Villas and Holiday homes in Montepulciano

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Montepulciano villas
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40 Villa rentals in Montepulciano

Best Montepulciano villas and holiday homes with a pool

Among the 40 accommodations in Montepulciano, here are the 4 best villas and holiday homes with a pool

Villa Salice Auf Der Locanda Cicolina - Montepulciano
Montepulciano
30/09 – 02/10
SG$985/nighttotal: SG$1970 (2 )

Villa Salice Auf Der Locanda Cicolina

5 3
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.
Le Corolle - Montepulciano
9.1 137 reviews
Montepulciano
25/08 – 29/08
SG$279/nighttotal: SG$1116 (4 )

Le Corolle

2 4
house , Montepulciano
Le Corolle is a holiday home located just 2 kilometres outside of Montepulciano, offering a peaceful retreat close to the town's attractions. The property has consistently received excellent ratings for location, cleanliness and overall user experience.
The self-catering accommodation features a well-equipped kitchenette, a private bathroom, a terrace and a garden. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace, cook up a meal on the barbecue, or make use of the free private parking.
Montepulciano Luxe Escape - Montepulciano
9.4 50 reviews
Montepulciano
05/12 – 08/12
SG$1302/nighttotal: SG$3906 (3 )

Montepulciano Luxe Escape

7 4
house , Montepulciano
This seven-bedroom villa is located in Montepulciano, 21 kilometres from Bagno Vignoni and 27 kilometres from Bagni San Filippo, with Mount Amiata and thermal spas within reach.
This spacious property offers a private swimming pool, hot tub, and Wi-Fi, ideal for families and groups seeking a self-catering retreat with air conditioning and parking.
90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Montepulciano
Montepulciano
19/08 – 21/08
SG$714/nighttotal: SG$1428 (2 )

90 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

2 2
farm , Torrita di Siena
Farm listing for up to 4 people. This accommodation is based in Torrita di Siena.
Services and facilities: a swimming pool, free parking and a dish washer. This accommodation is very convenient for families.

Best Montepulciano villas and holiday homes with a kitchen

60 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Montepulciano
10 6 reviews
Montepulciano
08/08 – 27/08
SG$245/nighttotal: SG$4655 (19 )

60 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

1 2
farm , Montepulciano
Farm rental for up to 2 guests with an excellent rating of 100% based on 6 reviews. You will be based in Montepulciano.
Facilities and services: a terrace, an iron and air conditioning. This accommodation is ideal for families.
Villa Azzurro - Montepulciano
Montepulciano
19/08 – 21/08
SG$487/nighttotal: SG$974 (2 )

Villa Azzurro

1 2
house , Trequanda
This detached house in Trequanda is located 46 kilometres from Piazza Grande and offers convenient access to Bagno Vignoni (24 kilometres) and Bagni San Filippo (38 kilometres).
This 142 square metre villa accommodates up to seven guests with three bedrooms and two bathrooms, featuring air conditioning, a fully equipped kitchen, WiFi, private parking, and an outdoor swimming pool.
110 M² House ∙ 2 Bedrooms ∙ 4 Guests - Montepulciano
Montepulciano
26/06 – 28/06
SG$178/nighttotal: SG$356 (2 )

110 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 4
house , Montepulciano
This villa is located in Acquaviva di Montepulciano, just a few kilometres from the historic town of Montepulciano, offering a tranquil Tuscan countryside setting.
This 110 square metre villa sleeps four guests across two bedrooms and two bathrooms, featuring a private kitchen, air conditioning, a hot tub, and a private terrace with countryside views, with family-friendly amenities and private parking available.
Villa Bravio: A Characteristic And Welcoming Two-story Villa Made Of Stone, With Free Wi-fi. - Montepulciano
Montepulciano
05/12 – 07/12
SG$3111/nighttotal: SG$6222 (2 )

Villa Bravio: A Characteristic And Welcoming Two-story Villa Made Of Stone, With Free Wi-fi.

6 4
house , Montepulciano
This sizeable villa near Montepulciano, Tuscany, is within walking distance of Val di Chiana and a 12-minute walk (approximately 1 km) from the Terme di Montepulciano spa.
The 450-square-metre property boasts six bedrooms, seven bathrooms, sleeps twelve guests, and includes a private pool, garden, parking, and fully equipped kitchen with dishwasher; Wi-Fi is also available.

Frequently asked questions about villa rentals in Montepulciano

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

    Montepulciano is a treasure trove of attractions! The historic centre is a must-see, with the Duomo, Palazzo Comunale, and the Fortezza di Montepulciano being highlights. You can't miss the underground Etruscan tunnels, and the surrounding countryside is dotted with charming villages like Pienza and Cortona, each with its own unique character.
  • 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 countryside around Montepulciano is home to a variety of wildlife. Keep an eye out for red squirrels darting through the trees, hares hopping through the fields, and various bird species like the hoopoe and the golden oriole. If you're lucky, you might even spot a wild boar or a fox in the early morning or late evening.
  • 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?

    Spring (April-May) and autumn (September-October) are the best times to visit, offering pleasant weather and fewer crowds. You'll experience the beauty of the Tuscan countryside in full bloom during spring, and the vibrant colours of autumn foliage in the fall. Summer can be hot and crowded, but the region comes alive with festivals and events.
  • 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?

    Booking a villa rental in the shoulder seasons (April-May and September-October) is often easier and more affordable than during peak season. You'll have a wider selection of properties available and can generally secure better rates. However, if you're looking for a specific villa, it's always best to book well in advance, regardless of the 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?

    Montepulciano is a great base for hiking. The Sentiero del Vino, which follows the old Roman road, offers stunning views of the vineyards and the Val d'Orcia. For a more challenging hike, try the trail to the top of Mount Amiata, the highest peak in the region. And for a leisurely stroll, follow the path along the River Chiana.
  • 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 level of privacy and independence that you won't find in a hotel. You can cook your own meals, relax in your own space, and enjoy the beautiful surroundings at your own pace. It's also a great way to experience the local culture and lifestyle.
  • 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! Montepulciano is perfectly situated for exploring the region. Within a short drive, you can visit the charming hilltop town of Pienza, known for its Renaissance architecture and delicious Pecorino cheese. The historic city of Siena, with its iconic Piazza del Campo, is also within easy reach. And for a taste of the Renaissance, head to Florence, just a couple of hours away.

Destinations nearby

Best Montepulciano villas and holiday homes with a fireplace

Villa Pianoia  Elegance And Historic Charm For Groups And Special Events - Montepulciano
Montepulciano
05/12 – 08/12
SG$4006/nighttotal: SG$12018 (3 )

Villa Pianoia Elegance And Historic Charm For Groups And Special Events

7 4
house , Montepulciano
Villa Pianoia, a large holiday home in the Tuscan countryside between Montepulciano and the Val d'Orcia, offers easy access to attractions such as the Piscine Termali Theia and Terme di Chianciano.
This 450-square-metre, two-level property boasts seven bedrooms, nine bathrooms, and accommodates up to sixteen guests, featuring two living rooms with fireplaces, two dining areas with fully equipped kitchens, a mini pool with a whirlpool, and an Italian garden.
Villa ∙ 7 Bedrooms ∙ 14 Guests - Montepulciano
Montepulciano
05/12 – 08/12
SG$1233/nighttotal: SG$3699 (3 )

Villa ∙ 7 Bedrooms ∙ 14 Guests

7 4
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.
Agriturismo Riposati - Montepulciano
9.7 467 reviews
Montepulciano
19/08 – 21/08
SG$214/nighttotal: SG$428 (2 )

Agriturismo Riposati

2 2
house , Pienza
This house is located near Monticchiello, a charming village just 2 kilometres away, and a short 20-minute drive from the famous town of Montepulciano. It has received excellent ratings for location, cleanliness and user experience.
The house has one bathroom and features a fully equipped kitchen, a garden and free Wi-Fi. Guests can enjoy stunning views of the Val d'Orcia hills and relax in the tranquil garden setting.
House ∙ 3 Bedrooms ∙ 7 Guests - Montepulciano
Montepulciano
01/09 – 06/09
SG$297/nighttotal: SG$1485 (5 )

House ∙ 3 Bedrooms ∙ 7 Guests

3 2
house , Montepulciano
Vacation house to rent for 7 guests. You will be in Montepulciano.
Services and facilities include a swimming pool, a barbecue and free parking. This house in Montepulciano also has a garden!

Best Montepulciano villas and holiday homes with jacuzzi

My Rental Homes - Villa Incanto With Pool Offers An Amazing View Of Montepulicano - Montepulciano
8.8 5 reviews
Montepulciano
05/12 – 08/12
SG$1530/nighttotal: SG$4590 (3 )

My Rental Homes - Villa Incanto With Pool Offers An Amazing View Of Montepulicano

7 4
house , Montepulciano
This seven-bedroom villa is situated in Montepulciano, close to the Torre del Pulcinella and Palazzo Comunale, offering easy access to the natural beauty of Pienza and Val di Chiana.
Sleeping up to 15 guests, this large property boasts a private swimming pool, hot tub, fully equipped kitchen including a dishwasher, and is conveniently located near tourist attractions.
Villa ∙ 6 Bedrooms ∙ 12 Guests - Montepulciano
Montepulciano
01/09 – 06/09
SG$6265/nighttotal: SG$31325 (5 )

Villa ∙ 6 Bedrooms ∙ 12 Guests

6 2
house , Montepulciano
Villa Bene, a luxurious 12-bedroom property, is situated in the countryside between Val di Chiana and Val d'Orcia, 3km from Montepulciano's historic centre and close to Pienza.
This large holiday home boasts a private wellness centre with an indoor heated pool, jacuzzi, and sauna, plus a 1.5km private trail, access to Villa Treci's park, and offers daily breakfast and optional chef-prepared meals.
Tuscan Relais Il Serraglio - Montepulciano
9.8 618 reviews
Montepulciano
25/08 – 29/08
SG$926/nighttotal: SG$3704 (4 )

Tuscan Relais Il Serraglio

2 4
farm , Montepulciano
Il Serraglio is a family-run farm located 3 kilometres from Montepulciano, close to the town's thermal baths and a 15-minute drive from Pienza. The farm has received excellent ratings for its location, cleanliness, and overall experience.
The farm offers a choice of elegantly furnished rooms and apartments. Guests can enjoy amenities including a swimming pool, large gardens, a Jacuzzi, and BBQ facilities.
Cottage In Val D'orcia Tuscany, Jacuzzi & Hot Tub! - Montepulciano
9.9 132 reviews
Montepulciano
19/08 – 21/08
SG$464/nighttotal: SG$928 (2 )

Cottage In Val D'orcia Tuscany, Jacuzzi & Hot Tub!

1 2
house , Chianciano Terme
This charming cottage is situated in the picturesque Val d'Orcia, a UNESCO World Heritage Site, just 15 kilometres from the historic town of Montepulciano. It has received excellent ratings for its location, cleanliness, and overall experience.
The self-catering property offers a private patio with a marble table for al fresco dining, a double Jacuzzi tub, a new memory foam mattress, and a treadmill. Guests can also enjoy the swimming pool, the Swedish hot tub, and the fitness centre, as well as arrange winery tours and tastings.
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