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Montepulciano villas
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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.

Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi - Montepulciano
No reviews

Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi

house, Trequanda
This detached villa is located in Trequanda, a Tuscan town with convenient access to Siena (60 kilometres), Florence (100 kilometres), Pienza (20 kilometres), and Montepulciano (15 kilometres).
This 156 square meter, two-storey holiday home offers three bedrooms, three bathrooms, and accommodates up to six guests, featuring Wi-Fi, air conditioning, a dishwasher, a private balcony, and access to a shared swimming pool.
300 M² Villa ∙ 6 Bedrooms ∙ 12 Guests - Montepulciano
No reviews

300 M² Villa ∙ 6 Bedrooms ∙ 12 Guests

house, Montepulciano
This Tuscan farmhouse, situated 3km from Montepulciano's historic centre and 5km from an underground cellar offering Vino Nobile di Montepulciano tastings, boasts stunning panoramic views of the surrounding countryside.
The 300-square-metre property comprises a restored 16th-century tower and modern annex, sleeping up to twelve guests in six bedrooms and six bathrooms, and includes a private swimming pool, garden, parking, and all amenities.
Typical Tuscan Villa Between Wineyards And Olive Trees - Montepulciano
10 1 review

Typical Tuscan Villa Between Wineyards And Olive Trees

house, Sarteano
This five-bedroom villa near Sarteano, in the Val di Chiana, is less than 5km from the Sarteano Archaeological Museum and Castle, and within 10km of Chianciano Terme's art museum and thermal baths.
The 170 square metre property boasts three bathrooms, a private pool, garden, and parking, comfortably sleeping 12 guests and offering a fully equipped kitchen, laundry facilities, and optional housekeeping.
Salcheto Winehouse - Montepulciano
9.4 1944 reviews

Salcheto Winehouse

farm, Montepulciano
Salcheto Winehouse is a vineyard farm located just a short 3.7-mile drive from the historic town of Montepulciano, offering a peaceful escape surrounded by rolling Tuscan hills. The property consistently receives excellent ratings for its location, cleanliness, and overall experience.
The farm offers a range of accommodation options, from stylish rooms to spacious apartments, all featuring modern amenities and private outdoor spaces. Guests can enjoy a variety of activities on-site, including wine tastings, exploring the traditional wine cellar, and relaxing in the heated outdoor hot tub.

Best Montepulciano villas and holiday homes with a kitchen

500 M² Villa ∙ 7 Bedrooms ∙ 16 Guests - Montepulciano
No reviews

500 M² Villa ∙ 7 Bedrooms ∙ 16 Guests

house, Montepulciano
Villa Montepulciano, in the Val d'Orcia, is located 1 kilometre from Montepulciano, offering easy walking access to this historic Tuscan town.
This 500 square metre property sleeps up to 16 guests in 7 bedrooms and 7 bathrooms, boasting a private pool, spa, extensive gardens, and parking for 8 cars.
Il Melograno - Montepulciano
9.2 25 reviews

Il Melograno

house, Torrita di Siena
Il Melograno is a charming apartment located in Torrita di Siena, a town in the Tuscan countryside, just 53 km from Siena and 43 km from Arezzo. The apartment has received very good user, location and excellent cleanliness ratings.
This two-bedroom apartment has one bathroom and offers a terrace with garden views. Guests can enjoy the convenience of a fully equipped kitchen, free parking, and a garden, making it a great choice for families or groups looking for a relaxing and comfortable stay.
Casale Dei 12, Emma Villas - Montepulciano
No reviews

Casale Dei 12, Emma Villas

house, Montepulciano
Casale Dei 12 is situated in the Tuscan countryside, just 10.6 kilometres from Montepulciano Terme and 25.7 kilometres from Bagno Vignoni. This charming property is set in a peaceful location, perfect for those seeking a relaxing getaway.
This spacious villa offers six bedrooms and six bathrooms, covering a generous 300 square metres. Enjoy a private pool, a hot tub, a spa, and a beautiful garden, perfect for enjoying the Tuscan sunshine and indulging in some relaxation.
Sangiovese 14, Emma Villas - Montepulciano
No reviews

Sangiovese 14, Emma Villas

house, Montepulciano
This restored stone farmhouse, Sangiovese, is located in the Val di Chiana, a short drive from Montepulciano, amid Tuscan vineyards producing Nobile di Montepulciano wine, and offers proximity to Pienza and Cortona.
This 350 sq m country house, divided into two independent units, accommodates up to 14 guests with 5 bathrooms, air conditioning, a 3,500 sq m park featuring a swimming pool and barbecue area, and opportunities for on-site wine tastings.

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.

Residenza Al Poggio Degli Ulivi - Montepulciano
9.5 72 reviews

Residenza Al Poggio Degli Ulivi

house, Montepulciano
Residenza al Poggio degli Ulivi is situated just outside Montepulciano's historic centre, offering a peaceful setting with stunning views of the surrounding countryside and nearby lake, just 48km from Perugia San Francesco d'Assisi Airport and 48km from Mount Amiata. This charming property has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The house offers 85 square metres of living space, comfortably accommodating up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private terrace, a barbecue, outdoor play equipment, a fully equipped kitchen, air conditioning, free Wi-Fi, and private parking.
Montepulciano Lovely Apartment In Tuscany Farmhouse With Swimming Pool, Wifi. - Montepulciano
No reviews

Montepulciano Lovely Apartment In Tuscany Farmhouse With Swimming Pool, Wifi.

farm, Montepulciano
This farm stay, offering 60 square metres of accommodation, is situated in the rural outskirts of Montepulciano, providing proximity to local landmarks like Colonna del Marzocco and Palazzo Avignonesi.
This property sleeps up to 4 guests across two bedrooms and features a kitchen with a fridge, microwave oven, and dishwasher, alongside a garden and swimming pool with panoramic views of Montepulciano.
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.
Agriturismo Il Pornelleto - Villa Alari - Montepulciano
8.8 110 reviews

Agriturismo Il Pornelleto - Villa Alari

farm, Cetona
Agriturismo Villa Alari, a renovated farmhouse stay near Cetona in Tuscany, is situated 19 kilometres from Montepulciano Terme and 35 kilometres from Bagno Vignoni.
This property boasts a swimming pool, hot tub, and spa, alongside a restaurant, bar, and fitness centre, offering a range of amenities and activities for guests.

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.

Villa ∙ 7 Bedrooms ∙ 14 Guests - Montepulciano
No reviews

Villa ∙ 7 Bedrooms ∙ 14 Guests

house, Montepulciano
This expansive villa is located in a district of Montepulciano providing easy access to the town's historic centre, a UNESCO World Heritage site renowned for its Renaissance architecture.
Offering accommodation for up to 14 guests, this property features seven bedrooms, multiple well-equipped kitchens including one with seating for 20, a swimming pool, Jacuzzi, air conditioning, and WIFI throughout, with six bedrooms boasting ensuite bathrooms and several with whirlpool bathtubs.
400 M² Villa ∙ 6 Bedrooms ∙ 18 Guests - Montepulciano
No reviews

400 M² Villa ∙ 6 Bedrooms ∙ 18 Guests

house, Chiusi
This luxurious Tuscan villa, near Chiusi, is situated in the countryside between Tuscany and Umbria, a short drive (approximately 30km) from Montepulciano and Pienza, offering easy access to Perugia, Assisi, and Siena.
This 400 square metre property boasts six bedrooms sleeping up to eighteen guests, a heated swimming pool, jacuzzi, sauna, spa, restaurant, and daily butler and chef service, including continental breakfast and at least one other meal (with optional three-meal service).
La Casa Di Emanuela - Montepulciano
9.5 9 reviews

La Casa Di Emanuela

house, Montepulciano
La Casa di Emanuela, a two-bedroom villa in Nottola, is conveniently located 9.2km from Montepulciano Terme, 24km from Bagno Vignoni, and 32km from Bagni San Filippo.
This 70 square metre property sleeps seven, boasting a private pool with Tuscan countryside views, a fully equipped kitchen, two bathrooms (one with a hot tub), a garden, and free Wi-Fi and parking; nearby activities include exploring the thermal baths.
Villa Pianoia | Panoramic Tuscan Private Estate - Montepulciano
10 16 reviews

Villa Pianoia | Panoramic Tuscan Private Estate

house, Montepulciano
Villa Pianoia, a large holiday home near Montepulciano, enjoys a hilltop position overlooking the medieval town and the Val d'Orcia, offering stunning views.
This 450 square metre, two-level property sleeps up to 16 guests in seven en-suite bedrooms, and boasts two kitchens, multiple living areas, a private mini-pool with hydromassage, and a large garden with dining areas; optional chef service is available.

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.

200 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - Montepulciano
No reviews

200 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

house, 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.

Il Grillo 10, Emma Villas - Montepulciano
No reviews

Il Grillo 10, Emma Villas

house, Montepulciano
Villa Salice Auf Der Locanda Cicolina - Montepulciano
10 2 reviews

Villa Salice Auf Der Locanda Cicolina

house, Montepulciano
170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests - Montepulciano
No reviews

170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests

house, Montepulciano
La Burraia 18, Emma Villas - Montepulciano
No reviews

La Burraia 18, Emma Villas

house, Montepulciano