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Montepulciano villas
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40 Villa rentals in Montepulciano

Traveler-Approved Holiday Houses with Swimming Pool in Montepulciano

Take a dip after your hike; these vacation homes in Montepulciano come with a refreshing on-site swimming pool.

House ∙ 1 Bedroom ∙ 3 Guests - Montepulciano
Montepulciano
09/01 – 09/06
$145/nighttotal: $725 (5 )

House ∙ 1 Bedroom ∙ 3 Guests

1 2
house , Montepulciano
Book this vacation rental for up to 3 people. This accommodation is located in Montepulciano.
Facilities and services include a kitchen, a washing machine and a swimming pool. Enjoy free parking with this accommodation in Montepulciano!
Salcheto Winehouse - Montepulciano
9.4 1919 reviews
Montepulciano
09/30 – 10/02
$279/nighttotal: $558 (2 )

Salcheto Winehouse

1 3
farm , Montepulciano
Salcheto Winehouse is located just outside of Montepulciano, a charming town known for its historic architecture and delicious wines. The farm is highly rated, receiving excellent scores for location, cleanliness, and overall user experience.
The farmhouse features a private garden and stylish rooms with modern amenities. Guests can enjoy a sweet buffet breakfast, relax in the heated outdoor hot tub, and explore the on-site wine cellar for tastings and traditional product sampling.
51 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Montepulciano
Montepulciano
08/19 – 08/21
$359/nighttotal: $718 (2 )

51 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

1 2
farm , Torrita di Siena
Farm for 2 guests. You will be located in Torrita di Siena.
Facilities and services include a freeze, rooms suitable for events and free parking. This accommodation is ideal for families.
Tuscan Relais Il Serraglio - Montepulciano
9.8 618 reviews
Montepulciano
08/25 – 08/29
$721/nighttotal: $2884 (4 )

Tuscan Relais Il Serraglio

2 4
farm , Montepulciano
This gîte is located in a rural area of Montepulciano, within 2 miles (3 kilometers) of Val di Chiana, San Biagio, and Terme di Montepulciano Spa, and offers an attached winery, a seasonal outdoor pool, a garden, and barbecue grills.
With excellent user, location, and cleanliness ratings, this gîte features a kitchen with a fridge, freezer, and microwave oven, air conditioning, a swimming pool, a Jacuzzi, a terrace or balcony, a garden, room service, and parking.

Best Montepulciano houses with a kitchen

170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests - Montepulciano
Montepulciano
08/08 – 08/27
$1087/nighttotal: $20653 (19 )

170 M² Villa ∙ 5 Bedrooms ∙ 12 Guests

5 2
house , Montepulciano
Villa Boschetto, a spacious five-bedroom estate in the Val d'Orcia countryside near Montepulciano, offers easy access to the historic town center.
This 1830-square-foot vacation home features five ensuite bathrooms, a fully equipped kitchen with a dishwasher and refrigerator, a private garden with a BBQ and wood-fired oven, and accommodates up to 12 guests.
Villa In Toscana Con Piscina Privata, Relax Natura - Montepulciano
9.7 35 reviews
Montepulciano
12/05 – 12/07
$422/nighttotal: $844 (2 )

Villa In Toscana Con Piscina Privata, Relax Natura

2 4
house , Montepulciano
This luxurious villa is located near Montepulciano, Italy, just 0.6 miles from the historic center and the Temple of San Biagio, offering easy access to Tuscany's renowned attractions.
The two-bedroom, two-bathroom house sleeps four, features a private pool with stunning countryside views, a fully equipped kitchen, air conditioning, and private parking, perfect for a relaxing Tuscan getaway.
Walk To Town-luxury Tuscan Estate-5br+bonus/6.5ba/sleeps 16-infinity Pool & Spa - Montepulciano
10 35 reviews
Montepulciano
07/14 – 07/22
$2878/nighttotal: $23024 (8 )

Walk To Town-luxury Tuscan Estate-5br+bonus/6.5ba/sleeps 16-infinity Pool & Spa

6 2
house , Montepulciano
This Montepulciano villa is conveniently located within a 2 kilometer radius of popular attractions like Val di Chiana, San Biagio, Torre del Pulcinella, Church of St. Agnes, and Cantina Contucci. The property consistently receives excellent ratings from previous guests.
The 5-bedroom home comfortably sleeps up to 14 guests. Enjoy a private pool, a fitness center, a jacuzzi, and a terrace perfect for relaxing and enjoying the Tuscan sunshine.
Villa Poliziana San Benedetto - Montepulciano
9.9 336 reviews
Montepulciano
07/18 – 07/19
$656/nightfor 1 night

Villa Poliziana San Benedetto

2 7
house , Montepulciano
Villa Poliziana San Benedetto is located in the countryside near Montepulciano, about 3 kilometers from the town center and a 12-minute drive from Chianciano Terme.
This 2-bedroom, 2-bathroom villa offers a peaceful escape with a large garden, a swimming pool, a Jacuzzi, and a terrace for outdoor dining, perfect for families or groups of up to 4 guests.

Frequently Asked Questions about villa rentals in Montepulciano

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

    You can't miss the historic center of Montepulciano, with its beautiful Piazza Grande. Take a walk through the underground Etruscan tunnels, and visit the Fortezza, an ancient fortress offering panoramic views of the valley. Just outside of town, you'll find the stunning Chiesa di San Biagio, a Renaissance church with a beautiful facade.
  • 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?

    You'll see plenty of birds, like hawks and owls, in the hills around Montepulciano. If you're lucky, you might spot a fox or a wild boar, but they tend to be shy. The local wildlife is mostly harmless, but it's always a good idea to keep your distance and be respectful of their habitat.
  • 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 in the spring or fall. The weather is perfect for exploring the town and the surrounding countryside, and the crowds are smaller than in the peak summer months. You'll also experience the beauty of the vineyards during harvest season.
  • 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 shoulder seasons, spring and fall, are the best time to book a villa rental in Montepulciano. You'll find better deals and availability, and you'll avoid the crowds and higher prices of the summer months.
  • 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?

    The Sentiero del Vino is a popular hiking trail that takes you through the vineyards and olive groves of the region. For a more challenging hike, try the Sentiero degli Etruschi, which follows an ancient Etruscan road. You can also find shorter trails near the town, like the one leading to the Sanctuary of Madonna di San Biagio.
  • 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 offers privacy, space, and independence. You'll have your own kitchen, so you can prepare your own meals, and you can relax in your private garden or pool without worrying about crowds. It's a great way to experience the local 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?

    Yes, there are many popular destinations near Montepulciano. You can visit the beautiful city of Siena, explore the charming town of Pienza, or take a day trip to the thermal baths of Bagno Vignoni. The region is full of historical sites, beautiful landscapes, and delicious food and wine.

Destinations nearby

Best Montepulciano houses with a fireplace

Agriturismo La Chiusa Tuscany - Montepulciano
Montepulciano
08/19 – 08/21
$6185/nighttotal: $12370 (2 )

Agriturismo La Chiusa Tuscany

18 2
house , Torrita di Siena
La Chiusa is a villa located in the mountains of Torrita di Siena, just a short distance from the Palazzo Borgia and Artemisia Gallery. The surrounding area offers a peaceful escape from the hustle and bustle of city life, allowing you to fully immerse yourself in the tranquility of the Tuscan countryside.
This luxurious estate spans 40,000 square feet and can accommodate up to 40 guests. La Chiusa offers a wide range of amenities, including a swimming pool, spa, and garden, as well as activities like mountain biking, horse riding, and wine tasting.
Casa Cervognano - Montepulciano
9.0 8 reviews
Montepulciano
12/05 – 12/08
$316/nighttotal: $948 (3 )

Casa Cervognano

2 4
house , Montepulciano
Casa Cervognano is a peaceful countryside retreat just 5.8 miles outside of Montepulciano, offering easy access to both the town center and Montepulciano Terme. The villa has received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom villa provides 750 square feet of comfortable living space. Guests can enjoy a private pool and garden, modern amenities like air conditioning and Wi-Fi, and a variety of activities, including barbecue facilities and complimentary bikes for exploring the surrounding area.
Villa In Montepulciano With 7 Bedrooms Sleeps 14 - Montepulciano
Montepulciano
09/01 – 09/06
$1142/nighttotal: $5710 (5 )

Villa In Montepulciano With 7 Bedrooms Sleeps 14

7 2
house , Montepulciano
Villa San Biagio, a large vacation home in the Orcia Valley, is located 1.9 miles from Montepulciano, within walking distance of the town and convenient to Cortona (21 miles) and Montalcino (23 miles).
This seven-bedroom, seven-bathroom estate sleeps fourteen guests and boasts a private pool, Jacuzzi, multiple kitchens, a barbecue with a wood-fired oven, and offers access to guided winery tours and e-bike rentals.
Agriturismo Podere San Pietro - Montepulciano
9.9 134 reviews
Montepulciano
12/05 – 12/08
$229/nighttotal: $687 (3 )

Agriturismo Podere San Pietro

3 4
farm , Montepulciano
Agriturismo Podere San Pietro is located in the Tuscan countryside, just a short drive from Montepulciano, Chianciano Terme, and Pienza. The property boasts excellent ratings for location, cleanliness, and user experience.
The farm offers a comfortable apartment with three bedrooms and one bathroom. Guests can enjoy a fully equipped kitchen, a furnished patio, and access to a fitness center, garden, and parking.

Best Montepulciano villas and beach houses with jacuzzi

Cottage In Val D'orcia Tuscany, Jacuzzi & Hot Tub! - Montepulciano
9.9 132 reviews
Montepulciano
08/19 – 08/21
$361/nighttotal: $722 (2 )

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

1 2
house , Chianciano Terme
This charming cottage is conveniently located in the picturesque Val d'Orcia, a UNESCO World Heritage Site, just a short drive from the enchanting towns of Montepulciano, Pienza, Cortona, and Siena. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The cottage is a one-bedroom, one-bathroom dwelling that comfortably accommodates two guests. It offers a range of amenities, including a private patio, a Swedish hot tub, a fully equipped kitchen, and a luxurious bathroom with a double Jacuzzi tub. Guests can also enjoy the convenience of free Wi-Fi, air conditioning, and access to a shared swimming pool and fitness center.
Podere Santaadele - Montepulciano
8.5 146 reviews
Montepulciano
08/25 – 08/29
$287/nighttotal: $1148 (4 )

Podere Santaadele

2 4
farm , Montepulciano
Podere SantaAdele is a farm stay located 4.3 miles outside of Montepulciano, near the Terme di Montepulciano hot springs, offering a peaceful rural setting. The farm has received very good ratings for location, cleanliness, and overall experience.
The farm offers various accommodations, including rooms and apartments. Guests can enjoy a swimming pool, a garden with barbecue facilities, and free Wi-Fi and parking.
Agriturismo Palazzo Bandino - Wine Cellar, On Reservation Restaurant And Spa - Montepulciano
9.1 445 reviews
Montepulciano
06/26 – 06/28
$242/nighttotal: $484 (2 )

Agriturismo Palazzo Bandino - Wine Cellar, On Reservation Restaurant And Spa

1 4
farm , Chianciano Terme
Agriturismo Palazzo Bandino is located in the countryside near Chianciano Terme, just a short drive from the town center and its famous thermal springs. The farm consistently receives high ratings for its cleanliness, location, and overall experience.
The property offers a variety of accommodations, including rooms with garden views. Guests can enjoy a range of amenities and activities, such as a swimming pool, a spa, a restaurant serving local cuisine, a wine cellar, and a working farm experience.
My Rental Homes - Villa Incanto With Pool Offers An Amazing View Of Montepulicano - Montepulciano
8.8 5 reviews
Montepulciano
12/05 – 12/08
$1190/nighttotal: $3570 (3 )

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

7 4
house , Montepulciano
Villa Incanto, a luxurious Tuscan estate, is located 0.6 miles from Montepulciano, near Chianciano Terme, offering easy access to attractions like the Torre del Pulcinella and Palazzo Comunale.
This seven-bedroom, eight-bathroom villa sleeps fifteen guests and boasts a private pool, Jacuzzi, garden, and access to locally sourced produce, along with amenities including Wi-Fi, air conditioning, and a fully equipped kitchen.
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