List your home
Apply filters
£ to

Holiday homes 37

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
37 Results   |  

Very Good 4.5/5 

20 Photos

Province of Siena / Monticiano

Apartment / 2 Bedrooms / sleeps 7

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £41 / night

£282 - £500 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Monticiano is one of the most beautiful villages of the Val di Merse, a wild and unspoilt natural area, covered in woods and rich in rivers and hot springs, dotted with castles, abbeys, little countryside churches and ruins, countryside villas and small quiet hamlets.  …see more


2 Sep 2014

5/5

"A fantastic taste of Italian life."

we highly recommend this fabulous apartment which is furnished beautifully and extremely comfortable. The rooms were spacious and cool and the beds were made with delicious Italian linen. We had the u… More


6 Jun 2013

5/5

"Séjour parfait, vacances idéales"

Un accueil parfait, une maison entretenue comme si les propriétaires y habitaient ! On est bien loin de bon nombre de locations saisonnières ... Donc séjour parfait, vacances idéales ... cerise su… More


3 May 2015

4/5

"Best landlady"

We spent three weeks in this apartment with our three teenage children. The landlady is sweet and although we don't speak Italian and she does not speak English, we got on very well. She even supplied… More

See all reviews Continue

Very Good 4.5/5 

20 Photos

Province of Siena / Monticiano

Apartment / 1 Bedroom / sleeps 5

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £41 / night

£282 - £356 / week

View

Key info:

  • Nearest beach 65 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Toscana, Tuscany, SanGalgano, Monticiano, Siena, Firenze, Pisa, Volterra, Holidays, garden, SPECIAL PRICE IS FOR 1 PERSON  …see more


19 Aug 2014

5/5

"Semplicemente perfetta!"

Ho affittato per conto di amici che venivano a trovarmi una settimana questo appartamento. E' perfettamente arredato, attrezzato con tutto il necessario ed anche di più e pulitissimo. Il top è la … More


9 Apr 2015

4/5

"Excellent time"

Pilar and Grazziele are amazing hosts. Pilar speaks english so it makes everything easier. You can go easily to Siena, Montepulciano or Firenze by car in less than an hour. People in Monticiano are… More

See all reviews Continue

100 Photos

Province of Siena / Monticiano

House / 3 Bedrooms / sleeps 5

Short stays welcome

Add to shortlist

from £56 / night

£388 - £593 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
"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

Featured properties

Very Good 4.5/5 

21 Photos

Province of Siena / Monticiano

Villa / 9 Bedrooms / sleeps 18

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £755 / night

£5282 - £5564 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Ideal family and wedding Tuscan villa with private salt water pool. Tucked away yet not isolated. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more


10 Jul 2015

5/5

"Perfect in every way"

Coming to Villa Podernova was the absolute highlight of our holiday. We found the place by accident as we had to move from our original villa (long story!!). Hosts were so welcoming as was Spike the… More


16 May 2015

5/5

"Amazing"

We stayed at this villa for a friends wedding and we completely loved it. The property is beautiful and well managed. The rooms are simple and very country style. We loved the huge garden and the tree… More


30 Apr 2013

4/5

"un podere caratteristico curato nel dettaglio e pieno di charme"

Un podere bellissimo, immerso nel verde delle colline senesi, circondaro dalla natura ma allo stesso tempo a 10 min a piedi da Monticiano dove si puo fare la spesa o cenare. Le camere e gli appartame… More

See all reviews Continue

16 Photos

Province of Siena / Monticiano

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £83 / night

£581 - £599 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Cozy hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

Excellent 5/5 

28 Photos

Monticiano / Iesa Palazzo

B&B / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £57 / night

£395 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Situato nel piccolo borgo di Iesa, frazione di Monticiano, il casale mette subito a proprio agio, la gestione è a conduzione familiare e il clima che vi si respira fa sentire l'ospite a casa. Attenzione i prezzi visualizzati si intendono a camera, per due ospiti, al gi  …see more


20 Dec 2014

5/5

"Fantastico soggiorno all'insegna del relax"

Consiglio a tutti questo bellissimo luogo per una vacanza all'insegna del relax. All'interno del podere c'è una grande piscina con vista panoramica. Si può soggiornare nelle camere o anche in appart… More

See all reviews Continue

Excellent 5/5 

10 Photos

Province of Siena / Monticiano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £36 / night

£247 - £282 / week

View

Key info:

  • Nearest beach 60 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
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.  …see more


21 Oct 2014

5/5

"wonderful location and terrific accommodations!"

our host and hostess where lovely, the apartment in a wonderful Tuscan town, with a local market and square. Mr Bani provided a local map of Tuscany and helped us make choices visiting surrounding d… More

See all reviews Continue

Excellent 5/5 

33 Photos

Monticiano / Tocchi

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £51 / night

£353 - £423 / week

View

Key info:

  • Nearest beach 50 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
COMPLETELY INDEPENDENT BIG APARTMENT WITH 2 BEDROOMS AND 2 BATHROOMS WITH SOFA BED CAN ACCOMMODATE UP TO 6 PEOPLE During the spring and summer guests can follow the work of Francesco with bees  …see more


18 Jul 2012

5/5

"The perfect place to relax, be quiet and enjoy nature"

I have been at the Podere Leccetro in June 2012 - was looking for a nice and quiet place to write. Must say that it was a good choice, the renovated flat is of an excellent standard and the place is … More


18 Aug 2014

5/5

"Vacanza in relax"

Splendido posto..appartamenti veramente accoglienti..I proprietari Francesco e Giulia sono veramente carini..lo consiglio vivamente. ..ci rivediamo erika e oscar P.s. shana (il nostro pastore tedesco)… More


23 Mar 2013

5/5

"Relax e Natura"

Posto meraviglioso con un contesto naturale incantevole (per passeggiate e relax), struttura per le vacanze eccellente. Francesco e Giovanna (gestori del Podere) due persone incantevoli che hanno cont… More

See all reviews Continue

22 Photos

Province of Siena / Monticiano

Villa / 3 Bedrooms / sleeps 7

2 Nights min stay

Add to shortlist

from £121 / night

£846 - £1557 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Renata is an independent villa with natural salted ecological pool and garden, located just on the edge of the residential area of the village of Monticiano but still immersed in the green countryside . Check in from 16,00 to 19,00. For a different check-in time  …see more

25 Photos

Province of Siena / Monticiano

House / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £29 / night

£198 - £346 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Casa nel centro storico con ampio e appartato giardino con vista panoramica alle porte di Siena Piscina Comunale a mt 500 Parcheggio Pubblico a mt 20 Richiesto supplemento per il riscaldamento  …see more

24 Photos

Monticiano / Tocchi

Tower / 1 Bedroom / sleeps 5

3 Nights min stay

Add to shortlist

from £60 / night

£416 / week

View

Key info:

  • Nearest beach 39 km
  • Suitable for children over 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Ubicato all'ingresso di un Borgo intatto del 1100 La Torre del Castello di Tocchi è diventato un appartamento su tre piani che conserva il fascino della sua storia ed il calore del passato. Il Castello di Tocchi dista solo 15' da Siena e 15' dalla bellissima ed unic  …see more

4 Photos

Province of Siena / Monticiano

Farmhouse / 2 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

from £36 / night

£247 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
Casale tipico immerso nel verde delle colline toscane. Ambiente rurale tipico a due passi dalla splendida Abbazia di San Galgano con l'autentica spada nella roccia. Possibilità di usufruire della piscina in agriturismo di lusso (ex Mulino Bianco) a circa 10 km.  …see more

8 Photos

Province of Siena / Monticiano

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £185 / night

£1295 - £2095 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Attractive old stone Tuscan villa set in private grounds with a swimming pool set amongst trees giving shade on hot summer days. Pleasant walk into the town with shops and restaurants. Sleeps 10.  …see more

38 Photos

Province of Siena / Monticiano

Villa / 14 Bedrooms / sleeps 28

7 Nights min stay

Add to shortlist

from £3182 / night

£22274 - £29701 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
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 Siena, on the top of a hill with a 360-degree view of the gently rolling Tuscan landscape. It is not just  …see more

19 Photos

Province of Siena / Monticiano

Townhouse / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £31 / night

£212 - £247 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
TOSCANA, ITALIA, SIENA, FIRENZE, VOLTERRA, CHIANTI, MAREMMA, GROSSETO, ARGENTARIO  …see more

24 Photos

Monticiano / Tocchi

Villa / 14 Bedrooms / sleeps 27

7 Nights min stay

Add to shortlist

from £1505 / night

£10529 - £20916 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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.  …see more

23 Photos

Province of Siena / Monticiano

Villa / 9 Bedrooms / sleeps 9

2 Nights min stay

Add to shortlist

from £871 / night

£6091 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
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. Our area offers breathtaking panoramas, countless daily outings and still preserves an unspoiled wilderness.  …see more

Good 3/5 

14 Photos

Province of Siena / Monticiano

House / 5 Bedrooms / sleeps 10

Good 3/5 

7 Nights min stay

Add to shortlist

from £192 / night

£1338 - £2154 / week

View

Key info:

  • Ask owner if suitable for children
  • Pets welcome
(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


16 Oct 2013

3/5

"Utter tranquility at the edge of a small, old village."

What I liked about this rental: 1. Expansive yard adjacent to wooded hills and fields. 2. The wood-fired pizza oven, which we used several times for bread, focaccia, and pizza. 3. Near to a non-tou… More

See all reviews Continue

20 Photos

Province of Siena / Monticiano

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £81 / night

£565 - £770 / week

View

Key info:

  • Ask owner if suitable for children
  • No pets allowed
(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

13 Photos

Province of Siena / Monticiano

Chalet / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £59 / night

£409 - £599 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Apartment with living-dining area, kitchen corner , double bedroom , bathroom with shower. TV SAT, iron and iron board, freezer, oven, high chair.  …see more

20 Photos

Province of Siena / Monticiano

Villa / 5 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £581 / night

£4064 - £6698 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Very stylish and beautiful villa in the heart of the famous Montalcino vine-yards. Featured in books and magazines.  …see more

24 Photos

Province of Siena / Monticiano

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £169 / night

£1183 - £2367 / week

View

Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Holiday house for 12 persons, with swimming pool , in Siena  …see more

24 Photos

Province of Siena / Monticiano

Villa / 8 Bedrooms / sleeps 18

5 Nights min stay

Add to shortlist

from £684 / night

£4784 - £5154 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • Pets welcome
Podere Monte is a luxury private Tuscany villa in the Val di Merse some 35 kilometers to the south of Siena, just north of the extensive Maremma area. The villa's building used to be an 18thbeautiful place for receiving guests. Although not as popular as other Chianti  …see more

15 Photos

Province of Siena / Monticiano

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £86 / night

£596 - £613 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Romantic hideaway in Tuscan villa with chlorine free pool. All amenities in the nearby village, walking distance. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

20 Photos

Province of Siena / Monticiano

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £90 / night

£627 - £648 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Charming and romantic hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

14 Photos

Province of Siena / Monticiano

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £90 / night

£627 - £648 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Romantic hideaway in Tuscan villa with chlorine free pool. Siena 25 minutes.All Tuscan art cities and seaside daily outings. Nature, art, peace and quiet.  …see more

20 Photos

Province of Siena / Monticiano

House / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £183 / night

£1279 - £2180 / week

View

Key info:

  • Ask owner if suitable for children
  • No pets allowed
(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

20 Photos

Province of Siena / Monticiano

House / 5 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £123 / night

£859 - £1539 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • No pets allowed
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 between Siena and Grosseto province, just 10  …see more

20 Photos

from £2936 / night

£20549 - £27398 / week

View

View

Holiday home rental

Province of Siena / Monticiano

House / 14 Bedrooms / sleeps 27

7 Nights min stay

Add to shortlist

from £2936 / night

£20549 - £27398 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
(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

24 Photos

Province of Siena / Monticiano

Farmhouse / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £119 / night

£832 - £1457 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in Monticiano with 3 bedrooms sleeps 8  …see more

48 Photos

Province of Siena / Monticiano

Villa / 9 Bedrooms / sleeps 18

2 Nights min stay

Add to shortlist

from £755 / night

£5282 - £5564 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This villa has a swimming pool in its gardens and offers accommodation for 18 guests in a building with a living room, dining area, kitchenette, bedroom and bathroom each.  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 1 Bedroom / sleeps 4

5 Nights min stay

Add to shortlist

from £51 / night

£353 - £515 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero C is a welcoming two-story apartment surrounded by the vegetation. It sleeps five people. From Casa Prospero C you will have a pleasant view of the Tuscan hills and of the surrounding countryside. Casa Prospero C is 60 square meters (645 square feet)  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 1 Bedroom / sleeps 3

7 Nights min stay

Add to shortlist

from £51 / night

£353 - £515 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero E is a graceful apartment surrounded by the vegetation. It sleeps four people. From Casa Prospero E you will have a view of the swimming pool and of the garden and of the surrounding countryside. Casa Prospero E is 100 square meters (1076 square feet)  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 2 Bedrooms / sleeps 4

5 Nights min stay

Add to shortlist

from £65 / night

£451 - £662 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero A is a pleasant and spacious apartment surrounded by meadows and by green hills. It sleeps four people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £51 / night

£353 - £515 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero B is a welcoming apartment surrounded by meadows and by green hills. It sleeps four people. It is appoximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 6 km (3  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 1 Bedroom / sleeps 3

5 Nights min stay

Add to shortlist

from £51 / night

£353 - £515 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Prospero D is a characteristic apartment surrounded by meadows and by green hills. It sleeps three people. From Casa Prospero D you will have a fascinating view of the Tuscan countryside and of the vineyards  …see more

20 Photos

Monticiano / Iesa Palazzo

Apartment / 1 Bedroom / sleeps 4

5 Nights min stay

Add to shortlist

from £51 / night

£353 - £515 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Casa Prospero F is a characteristic apartment surrounded by the vegetation. It sleeps four people. It is appoximately 100 square meters (1076 square feet)  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page