano

Province of Siena / Monticiano

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
(Minimum of one week rental required) Located on a verdant hilltop just off of a short country road, La Casetta di Monticiano offers lovely views over the forested hills. Completely surrounded by a fenced garden the cottage is on the ground floor and consists of a livin …see more

from $136 / night

$946 - $1290 / week

Inquire View

from $136 / night

21

Villa rental in Monticiano with shared pool

Province of Siena / Monticiano

7 13 7 nights min

  • 7 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
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. Beautiful view. Private, equipped outdoo …see more

from $201 / night

$1404 - $3230 / week

Inquire View

from $201 / night

(1) Good 

14

Vacation home in Monticiano

Province of Siena / Monticiano

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Pet friendly
(Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. The Wishing Well is newly remodeled home located just outside the village of Monticiano which is 35 kilometers from Siena. This beautiful stone house t …see more

from $188 / night

$1311 - $2691 / week

Inquire View

from $188 / 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 $141 / night

$981 / week

Book View

from $141 / night

21

Home rental in Monticiano

Province of Siena / Monticiano

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Ask about pets
"Il Casale", 4-room house 110 m2 on 2 levels, on the ground floor, rustic and cosy furnishings: living/dining room with open-hearth fireplace and satellite TV. Exit to the patio. Open kitchen (4 hot plates, mini-oven, oven, dishwasher) with dining table, open-hearth fir …see more

from $93 / night

$655 - $982 / week

Book View

from $93 / night

1