List your home
Apply filters
£ to

27 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
2,531 properties
Florence
986 properties
Trapani
505 properties
Venice, Veneto
498 properties
Amalfi Coast
470 properties
Lucca
438 properties
Palermo
423 properties
Cortona
419 properties
Sorrento, Campania
350 properties
Cefalu
314 properties
San Gimignano
300 properties
Greve in Chianti
276 properties
Taormina
275 properties
Alghero
260 properties

Filters applied: Air conditioning (27)

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
27 Results  |  
17 Photos

Apartment | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £45 /night

£314 - £679 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Pets welcome
holiday resort located in the middle of a vine yard, few minutes from Montepulciano. Excellent wine for tasting  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

4 Nights min stay

Add to shortlist

from £54 /night

£374 - £806 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • 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

20 Photos

Farmhouse | 1 Bedroom | sleeps 3

3 Nights min stay

Add to shortlist

from £119 /night

£832 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
Apartment located inside an Agriturismo in Montepulciano Tuscany. The apartment has a double room, a kitchen, a dining room with Fireplace and a private batrhoom with Jacuzzi. Available to clients: Private Parking, Gazebo and Swimming Pool.  …see more

Featured properties

4 Photos

B&B | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £72 /night

£499 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
ROOM: Double Room FACILITIES: Plasma Tv, Satellite Decoder Hairdryer, Minibar, Air Conditioning, Heating BATHROOM: Private Bathroom with Shower ROOM SIZE: 21 square meters SHARED AREAS: Private Parking, Gazebo, Swimming Pool  …see more

9 Photos

Farmhouse | 9 Bedrooms | sleeps 22

1 night min stay

Add to shortlist

from £85 /night

£594 - £4156 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful estate were you can have organize a holiday in a private structure or bed and breakfast service.  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £223 /night

£1560 - £3000 / 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 6 From 2160€ to 3480€ a week  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £500 /night

£3500 - £5500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Biagio is situated close to Montepulciano. This magnificent country house is known for being the most exclusive and stunning farmhouse you can find in this area. It is the perfect choice if you are looking for a peaceful and relaxing holiday.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £218 /night

£1520 - £2880 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …see more

22 Photos

Cottage | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £37 /night

£255 - £823 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages 5
  • 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 also only a few minutes away from the shops, restaurants and bars of the nearby villages.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 23

7 Nights min stay

Add to shortlist

from £546 /night

£3816 - £5936 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …see more

12 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £388 /night

£2712 - £3992 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Podere Montepulciano sits on a hill just ten minutes drive away from captivating Renaissance town Pienza.  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Short stays welcome

Add to shortlist

from £226 /night

£1578 - £2905 / week

View

Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Due to the central geographical position of Villa Pietra del Diavolo you can spend a day touring famous cities rich in history, culture, architecture and artistic works such as Siena (km 45), Arezzo (km 50), Firenze (km 110), Perugia (km 70), Roma (km 150). Croce di Febo take care of our land according to the traditions of organic agricolture respecting the soil.  …see more

20 Photos

Villa | 12 Bedrooms | sleeps 24

7 Nights min stay

Add to shortlist

from £2160 /night

£15120 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
  • Private garden
The villa is elegant and majestic in its eighteenth century form, the location is stunning with excellent furnishing and a beautiful garden, a welcoming and cozy atmosphere in a perfect Italian style Villa.  …see more

16 Photos

Villa | 9 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £16250 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annex. It is surrounded by breathtaking views over the Italian countryside  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £522 /night

£3648 - £4576 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
A stunning residence built into the ancient city walls of the medieval and atmospheric town of Castelmuzio, BORGO ANTICO is the epitome of style and grace. Situated in the tiny but charming Piazza San Bernardino in the town's historic center  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 18

2 Nights min stay

Add to shortlist

from £1179 /night

£8250 - £16250 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
The exquisite villa is located in Contignano surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms, 2 twins, 5 doubles and a lofted bedroom containing a sofa bed, a twin and a double bed  …see more

22 Photos

Villa | 6 Bedrooms | sleeps 12

rentals_reviews_rating_2 

2 Nights min stay

Add to shortlist

from £497 /night

£3473 - £5119 / week

View

Key info:

  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
Six bedroom historical villa in the countryside of Montepulciano, a vibrant city at the heart of the Siena region of Tuscany.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £400 /night

£2800 - £3200 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
Wonderful Tuscany villa near Montepulciano with private pool and air conditioning for 10 people.  …see more

7 Photos

Hotel apartment | 7 Bedrooms | sleeps 22

1 night min stay

Add to shortlist

from £97 /night

£679 - £4156 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
  • Private garden
It is the second structure that we have opened. Half way up the main street of Montepulciano, a few meters from Piazza delle Erbe and the Tower of Pulcinella, “La Dimora” provides large space and is equipped with every comfort, air conditioning and Wi-Fi included. On t  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £61 /night

£424 - £1272 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

Add to shortlist

from £146 /night

£1018 - £1357 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful country house in Tuscany, Siena  …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
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

23 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £49 /night

£340 - £509 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Casa indipendente con ampio giardino esterno, vicinissima al centro storico di Montepulciano, ma allo stesso tempo in piena campagna.  …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

24 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £66 /night

£458 - £653 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
Appartamento 4 persone (due in letto matrimoniale, due su divano-letto). Arredato con cura ed eleganza, con servizi privati e cucina autonoma con forno e frigorifero, tv lcd satellitare, riscaldamento autonomo a gas, aria condizionata, camino a legna, biancheria  …see more

10 Photos

Villa | 13 Bedrooms | sleeps 27

2 Nights min stay

Add to shortlist

from £85 /night

£594 - £764 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
E' possibile gustare la squisita cucina locale e nel contempo immergersi nella cultura artistica di Siena e della vicina Firenze o semplicemente in "un dolce far niente". Tutto questo è "Casa al Bosco", luogo ideale per chiunque voglia vivere una vacanza all'insegna del  …see more

5 Photos

Apartment | 2 Bedrooms | sleeps 7

Excellent 5/5 

Min stay varies

Add to shortlist

from £170 /night

£1188 / week

View

Key info:

  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
  • Private garden
apartments Montepulciano, accommodation Montepulciano, Holiday rental tuscany, tuscan Holiday, In the historical center of Montepulciano, apartments have a kitchen - living room and one to three bedrooms  …see more