Search Montepulciano villas and holiday homes

62 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Montepulciano villas
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

62 Villa rentals in Montepulciano

Holiday Homes with a Pool in Montepulciano, Italy

Plunge into a cool, private pool after working up a massive sweat on the trails at mountain houses in Montepulciano, Italy.

Corolle2 - Montepulciano
9.6 7 reviews

Corolle2

house, Montepulciano
Corolle2 is a holiday home located in Montepulciano, offering access to Piazza Grande (49 km), Parco dei Mulini (23 km), and Bagni San Filippo (31 km).
This 48 square metre holiday home accommodates up to five guests and features a private swimming pool, a well-equipped kitchen, WiFi, and parking, with pets welcome for an additional charge.
Casa Moscatella: A Characteristic Three-story Age-old Farm House Surrounded By Vineyards And Olive Groves, With Free Wi-fi. - Montepulciano
9.4 50 reviews

Casa Moscatella: A Characteristic Three-story Age-old Farm House Surrounded By Vineyards And Olive Groves, With Free Wi-fi.

house, Montepulciano
This house is located in Montepulciano, just a couple of kilometres from the Val di Chiana and the Church of St. Agnes, offering a peaceful escape from the hustle and bustle of city life. The property has received excellent ratings for location and user experience, with an "OK" rating for cleanliness.
The house is a spacious 250 square metre property with three bedrooms, comfortably accommodating up to six guests. This house offers a private pool, a spa tub, a garden, a terrace, and a fully equipped kitchen, as well as free Wi-Fi and parking.
Poggio Martino - Montepulciano
9.8 377 reviews

Poggio Martino

farm, Cortona
Poggio Martino is a farm stay located in Cignano, Tuscany, just 48 kilometres from Piazza Grande and 24 kilometres from Montepulciano Terme, offering a peaceful escape in the rolling hills. The farm stay has received excellent ratings for location, cleanliness, and overall user experience.
The property features a range of amenities, including a private swimming pool, a well-equipped kitchen, and a terrace with stunning views of the Tuscan countryside. Guests can enjoy relaxing by the pool, preparing their own meals, and exploring the surrounding area, with Cortona just a short drive away.
Villa Salice Auf Der Locanda Cicolina - Montepulciano
10 2 reviews

Villa Salice Auf Der Locanda Cicolina

house, Montepulciano
Villa Salice, a spacious 240 square metre property, is located in Nottola, 48 kilometres from Piazza Grande and 24 kilometres from Bagno Vignoni, offering ample room for up to 19 guests with five bedrooms and four bathrooms. This villa boasts a seasonal swimming pool, a garden, a terrace with pool views, air conditioning, complimentary WiFi, and private parking with an electric vehicle charging station, making it ideal for families and groups seeking a comfortable stay in the Montepulciano region.

Best Montepulciano villas and holiday homes with a kitchen

Casa Il Cipresso - Montepulciano
9.5 2 reviews

Casa Il Cipresso

house, Montepulciano
Casa Il Cipresso, in Sant'Albino near Montepulciano, enjoys a peaceful setting 2.25km from Montepulciano Terme and offers easy access to Mount Amiata, Bagno Vignoni, and Bagni San Filippo.
This 65 square metre house sleeps five, boasting two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, a terrace, garden, free Wi-Fi, parking, and concierge service.
Villa Montepulciano Vineyard - Montepulciano
No reviews

Villa Montepulciano Vineyard

house, Montepulciano
This elegant villa is situated a short walk from Montepulciano's historic centre, offering easy access to the Valdichiana Senese region and its renowned Vino Nobile wine.
This spacious two-level property, covering 300 square metres, accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private swimming pool, Jacuzzi, garden, and modern comforts like air conditioning and underfloor heating, making it an ideal base for exploring Pienza (13 km) and Lake Trasimeno (25 km).
Capanne Di Sopra - Montepulciano
No reviews

Capanne Di Sopra

house, Torrita di Siena
This detached villa in Capanne di Sopra, Montefollonico, is located 14.3 kilometres from Montepulciano Terme and 24.1 kilometres from Bagno Vignoni, with Bagni San Filippo a further 37 kilometres away.
This pet-friendly property accommodates up to 12 guests across 3 bedrooms, offering free WiFi, private parking, a dishwasher, and access to a garden, with a 10:00 AM check-out.
Agriturismo Antica Corte - Montepulciano
9.0 148 reviews

Agriturismo Antica Corte

farm, Montepulciano
Agriturismo Antica Corte is a recently renovated farmhouse situated in the Tuscan countryside, 19km from Montepulciano Terme, 34km from Bagno Vignoni, and 42km from Bagni San Filippo, offering easy access to the thermal baths and Perugia San Francesco d'Assisi Airport (63km away).
This self-catering property features a swimming pool, private gardens, free Wi-Fi, and parking; each unit includes a fully equipped kitchen with a fridge and dishwasher, air conditioning, and one bathroom.

Frequently asked questions about villa rentals in Montepulciano

  • What are the must-see attractions in and around Montepulciano?

    Montepulciano is full of charming sights. You absolutely must visit the Piazza Grande, a stunning square dominated by the Palazzo Comunale. Then, take a walk up to the Fortezza di Montepulciano, offering panoramic views of the surrounding countryside. And don't miss the beautiful Church of San Biagio, a Renaissance masterpiece just outside the city walls.
  • What are the best villa rentals in Montepulciano?

    Among the villa rentals in Montepulciano, Podere Fontecastello, Villa Cicolina and Montorio are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Montepulciano?

    The area around Montepulciano is home to a variety of wildlife. You might spot wild boar, deer, and even the occasional fox in the forests. Keep your eyes peeled for birds of prey like hawks and buzzards soaring overhead. And don't forget to look for the many different types of birds that call the area home.
  • What are the best villa rentals with a pool in Montepulciano?

    Podere Fontecastello, Villa Cicolina and Villa Poggiano are the best villa rentals with a pool in Montepulciano.

  • What is the best time to visit Montepulciano?

    The best time to visit Montepulciano is during the shoulder seasons, from April to May or September to October. The weather is still pleasant, but the crowds are smaller, and you'll find better deals on accommodation. If you're interested in the Bravio delle Botti, a unique wine barrel race, then you'll want to visit in late August.
  • What are the best villa rentals with a jacuzzi in Montepulciano?

    The best villa rentals with a jacuzzi in Montepulciano are Villa Cicolina, Agriturismo Sanguineto and Villa Poliziana San Benedetto.

  • When is it easiest to book a villa rental in Montepulciano?

    The easiest time to book a villa rental in Montepulciano is during the shoulder seasons, or even during the winter months. You'll find more availability and often better prices compared to the peak summer season.
  • What are the best villa rentals for families and kids in Montepulciano?

    The best villa rentals for families and kids in Montepulciano are Podere Fontecastello, Villa Cicolina and Montorio.

  • What are the top hiking trails near Montepulciano?

    There are many great hiking trails around Montepulciano. One popular option is the Sentiero del Vino, a scenic trail that winds through vineyards and olive groves. Another favourite is the trail to the Sanctuary of Madonna di San Biagio, offering stunning views of the surrounding countryside. And for a more challenging hike, try the trail to the top of Mount Amiata.
  • What are the best pet friendly villa rentals in Montepulciano?

    The best pet friendly villa rentals in Montepulciano are Podere Fontecastello, Agriturismo Sanguineto and Villa Poliziana San Benedetto.

  • What are the advantages of renting a house or a villa in Montepulciano

    Renting a villa in Montepulciano offers a lot of advantages. You'll have more space and privacy than in a hotel, and you'll be able to enjoy the freedom of cooking your own meals and relaxing in your own private garden. Plus, many villas have stunning views of the countryside.
  • What are the best villa rentals with parking in Montepulciano?

    Podere Fontecastello, Villa Cicolina and Montorio are the best villa rentals with parking in Montepulciano.

  • Are there popular destinations near Montepulciano?

    Absolutely! Just a short drive from Montepulciano, you'll find the beautiful medieval hill towns of Pienza and Cortona. And if you're looking for a day trip to a larger city, Siena is just an hour away. For a taste of the Tuscan coast, head to the charming seaside town of Castiglione della Pescaia.

Popular destinations

Holiday Homes with a Fireplace in Montepulciano, Italy

Roast marshmallows over a crackling fire while watching the mountain mist roll in at houses with a fireplace in Montepulciano, Italy.

50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Montepulciano
9.4 19 reviews

50 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Montepulciano
Farm for 2 people with an excellent rating of 94% based on 19 reviews. You will be located in Montepulciano.
Facilities and services include event friendly rooms, a washing machine and a spa. This accommodation in Montepulciano has a swimming pool!
Elegant Ground Floor Villa Of 93 M2 Consisting Of A Large Living Room With Sofas And Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Double Bedroom W - Montepulciano
No reviews

Elegant Ground Floor Villa Of 93 M2 Consisting Of A Large Living Room With Sofas And Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer.indoor And Outdoor Dining Area, A Double Bedroom W

house, Trequanda
Cignella Villa Basil, a self-catering villa in Trequanda, Tuscany, is situated within 15km of the Saints Peter and Andrew Church, the Monastery of Sant'Anna in Camprena, Triacca Winery and Enoteca Di Ghino, offering easy access to Val di Chiana's scenic beauty and notable wineries.
This 93 square metre property sleeps four guests in two bedrooms and two bathrooms, boasting a private swimming pool, garden, parking, and in-villa amenities including a fireplace, TV with DVD player, and washing machine.
Typical Big Tuscan Farmhouse, Pool Is Shared - Montepulciano
9.0 31 reviews

Typical Big Tuscan Farmhouse, Pool Is Shared

house, Sarteano
This Tuscan villa near Sarteano, a 15-minute (24km) drive from Montepulciano and an hour (approx. 72km) from Siena, offers a tranquil escape in the beautiful Tuscan countryside.
Sleeping up to twelve guests in five bedrooms and three bathrooms, the property boasts a large private garden, shared swimming pool (open June 1st to early October), a well-equipped kitchen with dishwasher, and the option of pre-booked Tuscan meals; locally produced wines and olive oil are also available on-site.
Il Casale Di Manuele 12, Emma Villas - Montepulciano
10 17 reviews

Il Casale Di Manuele 12, Emma Villas

house, Montepulciano
Il Casale Di Manuele 12, near Montepulciano, is conveniently located 7.7km from Montepulciano Terme, 22.5km from Bagno Vignoni, and 30.6km from Bagni San Filippo, offering easy access to thermal baths and other attractions.
This 250 square metre villa boasts six bedrooms, seven bathrooms, a private pool, and a fully equipped kitchen, ideal for large families or groups seeking a self-catering holiday with ample space and amenities.

Houses with a Hot Tub in Montepulciano, Italy

Soak under a canopy of pine trees in a steaming outdoor hot tub at mountain houses with a hot tub in Montepulciano, Italy.

Podere Le Pozze - Montepulciano
10 2 reviews

Podere Le Pozze

house, Sinalunga
This restored Tuscan farmhouse is located in Sinalunga, offering privacy within its 32 hectares of enclosed land and proximity to landmarks such as Torre Il Cassero and Farneta Abbey.
This 550 square meter rural property sleeps 14 guests across six double bedrooms, featuring a kitchen with a fridge and microwave, air conditioning, a swimming pool, jacuzzi, garden, and on-site parking, with opportunities for exploring the local olive grove and vineyard.
500 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - Montepulciano
No reviews

500 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

house, Cortona
Il Fitto is a secluded villa located on a hillside near Cortona, equidistant from the ancient Etruscan town and Montepulciano, offering panoramic views of the Tuscan landscape and access to a working winery.
This 500 square meter estate accommodates up to 10 guests in 5 bedrooms and features air conditioning, a private swimming pool, jacuzzi, garden, parking, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Beautiful Private Villa With Private Pool, Wifi, Tv, Patio, Pets Allowed And Panoramic View - Montepulciano
9.6 5 reviews

Beautiful Private Villa With Private Pool, Wifi, Tv, Patio, Pets Allowed And Panoramic View

house, Montepulciano
This Montepulciano villa, situated within 1.6km of Val di Chiana and the Church of St Agnes, and under 3.2km from the Colonna del Marzocco and Palazzo Avignonesi, offers easy access to key attractions.
This 250 square metre property boasts three bedrooms, four bathrooms, sleeps six guests, and includes a private pool, Jacuzzi, garden, and fully equipped kitchen with dishwasher; free Wi-Fi is also available.
Villa Licia, Val D'orcia, Private Pool, Jacuzzi, Wifi - Montepulciano
9.4 12 reviews

Villa Licia, Val D'orcia, Private Pool, Jacuzzi, Wifi

house, Chiusi
Villa Recanati, a luxurious property in Val d'Orcia, is located 11.7km from Montepulciano Terme and 50km from Monte Amiata, offering easy access to Chiusi's attractions.
This spacious 500 square metre villa boasts six bedrooms, six bathrooms, and can accommodate up to 27 guests, featuring a private pool, jacuzzi, fitness centre, and extensive outdoor amenities including a barbecue and play areas.

See Guest-Favourite High-End Houses in Montepulciano, Italy

Experience rugged nature with elite five-star comforts and sweeping peak views at luxury mountain houses in Montepulciano, Italy.

Relais Villa Grazianella | Una Esperienze - Montepulciano
9.6 847 reviews

Relais Villa Grazianella | Una Esperienze

farm, Montepulciano

Find the Best Family Holiday Homes in Montepulciano, Italy

Give the kids a classic wilderness adventure with a massive timber home and outdoor space at family mountain houses in Montepulciano, Italy.

Fonte Senesi Villa In Val D'orcia - Montepulciano
9.9 56 reviews

Fonte Senesi Villa In Val D'orcia

gîte, Pienza
Agriturismo La Terra - Montepulciano
9.4 280 reviews

Agriturismo La Terra

farm, Montepulciano
Le Corolle - Montepulciano
9.3 142 reviews

Le Corolle

house, Montepulciano
Villa Lauretana By Posarellivillas - Montepulciano
8.0 2 reviews

Villa Lauretana By Posarellivillas

house, Torrita di Siena
©2026 cozycozy.com