List your home
Apply filters
£ to

116 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
2,424 properties
Florence
949 properties
Trapani
499 properties
Venice, Veneto
481 properties
Amalfi Coast
457 properties
Cortona
428 properties
Lucca
428 properties
Palermo
383 properties
Sorrento, Campania
350 properties
Cefalu
310 properties
San Gimignano
296 properties
Greve in Chianti
267 properties
Taormina
261 properties
Syracuse
250 properties

Filters applied: Non-Smoking property (116)

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
116 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
  • Suitable for children of all ages
  • 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

23 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £61 /night

£424 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
we rent house in center of Montepulciano. Flat (apartment) of roughly 60 sq m (646 sq ft), located in via Cagnano 9. Restored in 2011 it is has high quality finishes and exposed beams. It consists of a large living room/kitchen, two bedrooms (one of which is a master b  …see more

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

Featured properties

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

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £57 /night

£396 - £565 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
Farmhouse apartment with seasonal outdoor pool, in Montepulciano Tuscany country estate surrounded with the wonderful Nobile-Vineyards.  …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

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

Farmhouse | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £61 /night

£424 - £509 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
single room in a Villa with only 7 rooms. Infinity pool sanitized using salt and not chlorine, far better for your skin and eyes. We are a winery where you may visit our cellar and taste our wine,Il Golo,Rosso di Montepulciano DOC, Grappa, Finocchiaccio and marmelades.  …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
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
holiday apartments in Montepulciano. Farm stay in a wine estate in Montepulciano  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 4

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £97 /night

£679 - £806 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Valiano is not so far from Arezzo, Perugia and Siena, nearby you can find Spa or nice villages. In Summer there are festivals and others kind of music intertainements around here.  …see more

17 Photos

B&B | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £61 /night

£424 / week

View

Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Every morning the lady of the house makes amazing and always new breakfasts, created with the genuine products of the area and with a deep experience of cooking. Gluten intolerant breakfast. Please notify us in advance.  …see more

15 Photos

Watermill | 6 Bedrooms | sleeps 12

3 Nights min stay

Add to shortlist

from £146 /night

£1018 - £2248 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Beutiful old structure located in one of the most unspoiled place of the area. this Villa , with two annex one just adjacent , the second at 100 meters , is ideal for family or friends groups.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £106 /night

£738 - £1272 / week

View

Key info:

  • Suitable 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

21 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £400 /night

£2800 - £3800 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £120 /night

£840 - £1200 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
This little, two-storey, converted Tuscany farmhouse has been meticulously restored in a simple, rustic style, employing high-quality traditional materials.  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £86 /night

£600 - £784 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
I Tigli is a splendid apartment with two bedrooms and two bathrooms which is part of a property with a total of 6 apartments sharing a pool.  …see more

23 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £286 /night

£2000 - £4800 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves.  …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
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

22 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £218 /night

£1520 - £2880 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano.  …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

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

8 Photos

Apartment | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £72 /night

£504 - £720 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
TV, iron and iron board, freezer, oven, high chair, facilities for disabled.  …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

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
  • Suitable for children of all ages
  • 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

9 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £60 /night

£414 - £631 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
Guests will find inspiring spaces for reading and relaxing, a beautiful swimming pool, a panoramic terrace, solarium, barbeque and a bread-oven with covered area. Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £73 /night

£509 - £755 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
It's composed from a stay- kitchen with read couch and fire place, two double bedrooms and a big bath with double console and Jacuzzi. In the stay-kitchen: tv sat. Guests can purchase Vino Nobile di Montepulciano and Extra Virgin Olive Oil from the farm  …see more

17 Photos

Guest house | 7 Bedrooms | sleeps 16

1 night min stay

Add to shortlist

from £77 /night

£535 - £713 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
There is something that suits everybody's fancy!  …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

12 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £252 /night

£1760 - £3040 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Luxury Tuscan farmhouse and private pool, with stunning views over Montepulciano 4 double bedrooms all with en-suite marble bathrooms  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £200 /night

£1400 - £2320 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Unique villa with swimming pool.  …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

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

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

7 Photos

B&B | 6 Bedrooms | sleeps 15

1 night min stay

Add to shortlist

from £63 /night

£441 - £2968 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Bed and breakfast, rooms in this small and familiar structure are equipped with every comfort including breakfast buffet and Wi  …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:

  • Suitable for children of all ages
  • 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

18 Photos

Farmhouse | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £58 /night

£400 - £560 / week

View

Key info:

  • Nearest beach 106 km
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
The apartment has two bedrooms one big bathroom and a service bath.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £271 /night

£1896 - £3708 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
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.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £272 /night

£1900 - £3600 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Positioned on a hilltop, theandnbsp;Villa Pietraandnbsp;is the most fabulous panorama beauty. It gives the sensational and arresting view of the valley where the famous "Nobile di Montepulciano" wine is created. The very look of the villa gives an impression of  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £80 /night

£560 / week

View

Key info:

  • Nearest beach 120 km
  • Suitable for children of all ages
  • No pets allowed
These quaint apartments are perfect for guests who want a holiday full of complete relaxation, while enjoying terrific views of Montepulciano and the surrounding valley. It is in the perfect location to discover the cultural and historical heritage o  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £96 /night

£672 - £784 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Palazzoandnbsp;Apartment inandnbsp;Montepulciano Italyandnbsp;is distinctly raunchy and practically chic in its own way.andnbsp; Set up on theandnbsp;topmost floor, this has the power to prolong the stay of any occupier who comes to abide in by giving the best view  …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
  • Suitable for children of all ages
  • 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

13 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £400 /night

£2800 - £3800 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casa Romanzaandnbsp;boasts a lovely location on the hilltops of Castelmunzio, a small and delightful village in the undulating Tuscan countryside. andnbsp;Accommodating up toandnbsp;10 persons on two floors, Casa Romanza includes a vast swimming pool and the most  …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
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • 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

20 Photos

Villa | 1 Bedroom | sleeps 10

5 Nights min stay

Add to shortlist

from £343 /night

£2400 - £3200 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Villa Romanzaandnbsp;is a large villa for rent in Tuscany with over 100 years of history.andnbsp;The villa can accommodate up toandnbsp;10 peopleandnbsp;in its lovely duplex apartment situated on theandnbsp;first and second floor of the property.andnbsp;  …see more

13 Photos

Villa | 5 Bedrooms | sleeps 13

7 Nights min stay

Add to shortlist

from £141 /night

£981 - £2083 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 13 persons, with swimming pool , in Cortona  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 16

7 Nights min stay

Add to shortlist

from £677 /night

£4734 - £5118 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Luxury holiday house for 16 persons, with swimming pool , in Chiusi - Chianciano  …see more

20 Photos

Villa | 8 Bedrooms | sleeps 16

1 night min stay

Add to shortlist

from £560 /night

£3920 - £4640 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Ciliegia is a charming three-story historical villa surrounded by a wonderful age-old park. It sleeps 16 people. It is appoximately 600 square meters (6460 square feet). It features a private swimming pool, a private garden and winter heating  …see more

15 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £93 /night

£647 - £878 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This apartment is located in a farm-turned-holiday home built in 1878, in the province of Montepulciano, which is famous for its vineyards. The ancient farm has been totally restored and contains four beautiful apartments. It has its own garden. Today the farm is rec...  …see more

24 Photos

Villa | 8 Bedrooms | sleeps 14

5 Nights min stay

Add to shortlist

from £480 /night

£3360 - £4704 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
A remarkable villa, replete with ancient history, situated in Montepulciano,andnbsp;Villa Dal Pinetto, offers impressive views of vineyards, olive groves, neighbouring towns including Cortona and Chianciano Terme, an ancient town with thermal baths situated around its  …see more