List your home
Apply filters
£ to

30 Holiday homes in Montepulciano

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
Rome
2,491 properties
Florence
966 properties
Trapani
517 properties
Venice, Veneto
501 properties
Amalfi Coast
463 properties
Lucca
431 properties
Cortona
430 properties
Palermo
399 properties
Sorrento, Campania
353 properties
Cefalu
317 properties
San Gimignano
297 properties
Taormina
269 properties
Greve in Chianti
268 properties
Syracuse
257 properties

Filters applied: City breaks (30)

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
30 Results  |  
24 Photos

Farmhouse | 7 Bedrooms | sleeps 16

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £364 /night

£2544 - £3901 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

23 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £76 /night

£530 - £944 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
2 bedroom beautiful 500 year old restored farmhouse. 7km outside of Montepulciano. Pool, terrace, garden area, patio, and BBQ. 5 minute drive to nearest supermarket, shops, bars and restaurants.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £68 /night

£475 - £586 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
The estate is near to other historical place, like Orvieto, Pienza, Arezzo, Siena, Florence , Rome. http://www.airport.umbria.it/en Ideal place to relax , in the middle of an agricultural estate were we produce wines red and white and oil.  …see more

Featured properties

13 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £76 /night

£528 - £776 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
“Casa al bosco” is an elegant house restored in the second half of the 1800s. It is situated in a property of approximately 12 hectares where there are olive trees and a vineyard.  …see more

24 Photos

Farmhouse | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £194 /night

£1357 - £1527 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Wonderful place to relax, make sports ( walking,archery and swimming) sip our good wine and enjoy our cousine. Our swimming pool is 15x5mt wide and is cleaned using salt and not chlorine.  …see more

11 Photos

Apartment | 3 Bedrooms | sleeps 6

Very Good 4.5/5 

5 Nights min stay

Add to shortlist

from £62 /night

£432 - £784 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
The large apartment (116 sqm) is situated in the historical centre of Montepulciano. Inside the house the guests will appreciate its peaceful and warm atmosphere. The apartment has been recently restored with the intention of giving its guests the best comfort.  …see more

21 Photos

Castle | 6 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £412 /night

£2880 - £3080 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Romantic castle with pool to rent near Montepulciano – sleeps 14+2 From 3300€ to 3850€ a week  …see more

16 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £79 /night

£550 - £780 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Beautiful brick farmhouse built in the XVIII century. It is plunged into the peace of a sweet Tuscan hill, on the border between Tuscany and Umbria. It has been built in the respect for the old architecture and tastefully furnished with the family valuable furniture.  …see more

12 Photos

Farmhouse | 9 Bedrooms | sleeps 20

7 Nights min stay

Add to shortlist

from £229 /night

£1600 - £3280 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Antique farmhouse with two floors and two outbuildings, which was recently renovated into a more than 100 hectares with wine grounds and olive groves. In the maintained and private garden guests will find a beautiful and panoramic swimming pool.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £256 /night

£1792 - £3360 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Pietra del Diavolo, recently renovated, is located on one of the most panoramic hills around Montepulciano. Its name comes from the place where it was built on a base that is very rocky and mainly composed of layers of tuff  …see more

11 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £37 /night

£255 - £594 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
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

18 Photos

Apartment | 2 Bedrooms | sleeps 6

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £67 /night

£467 - £721 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Located in a wonderful area, along the wine road that leads from Montepulciano to Pienza, sorrounded by vineyards, olive trees, fields, woods. we offer self catering apartments , and also B&B service . new airport at 30 Km distance http://www.airport.umbria.it/en ASK AVAILABILITY we have apartment 4 people located in rustic farmhouses  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £219 /night

£1527 - £2968 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The place is peaceful, outside in the garden; you have the possibility to relax under the trees or to eat under the stars. Beautiful structure for a relaxing holiday in the tuscany area . ask for availability we have several solution for you. also self catering apartments with breakfast service.  …see more

24 Photos

Guest house | 7 Bedrooms | sleeps 14

Short stays welcome

Add to shortlist

from £606 /night

£4240 - £6106 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa in the historical and cultural heart of Tuscany near the centre of Montepulciano, with restaurant, market and cafe/bar, all at our door step. We offer Internet connection, buffet breakfast, dinner in private terrace, wine tour, Jacuzzi and a wanderfull gaden. Ardene provides its guests with a high standard of accommodation. The private swimmingpool is wonderful!  …see more

20 Photos

House | 3 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £67 /night

£467 - £509 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
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. Montepulciano è punto di partenza per visitare tante città d'arte: Pienza,Siena,Perugia, Arezzo,Firenze ecc.  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £146 /night

£1018 - £1357 / week

View

Key info:

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

19 Photos

Apartment | 2 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £49 /night

£340 - £1272 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Agriturismo 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 assolutamente indipendente e gode di una splendida vista sulla tipica campagna toscana  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £61 /night

£424 - £594 / week

View

Key info:

  • Nearest beach 158 km
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villetta indipendente con giardino e parcheggio esclusivi. immersa nel verde della campagna toscana a soli 5 minuti a piedi dal centro storico di Montepulciano, dall'autostazione e dal supermercato. Camere climatizzate con uso gratuito della connessione internet wi-fi. Interni in autentico stile toscano: travi in legno, nicchie e l'antico focolare caratterizzano la struttura.  …see more

22 Photos

Apartment | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £59 /night

£408 - £526 / week

View

Key info:

  • Suitable 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. There is NO swimming pool in the house, but nearby there are swimming pools, spas and natural hot springs.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £51 /night

£357 - £424 / week

View

Key info:

  • Suitable 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. There is NO swimming pool in the house, but nearby there are swimming pools, spas and natural hot springs.  …see more

14 Photos

Condo | 5 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £152 /night

£1060 - £1272 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Appartamento Attico Mansarda a Montepulciano Centro Storico, completamente autonomo. Grandi spazi sia nelle camere che nei due salotti. Cucina con tinello/pranzo con grande tavolo e tutto il necessario per 10/12 ospiti, completamente fornita di stoviglie,2 frigoriferi.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £49 /night

£340 - £382 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
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 Su prenotazione: servizio di breakfast cene con i piatti della tradizione corsi di cucina servizio taxi  …see more

24 Photos

B&B | 6 Bedrooms | sleeps 12

1 night min stay

Add to shortlist

from £66 /night

£458 - £764 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
Toscan,Montepulciano,lago di Montepulciano,vacanze in Toscana,appartamenti in Toscana,piscina,cavalli,natura,holiday vacantion Tutti i nostri appartamenti -suite sono dotati di idromassaggio,letti a baldacchino,salotti con angoli cottu  …see more

15 Photos

B&B | 3 Bedrooms | sleeps 9

Min stay varies

Add to shortlist

Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
b&b nella campagna di Montepulciano, Punto strategico per visitare sia la Toscana che l'Umbria.  …see more

5 Photos

House | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £37 /night

£255 / week

View

Key info:

  • Not suitable for children
  • Pets welcome
Piccola, accogliente, centrale e dotata di ogni comfort  …see more

5 Photos

B&B | 4 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £146 /night

£1018 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Agriturismo biologico, bed and breakfast,fattoria biologica, cucina vegetariana e vegana,  …see more

12 Photos

B&B | 13 Bedrooms | sleeps 25

1 night min stay

Add to shortlist

from £51 /night

£357 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Immerso nel verde gode di un incantevole e panoramica posizione con vista sulla Valdichiana.Offre sistemazione in spaziose camere, con bagno privato e balcone, tv, telefono, aria condizionata, asciugacapelli, wi-fi gratuito, quasi tutte con vista panoramica. Per i nostri clienti sconti per le Terme di Montepulciano e Chianciano,  …see more

9 Photos

Apartment | 1 Bedroom | sleeps 2

Min stay varies

Add to shortlist

from £55 /night

£382 - £543 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Apartment located in a very green and quiet area just few meters form the old town centre of Montepulciano, the ideal place to relax beeing in contact with the nature. Free wifi connection, garden, swimming pool, jacuzzi  …see more

11 Photos

Farmhouse | 4 Bedrooms | sleeps 13

Min stay varies

Add to shortlist

from £158 /night

£1103 - £1442 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Ski
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Tipico casale toscano immerso nel bosco di Montepulciano (SI) con vista su vallata, bosco, colline toscane e lago. Dista soli 6 km. dal centro storico di Montepulciano (SI) noto per le sue magnifiche bellezze artistiche e storiche. Possibilità di avere disponibilità di personale dei servizio, baby sitter, nolo bici, equitazione.  …see more

5 Photos

Farmhouse | 1 Bedroom | sleeps 2

Min stay varies

Add to shortlist

from £110 /night

£764 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
The Country House Ardene provides its guests with high level services in a magical, peaceful and unforgettable atmosphere. All the apartments and some rooms are equipped with whirlpool bath, air conditioning, satellite tv, internet connection. The exclusive outdoor swimming pool offers our guests unforgettable moments of relax.  …see more