List your home
Apply filters
£ to

Holiday homes 103

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Montepulciano Clear

Location

  • All locations
  • Abbadia di Montepulciano (8)
  • Gracciano (4)
  • Sant'Albino (2)
  • Valiano (4)

more +

less -

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
Valiano
19 properties

Filters applied: Internet access (103)

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
103 Results   |  

Excellent 5/5 

45 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £31 / night

£213 - £470 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
The flat ws restored in 2001, It's about 150 mt from Piazza Grande and 30 mt from the main street. At your arrival the owner will give a free pass to enter in restricted area and to park just in front of the flat for your stay Free parking available and restricted area  …see more


13 May 2015

5/5

"Great place to launch our Tuscany vacation"

We are in the final days of our stay in Montepulciano & Tuscany. Our stay here has been nothing short of wonderful. Montepulciano has been a great location from which to take day trips throughout Tusc… More

Ciao Tom And Mary, it was a great pleasure to host you in my flat. Thanks so much. See you ciao


17 Mar 2015

5/5

"Il top della gamma a un ottimo prezzo"

Casa completamente ristrutturata, spaziosa e pulitissima, con tutti i comfort. Il proprietario è stato super disponibile e cordiale: molto flessibile con gli orari e un'ottima risorsa per buoni cons… More


29 Oct 2014

5/5

"Great Stay In Southern Tuscany"

We stayed for 5 nights in a very spacious and clean apartment. Luca was very helpful upon arrival and departure in assisting with our luggage, giving dining recommendations and making a wonderful lunc… More

See all reviews Continue

Very Good 4.5/5 

98 Photos

Province of Siena / Montepulciano

Farmhouse / 7 Bedrooms / sleeps 16

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £355 / night

£2483 - £2837 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Swimming pool 15x5mt, cleaned using salt not chlorine. 3D archery range with wild animal targets, bow rental and trainer available. Try Alessandro's traditional cousine, it will surprise you! Our cellar and vineyards are open for visit, taste our Rosso di Montepulciano  …see more


16 Aug 2014

5/5

"Perfect spot to explore Tuscany"

We arrived in three vehicles and were greeted warmly, shown through the house and then left alone to get settled in. We used the chef inspired kitchen each night - except for one when we had the host … More


13 Jun 2014

5/5

"It's like paradise!"

About 7 of us booked a four night stay at Il Molinaccio after reading the positive reviews, and we were not disappointed! Marco was very responsive whenever I had any questions and even sent me inform… More


14 Apr 2014

5/5

"Only stayed a night, wish it were a month!!""

I am not sure if it was the Tuscan air, the wonderful food, or the incredible hospitality we experinced at Il Molinaccio which I liked best! The food was local, lovingly prepared and amazing. The Tus… More

See all reviews Continue

Very Good 4.5/5 

52 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £66 / night

£461 - £532 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Ampio appartamento all'ultimo piano di palazzo d'epoca situato nel centro storico di Montepulciano. Recentemente ed elegantemente arredato con mobili d'antiquariato. Dotato di ogni comfort. 2 grandi camere,3 bagni, living, cucina attrezzata, wifi, tv digitale, ascensore  …see more


11 Sep 2014

5/5

"Perfect Base for short and longterm stays"

We rented this apartment on a long-term basis and found the experience thoroughly enjoyable. We looked at some other options, but preferred this one due to the new furniture and recent renovation. Th… More

Thanks to my first guests! I restored this apartment as if it was for me and my family. I chose the furniture that I love, all the best technological solutions to a pleasant and comfortable stay in compliance with the charm of the historic building. It's true, the view is breathtaking, the town is beautiful, a perfect solution to have a few days to relax or to explore many of the most famous places of our country; but, what can I say, I love the city where I was born. It's very nice to have others to give the same judgment!


8 Sep 2014

5/5

"Wonderful host, super clean place, very good location!"

Beautiful, clean, excellent taste in decoration, clean, super hot shower, clean, everything you need in an apartment, clean, nice view, clean again and again!!! We enjoyed this place a lot, especial… More

Thanks to this wonderful family! A young gentleman, and four lovely women, including a tender and polite "young lady"!


11 Sep 2014

4/5

"Un'insolita esperienza di soggiorno in un palazzo storico"

Ci ha particolarmente colpiti la ristrutturazione modernissima e di classe dell'appartamento immerso in un ambiente antico senza modificare lo charme che ci si aspetta da un simile palazzo storico. L… More

See all reviews Continue

Featured properties

Excellent 5/5 

19 Photos

Montepulciano / Gracciano

Apartment / 2 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £122 / night

£852 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Agriturismi nel sud della Toscana , a Montepulciano , tra la Val d'Orcia e la Valdichiana , a conduzione familiare , di piccole dimensioni ,vicino al centro storico, con vista panoramica , coltivazioni biologiche di uva , olivi , alberi da frutta IL Sorbo è assolutam  …see more


16 Feb 2014

5/5

"fantastico!"

I loved this place! beautiful landscapes. private little apartment with well stocked kitchen. Teresa was attentive to every detail and made us feel like fajmily. the location is near the town and rest… More

See all reviews Continue

Excellent 5/5 

24 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £51 / night

£355 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. T  …see more


2 Jan 2015

5/5

"Ottimo in tutto e rilassante."

Mi sono trovato benissimo e consiglierei questo incantevole agriturismo a chiunque voglia visitare le cittá del vino. Montepulciano é a 10 minuti e si raggiungono in poco tempo Montalcino, Arezzo e … More


12 Sep 2014

5/5

"Un lugar especial"

Estuvimos una semana y se hizo corta. El apartamento es precioso y está muy bien equipado. Roberta (la propietaria) nos hizo sentir como en casa con su atención y amabilidad. Fuimos con nuestro hijo… More


8 Sep 2014

5/5

"rilassante"

Ho soggiornato in questo appartamento per 3 gg. e mi sono trovato molto bene. La struttura si trova ad Acquaviva ed è a pochissimi Km da Montepulciano che con la macchina si raggiunge in 10 minuti. R… More

See all reviews Continue

Excellent 5/5 

45 Photos

Province of Siena / Montepulciano

House / 3 Bedrooms / sleeps 5

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £51 / night

£355 - £426 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Casa 5 posti letto a Montepulciano, ottima posizione panoramica sulla campagna. Circondata da uliveti. Vicinissima al Centro Storico di Montepulciano raggiungibile a piedi a circa 1 chilometro. Posto auto riservato. Caminetto, lavatrice, ampie terrazze. Riscaldamento.  …see more


15 Apr 2015

5/5

"Great view, great town!"

The villa was wonderful and so is the family renting it out. They met us at the gate and showed us around the villa and how to work everything. The mother gave us a home baked treat too! There are … More


28 Apr 2014

5/5

"Persone meravigliose e posto fantastico"

Abbiamo soggiornato per il weekend del 25 Aprile, io e la mia fidanzata, in compagnia di un altra coppia, e come benvenuto la signora Silvana ci ha accolto con un bel dolce fatto in casa...praticament… More

Gent.mo Andrea, siamo molto contente di avervi ospitato, e ci fa veramente piacere potervi avere di nuovo nostri graditi ospiti in futuro. A presto. Silvana e Virginia


24 Feb 2014

5/5

"week-end da sogno"

Ottima posizione per relax, ma al tempo stesso vicinissima al centro storico. Ottima cordialità e accoglienza dei proprietari, perfetta pulizia dell'ambiente......dobbiamo tornarci. Claudio-Gro… More

See all reviews Continue

Excellent 5/5 

22 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £63 / night

£440 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
Brand new apartment, functional, quiet, well furnished, with parking and garden, free wifi, close to the owners, close to the supermarket and at a great wine restaurant near Montepulciano, Pienza, Siena, Val d'Orcia, Cortona, Arezzo , Perugia, Assisi. Car recommended. T  …see more


8 Aug 2014

5/5

"Bellissimo"

My husband and I stayed at this beautifully renovated rental property for four nights in early May 2014. The rental's decor is lovely, and everything in it is immaculately clean and well maintained. T… More


15 Jul 2014

5/5

"A very comfortable apartment owned by friendly welcoming owners"

This our second visit to the apartment, last year we stayed in the smaller Olivio apartment next door to Cipressi. Both have been converted to comfortable living areas and have a small garden to sit i… More


7 Jun 2014

5/5

"vacanza perfetta"

L'appartamento si trova in una posizione molto comoda per visitare i dintorni, restaurato con buonissimo gusto questo casale si erge su una collina con vista splendida su Montepulciano. La proprietar… More

See all reviews Continue

Excellent 5/5 

35 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £41 / night

£284 - £497 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
A romantic, panoramic location in the heart of Montepulciano, for a delightful holiday in an ancient home in the historical centre in one of the most beautiful towns of Tuscany! Charming House in Montepulciano!  …see more


15 Apr 2014

5/5

"Wonderful apartment in a wonderful location"

We stayed at the "Notary's house" for a weekend with two small children (8 and 5). The apartment is conveniently located right in the centre of town. It has been renovated only a couple of years ago a… More

Thank you for the review about my property. The assessments correspond to the reality, in particular I believe that the location in the town, the landscape and the comfort of the apartment are the best asset for a pleasant stay.

See all reviews Continue

Excellent 5/5 

17 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £59 / night

£412 - £852 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful holiday resort near Montepulciano and Pienza  …see more


25 May 2015

5/5

"Relax e confort"

Abbiamo soggiornato in questa splendida struttura immersa nel verde e nel relax a Maggio 2015. Di solito scrivo pro e contro di ogni soggiorno, ma di contro non ne ho nessuno. Il nostro appartamento… More

See all reviews Continue

86 Photos

Province of Siena / Montepulciano

Farmhouse / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £178 / night

£1242 - £1277 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
First floor indipendent apartment. The infinity pool is sanitized using salt, far better for your skin and eyes. We are a winery where you may taste our wines,Il Golo,Rosso di Montepulciano, La Spinosa ,Vino Nobile di Montepulciano,Grappa, Finocchiaccio .and our jams  …see more

20 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

4 Nights min stay

Add to shortlist

from £48 / night

£334 - £674 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 3 Bedrooms / sleeps 8

Short stays welcome

Add to shortlist

from £84 / night

£587 - £1052 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
5-room apartment "Lecci", for 8 people, 96 m2, on the upper floor, comfortable and rustic furnishings. Living/dining room with satellite-TV and open fireplace. Smoking allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Sleepin  …see more

100 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Short stays welcome

Add to shortlist

from £77 / night

£535 - £897 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
3-room apartment "Cipresso", for 6 people, 80 m2, on the upper floor, comfortable and rustic furnishings. Living/dining room with satellite-TV and open fireplace. Smoking allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Slee  …see more

25 Photos

Province of Siena / Montepulciano

House / 3 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £152 / night

£1064 - £1383 / week

View

Key info:

  • Suitable for children over 5
  • Car advised
  • No pets allowed
CAMERE 3 POSTI LETTO 6 BAGNI 3 1/2 SAUNA CAMINO  …see more

17 Photos

Province of Siena / Montepulciano

Farmhouse / 4 Bedrooms / sleeps 8

2 Nights min stay

Add to shortlist

from £142 / night

£993 - £1135 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful country house in Tuscany, Siena  …see more

Excellent 5/5 

20 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £92 / night

£639 - £1064 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
At MOntorio is easy to arrive and difficult to live, will be your home in Tuscany. Montorio has a special and unique spot , and you will feel in love for it  …see more


1 Jul 2014

5/5

"Exactly what we were looking for"

Situated on a hill below the imposing hill which Montepulciano itself rests on, Montorio is a unit of several self-catering apartments of various sizes able to accommodate various size groups. We t… More


27 Jun 2014

5/5

"A magical setting that exceeded expectations in every way!"

My husband, 20-year-old daughter and I enjoyed 4 nights at Montorio in mid-June, 2014. We stayed in the two-bedroom, one bath unit which is spotless, very spacious and charming. The entire property is… More


30 Oct 2013

5/5

"Wonderful historic rental in heart of Tuscany"

We spent a week in the studio apartment in October. It was great! The buildings are a remodeled convent or something--thick walls, tile floors, beautiful. The apartment is larger than we expected--… More

See all reviews Continue

24 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £1479 / night

£10348 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin.  …see more

Excellent 5/5 

22 Photos

Montepulciano / Gracciano

Cottage / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £67 / night

£469 - £688 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This charming rural cottage is a converted farm building in the heart of the countryside near Montepulciano. It is ideally situated with its own private garden space surrounded by hills and vineyards, where guests can relax and enjoy the peaceful surroundings. It is  …see more


28 Apr 2015

5/5

"Pefect place for family holidays"

We spent wonderful week in this place. The host was nice and warm, trying to help in any case we asked. Clean and in very good condition house, suits perfectly to all you may need during holiday. Very… More


5 Jul 2014

5/5

"AWESOME PLACE, HIGHLY RECOMMENDED!"

We stayed in Agriturismo Il Salarco for one week the end of July. It is an amazing place, great location, close to Montepulciano, Pienza and Sienna. The house is very clean, nice comfortable beds an… More


23 May 2013

5/5

"Excellent centre for exploring Umbria and Tuscany"

We stayed in the studio apartment. The standard and quality of the accommodation was excellent and the support and helpfullness from Laura could not have been better. In an hour you can be in Fl… More

See all reviews Continue

4 Photos

Montepulciano / Gracciano

House / 4 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £36 / night

£249 / week

View

Key info:

  • Nearest beach 200 km
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Cas colonica immersa nella campagna toscana con possibilità di escursioni, itinerari turistici ed enogastronomici, soggiorni nelle terme vicine di Rapolano e Bagnovignoni. Escursioni e visite dei siti della Val D'orcia e dei siti Etruschi di Chiusi.  …see more

Excellent 5/5 

21 Photos

Province of Siena / Montepulciano

Cottage / 3 Bedrooms / sleeps 5

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £41 / night

£284 - £497 / week

View

Key info:

  • Nearest beach 158 km
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Independent villa with garden and exclusive parking. Immersed in the Tuscan countryside just 5 minutes walk from the center of Montepulciano, from the bus station and supermarket. Air-conditioned rooms with free use of wi-fi. Close to Val D'Orcia Cortona Pienza Siena.  …see more


29 Jun 2015

5/5

"Tuscany farmhouse was wonderful"

My wife and I were absolutely thrilled with the county cabin near Montepulciano. Davide was a fantastic host and recommended some great restaurants and day trips. He and his father have beautifully … More

Many thanks for all, it was very nice to meet you! I hope to see you soon! Davide


25 Mar 2015

5/5

"Amazing…absolutely breathtaking!"

I can't say enough about how amazing our stay was at La Casina Toscana. My boyfriend and I both had an amazing time here and both agreed it was the highlight of our 2 week vacation in Europe. The hous… More

Thanks guys, you've been very kind! I will be very happy to welcome you again, maybe together with your families! See you soon and thanks again for everything! Davide


4 Jun 2015

5/5

"Everything we had hoped for"

La Casina Toscana is a beautiful villa nestled in the hills of Montepulciano, furnished with charm and character. It had all the amenities we needed and was a lovely retreat from the craziness of Ven… More

Many thanks for all, it was very nice to meet you! I hope to see you soon! Davide

See all reviews Continue

Very Good 4.5/5 

23 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 4

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £56 / night

£391 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
montepulciano casa vacanze giardino relax pienza A pochi kilometri si trova il centro Termale di Montepulciano, e le terme sensoriali di chianciano terme  …see more


13 May 2015

5/5

"Loved our Apartment in Montepulciano - Perfect location"

We had such a wonderful stay at the Garden House. Antonella and her husband where lovely. Antonella english is excellent and she was able to help us with whatever questions we had. We rented the… More


18 Feb 2015

5/5

"Ottima Sorpresa"

A pochi passi dal centro di montepulciano abbiamo soggiornato in questo grazioso appartamento davvero molto confortevole. Ottima pulizia, arredamento di gusto e letto davvero davvero molto comodo! A d… More


23 Mar 2015

4/5

"Excellent for families - in the core of Montepulciano old town"

It was a lovelly stay in Garden House Montepulciano. Antonella is a very nice hostess, we really stayed well there. The apartment is nice, well furnished, very cosy place just a few steps from everyth… More

See all reviews Continue

Excellent 5/5 

24 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £61 / night

£425 - £1028 / week

View

Key info:

  • Nearest beach 170 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Shining, fresh, large and modern 2 bedroom apartment . You can easily access to the historic part of Montepulciano and its old style and art shops, monuments and churches (100mt.). Also very close to all of the others Montepulciano 's facilities. In the core of Tuscany  …see more


2 Apr 2015

5/5

"Classy Apartment lwell located"

We fell in love with the town, the apartment and the people here. The host, his friends & family were most gracious. It made our stay here extra special because of all their care and attention to det… More

Many thanks for your beautiful review! I have been very glad to host you and your lovely family! Wish you all the best and see you soon!!!


17 Mar 2015

5/5

"Appartamento Accogliente"

L'appartamento si trova a 500mt dalla porta principale dalla quale si accede al centro storico di Montepulciano. Si trova al primo piano , è stato ristrutturato ( molto bene ) da forse due anni. Gli … More

Grazie mille di tutto! E' stato un piacere accoglierla e mi dispiace solo che all'inizio non trovava la via ed eravate stanchi dopo il viaggio lungo. Alla fine e' stato un piacere ritrovarsi al bar in fronte e prendere una cosa insieme li. Grazie ancora!


10 Mar 2015

5/5

"Incantevole"

Incantevole appartamento!!! Tutto nuovo, moderno e giovanile, molto accogliente e arredamento curato nei minimi particolari. Degna di nota è l'eccellente pulizia cosa che ho notato subito! Ha due … More

Grazie davvero di tutto! È stato un piacere ospitarvi, siete statiolto gentili e rispettosi. Un abbraccio e a presto.

See all reviews Continue

Very Good 4/5 

10 Photos

Province of Siena / Montepulciano

Guest house / 1 Bedroom / sleeps 2

Very Good 4/5 

1 night min stay

Add to shortlist

from £82 / night

£568 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
the romantic Galletto's house make part of Podere Benefizio . It,is very romantic with the fireplace, the old stones and wood and a wonderful view. It's indipendent from the main farmhouse, with garden, parking and a big veranda with barbecue. Near Pienza, Chianciano  …see more


15 Jul 2015

4/5

"Fun in a one-bedroom cottage in Tuscany"

We enjoyed 5 nights here on our 2 week trip to Italy. It was so nice having a kitchen and room to spread out, but don’t expect to be able to walk to the supermarket, restaurants or Montelpulciano. T… More

See all reviews Continue

Excellent 5/5 

6 Photos

Montepulciano / Valiano

House / 1 Bedroom / sleeps 2

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £31 / night

£213 - £284 / week

View

Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car essential
  • Air conditioning
  • Pets welcome
Il Grottino è un delizioso terratetto, ristrutturato nel tipico stile toscano. Situato nel centro storico della piccola e tranquilla Valiano (Montepulciano), si tratta di un luogo strategico a pochi chilometri dalle principali mete turistiche di Toscana e Umbria.  …see more


17 Nov 2014

5/5

"Fantastic place for a couple in a wine paradise"

Very nice, cosy and romantic small house in a very small town of Valiano in the heart of Val d'Orcia. Strongly recommended for couples loving adventures. Not more than for two persons! The car is ess… More


7 Jan 2015

5/5

"Comodo e familiare"

Ho alloggiato due notti presso la Residenza il Grottino; avevo intenzione di trascorrere un week end tranquillo con la mia ragazza nell'area di Montepulciano, e alla fine ho scelto di soggiornare in q… More


5 Jan 2015

5/5

"Una vacanza perfetta"

Sono stato insieme alla mia ragazza in vacanza in questa struttura a cavallo di capodanno. Che dire, il rapporto qualità prezzo è impressionante, nell'abitazione non sono riuscito a trovare una manc… More

See all reviews Continue

16 Photos

Province of Siena / Montepulciano

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £244 / night

£1703 - £2121 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Luxury villa, en-suite marble bathrooms, private pool, amazing views on Montepulciano, perfect for wine tours of Vino Nobile wines  …see more

21 Photos

Province of Siena / Montepulciano

Townhouse / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £51 / night

£355 - £653 / week

View

Key info:

  • Suitable for children over 5
  • No pets allowed
f  …see more

21 Photos

Montepulciano / Valiano

Villa / 8 Bedrooms / sleeps 20

Short stays welcome

Add to shortlist

from £456 / night

£3192 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa located on top of a hill and dipped between wineyards. Due to its strategic position, in Valiano di Montepulciano, half way from Rome to Florence and on the border between Tuscany and Umbria region, it will be easy to visit the most artistic towns in Italy  …see more

14 Photos

Province of Siena / Montepulciano

B&B / 4 Bedrooms / sleeps 9

3 Nights min stay

Add to shortlist

from £467 / night

£3263 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Palazzo Nobile di San Donato is a luxury bed and breakfast and residenza d'epoca, period house set in an ancient medieval noble “tower house” in Montepulciano Historical centre, Tuscany can be rented for groups of 8/9  …see more

15 Photos

Province of Siena / Montepulciano

B&B / 3 Bedrooms / sleeps 9

3 Nights min stay

Add to shortlist

from £112 / night

£781 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
b&b nella campagna di Montepulciano, Punto strategico per visitare sia la Toscana che l'Umbria.  …see more

9 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

Min stay varies

Add to shortlist

from £41 / night

£284 - £320 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
ersonal check in and check out, guests will have my mobile telephone number for any possible further assistance required. I can organize wine tours , tuscan cookery courses , horse riding. A full brochure describing all local activities is provided upon arrival . st  …see more

6 Photos

Province of Siena / Montepulciano

Guest house / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £51 / night

£355 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Altes restauriertes Landhaus  …see more

10 Photos

Montepulciano / Abbadia di Montepulciano

B&B / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £57 / night

£398 - £497 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Agriturismo natura terme ristorante montepulciano pienza famiglia cortona affitto vespe campagna relax vino enogastronomia zafferano prodotti tipici Marmellate confetture toscana outlet val di chiana val d'orcia lago  …see more

24 Photos

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 12

4 Nights min stay

Add to shortlist

from £249 / night

£1738 - £3171 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Nearby there are others agreeable towns like Pienza, Cortona, San Quirico d'Orcia, making it an ideal destination from which to savor the full essence of Tuscany. All around the villa an enchanting garden equipped with gazebo, table and chairs, the swimming pool  …see more

6 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £51 / night

£355 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Struttura situata a 2 km dal centro storico di Montepulciano, situata su una collina con vista diretta sul paese e sulle vigne dalle quali viene prodotto il vino nobile di Montepulciano e sulla Valdichiana. Oltre al giardino interno recintato è presente anche un piccol  …see more

6 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £102 / night

£710 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Splendida ubicazione, vicinanza ai parcheggi, estremamente luminoso con affaccio sulla campagna. Silenziosissimo, pur essendo ubicato nel centro del paese le nuovissime finestre isonorizzate lo rendono estremamente silenzioso.  …see more

Very Good 4/5 

25 Photos

Province of Siena / Montepulciano

Apartment / 1 Bedroom / sleeps 2

Very Good 4/5 

1 night min stay

Add to shortlist

from £50 / night

£348 - £518 / week

View

Key info:

  • Nearest beach 185 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Pets welcome
In the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history, art, architecture and the Nobile wine, lays this small hamlet made of country houses built in bricks and local stones. Its origin dates back to the end of t  …see more


14 Oct 2012

4/5

"Wow! A relaxing well appointed holiday home"

This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a … More

See all reviews Continue

Excellent 5/5 

23 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £66 / night

£461 - £639 / week

View

Key info:

  • Nearest beach 185 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • Pets welcome
In the magnificent atmosphere of the hills surrounding the ancient town of Montepulciano, famous for its history, art, architecture and the Nobile wine, lays this small hamlet made of country houses built in bricks and local stones. Its origin dates back to the end of t  …see more


31 Oct 2013

5/5

"Stunning estate and perfect location"

I went with by partner in June for a 5 night stay after a couple nights in Florence. It was the perfect holiday and this appartment was exactly what we wanted - somewhere quiet, with a pool and close… More


13 Jul 2013

5/5

"Return visit"

One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are … More


31 May 2013

5/5

"Amazing apartment and view"

My husband and I stayed in apartment #5 for four nights and absolutely fell in love. It was such a beautiful apartment with all the amenities that you would want. It was beautifully decorated. We l… More

See all reviews Continue

Excellent 5/5 

8 Photos

Province of Siena / Montepulciano

House / 2 Bedrooms / sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £102 / night

£710 - £852 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Two Bedroom Ground Floor Apartment Montepulciano Fontana della Quercia is a charming apartment in a pretty farmhouse situated on a beautiful estate with unspoilt views of vineyards and olive groves all around. The apartment is extremely tastefully furnished in exquis  …see more


20 Aug 2013

5/5

"Fantastic Tuscan vacation!"

Thank you very much. Everything was great & the service fantastic. The property is beautiful. The rooms well kept. Location is close to everything. We especially liked Cortona. We really enjoyed our s… More

See all reviews Continue

24 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £355 / night

£2483 - £4876 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Biagio is situated close to the hilltop town of Montepulciano renowned for its historical importance and for its wine Nobile. This magnificent country house is one of the most exclusive and stunning farmhouses in the area. It can accommodate up to 16 persons!  …see more

19 Photos

Province of Siena / Montepulciano

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £198 / night

£1383 - £3298 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Elegant air-conditioned villa with private pool to rent close to Montepulciano – sleeps 8 From 2300€ to 4650€ a week  …see more

34 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £254 / night

£1773 - £4255 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Beautiful stone-built villa rental that has been completely renovated and transformed into a comfortable, exclusive holiday residence, situated near Montepulciano in the beautiful Tuscan countryside. This area of the countryside is, for the most part, made up of the vin  …see more

20 Photos

Province of Siena / Montepulciano

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £193 / night

£1346 - £2552 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa for rent situated inside a farm just outside the town of Montepulciano, in the hills south of Siena, Tuscany. Located on a hillside, the villa has a breathtaking view of the vineyards that produce Vino Nobile di Montepulciano, one of the wines that makes the Itali  …see more

24 Photos

Montepulciano / Abbadia di Montepulciano

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £137 / night

£958 - £1667 / week

View

Key info:

  • Nearest beach 201 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Pets welcome
Villa Abbadia is an ancient country house located in the village of Abbadia di Montepulciano about 10 km from Montepulciano. The villa, nearly completely made in red bricks, preserves many typical Tuscan traditional features such as the terracotta floors and wooden be  …see more

7 Photos

Province of Siena / Montepulciano

House / 1 Bedroom / sleeps 2

7 Nights min stay

Add to shortlist

from £71 / night

£497 - £639 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
One Bedroom Ground Floor Cottage Montepulciano Southern Tuscany L' Antico Forno is a charming detached cottage situated on a beautiful estate with unspoilt views of vineyards and olive groves all around. The cottage is very tastefully furnished and fitted in exquisite  …see more

Very Good 4.5/5 

22 Photos

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 15

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £405 / night

£2830 - £4574 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Wine lovers will find much to appreciate at Villa Montepulciano. Located on an estate that still produces boutique wines and olive oils, the villa offers guests the chance to taste wines grown just outside. Six bedrooms, divided between a main house and guest cottage, o  …see more


20 Jul 2013

5/5

"Perfect..."

Perfect Villa and setting to enjoy all the splendors that Tuscany and Montepulciano has to offer. - Rose L., ,… More


20 Dec 2013

4/5

"Our Stay at Villa Montepulciano"

We had a great time and loved using th evilla. It was a lot of fun.… More

See all reviews Continue

13 Photos

Province of Siena / Montepulciano

Villa / 6 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £760 / night

£5320 - £6504 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
If your dream of a Tuscan vacation includes views of rolling green hills, rustic stone architecture and dining on local produce every day, villa Penelope is a dream come true. The renovated six-bedroom stone farmhouse, set on a hilltop just outside Montepulciano, has go  …see more

16 Photos

Province of Siena / Montepulciano

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £597 / night

£4174 - £4375 / week

View

Key info:

  • Not suitable for children
  • Pets welcome
Situated at a 20 minutes drive from Cortona and 10 minutes from Montepulciano, this luxurious villa is an ideal solution for those who love having half day tours in the most famous Tuscan cities. Set in the beautiful and unique Val di Chiana countryside, the villa is ea  …see more

21 Photos

Province of Siena / Montepulciano

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £275 / night

£1925 - £3453 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Villa Pulce is a recently restored farmhouse which offers breathtaking views over the valley where Vino Nobile of Montepulciano is produced. The villa is situated in one of the most beautiful and panoramic hill around the town of Montepulciano and it is ideal for a comf  …see more

15 Photos

Montepulciano / Valiano

Villa / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £228 / night

£1595 - £3120 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer's family who lived there until the early '70s. The ground floor of the main house was used for storage while cattle were tethered in the vaulted  …see more

18 Photos

Montepulciano / Sant'Albino

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £264 / night

£1842 - £2552 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
La Cantina Villa for rent with swimming pool in Montepulciano  …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