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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.

Villa Montepulciano By Mmega - Montepulciano
10 1 review
Montepulciano
06/20 – 06/27
$1064/nighttotal: $7448 (7 )

Villa Montepulciano By Mmega

7 2
house , Montepulciano
This luxurious Montepulciano villa, boasting 5,380 square feet, is ideally situated within two miles of Val di Chiana, the Terme di Montepulciano Spa, and the Church of St. Agnes, with easy access to San Biagio and the Colonna del Marzocco.
This seven-bedroom, eight-bathroom residence comfortably sleeps sixteen guests and features a private pool with Tuscan countryside views, a hot tub, a fully equipped kitchen, laundry facilities, barbecue grills, and a fireplace; it also offers Wi-Fi access and is pet-friendly.
Agriturismo Sanguineto - Montepulciano
8.7 915 reviews
Montepulciano
06/30 – 07/01
$209/nightfor 1 night

Agriturismo Sanguineto

1 4
house , Montepulciano
Agriturismo Sanguineto is located in the Tuscan countryside, just a short drive from Montepulciano, Pienza, Cortona, and Siena, offering a peaceful escape surrounded by vineyards and olive groves. This accommodation receives very good ratings for cleanliness, user experience, and location.
The renovated farmhouse combines traditional charm with modern amenities, including a swimming pool. Guests can enjoy a spa area with a sauna, Turkish bath, and spa showers, as well as wine and food tasting tours, and a fitness center.
Cottage Elena-podere Poggioalsole - Montepulciano
9.8 119 reviews
Montepulciano
08/22 – 08/29
$460/nighttotal: $3220 (7 )

Cottage Elena-podere Poggioalsole

2 4
house , Montepulciano
Podere Poggio al sole is a charming villa located just a short distance from the charming town of Montepulciano, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
This vacation rental features a private terrace, a garden, and an infinity pool with views of the surrounding countryside. Enjoy amenities like air conditioning, a fully equipped kitchen, and free parking, along with activities like hiking, exploring the town, and relaxing by the pool.
La Pievaccia - Montepulciano
9.1 25 reviews
Montepulciano
08/01 – 08/08
$128/nighttotal: $896 (7 )

La Pievaccia

2 3
house , Castiglione del Lago
This country house, La Pievaccia in Binami, is located near Castiglione del Lago, 41 miles from Perugia San Francesco d'Assisi Airport, and approximately 25 miles from Bagno Vignoni and 26 miles from Bagni San Filippo.
This pet-friendly, family-friendly villa features a swimming pool with a view, a garden with barbecue facilities, a sun terrace, an outdoor fireplace, and fully equipped kitchens, offering a great option for travelers seeking a countryside escape with ample amenities.

Best Montepulciano houses with a kitchen

House ∙ 3 Bedrooms ∙ 7 Guests - Montepulciano
Montepulciano
09/04 – 09/11
$225/nighttotal: $1575 (7 )

House ∙ 3 Bedrooms ∙ 7 Guests

3 2
house , Montepulciano
House to rent for up to 7 people. This accommodation is based in Montepulciano.
Services and facilities: free parking, a garden and a barbecue. This is a pet-friendly house!
Villa ∙ 6 Bedrooms ∙ 12 Guests - Montepulciano
Montepulciano
08/09 – 08/15
$4863/nighttotal: $29178 (6 )

Villa ∙ 6 Bedrooms ∙ 12 Guests

6 4
house , Montepulciano
Villa Bene, a luxurious 12-bedroom estate, is situated between the Val di Chiana and Val d'Orcia valleys, approximately 1.9 miles from Montepulciano's historic center and near Pienza.
This large vacation rental boasts a private wellness center with an indoor heated pool, Jacuzzi, sauna, and spa, plus a 1-mile walking trail, access to the adjacent Villa Treci park, and complimentary daily breakfast.
Le Colombelline 12, Emma Villas - Montepulciano
9.5 2 reviews
Montepulciano
07/25 – 07/30
$2538/nighttotal: $12690 (5 )

Le Colombelline 12, Emma Villas

6 2
house , Montepulciano
LE COLOMBELLINE 12, near Montepulciano, Italy, is conveniently located 3.5 miles from Montepulciano Terme, 13 miles from Bagno Vignoni, and 17 miles from Bagni San Filippo.
This 3440-square-foot villa boasts six bedrooms, seven bathrooms, and accommodates up to 23 guests, featuring a private pool, fully equipped kitchen, free Wi-Fi, and parking.
Villa Pianoia  Elegance And Historic Charm For Groups And Special Events - Montepulciano
Montepulciano
07/13 – 07/16
$3091/nighttotal: $9273 (3 )

Villa Pianoia Elegance And Historic Charm For Groups And Special Events

7 3
house , Montepulciano
Villa Pianoia, a luxurious Tuscan estate between Montepulciano and the Val d'Orcia, offers easy access to the historic center of Montepulciano and other nearby attractions.
This 4,844-square-foot, two-story villa boasts seven bedrooms, eight bathrooms, and accommodates up to sixteen guests, featuring a Jacuzzi, a mini-pool with a whirlpool, and multiple living areas with fully equipped kitchens.

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

'La Casa' Luxury Townhome - Borgo Di Sotto Tuscany - Montepulciano
9.6 5 reviews
Montepulciano
10/02 – 10/04
$596/nighttotal: $1192 (2 )

'La Casa' Luxury Townhome - Borgo Di Sotto Tuscany

1 5
house , Torrita di Siena
This three-story townhouse, located in Montefollonico—a hilltop village a 15-minute drive from Montepulciano and Pienza—offers easy access to Tuscany's renowned wine region.
The 6-guest property features two bathrooms, a private suite with a fireplace and rain shower, plus a spacious living room, artisanal kitchen, and two bedrooms with air conditioning, all showcasing eco-conscious design elements; free parking is available nearby.
Agriturismo Podere San Gregorio - Montepulciano
9.3 470 reviews
Montepulciano
08/01 – 08/08
$238/nighttotal: $1666 (7 )

Agriturismo Podere San Gregorio

1 3
farm , Pienza
Agriturismo Podere San Gregorio is a charming farmhouse located just outside Pienza, a short walk from the town center and a short drive from Montepulciano and Siena. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This farmhouse features one bedroom with wood-beamed ceilings and terracotta floors. Guests can enjoy a peaceful garden with BBQ facilities, a complimentary breakfast basket, free Wi-Fi, and free parking.
La Burraia Di Anna - Montepulciano
Montepulciano
08/01 – 08/08
$527/nighttotal: $3689 (7 )

La Burraia Di Anna

4 3
house , Montepulciano
La Burraia di Anna is a vacation home located in the Abbadia di Montepulciano district, 25 miles from Bagni San Filippo, 30 miles from Piazza Grande, and 20 miles from Bagno Vignoni.
This 2100 sq ft air-conditioned villa accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, WiFi, a private garden with barbecue, a seasonal outdoor pool, and private parking.
Apartment In A Hotel "Villa Pesca" With Shared Pool, Private Balcony & Wi-fi - Montepulciano
Montepulciano
06/30 – 07/01
$1429/nightfor 1 night

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

3 4
house , Trequanda
This house is located in Trequanda, putting you within a 10-mile drive of Pienza and Montepulciano, and approximately 30 miles from Siena and Florence.
This 1680 sq ft residence offers 3 bedrooms and 3 bathrooms accommodating up to 6 guests, with amenities including Wi-Fi, air conditioning, a dishwasher, a private balcony, and access to a shared swimming pool, with optional services like breakfast and cooking classes available.

Best Montepulciano villas and beach houses with jacuzzi

Montepulciano Central Villa – Sauna & Jacuzzi - Montepulciano
9.7 145 reviews
Montepulciano
10/02 – 10/04
$806/nighttotal: $1612 (2 )

Montepulciano Central Villa – Sauna & Jacuzzi

1 5
house , Montepulciano
This charming home is in the heart of Montepulciano, just steps away from Piazza Grande, one of the town's most beautiful squares. It has consistently received excellent ratings for cleanliness, location, and overall experience.
This spacious vacation rental spans three levels and comfortably accommodates up to 10 guests. Enjoy a jacuzzi, sauna, fireplace, and fully equipped kitchen, along with stunning views of the Tuscan countryside.
Private Villa With Private Pool, Sauna, Wifi, Hot Tub, A/c, Tv, Veranda, Close To Montepulciano - Montepulciano
Montepulciano
08/22 – 08/29
$4567/nighttotal: $31969 (7 )

Private Villa With Private Pool, Sauna, Wifi, Hot Tub, A/c, Tv, Veranda, Close To Montepulciano

6 4
house , Montepulciano
This luxurious 6-bedroom villa, near Montepulciano, Italy, is located within 1.2 miles of the Val di Chiana and Triacca Winery, and under 3 miles from San Biagio and Torre del Pulcinella, offering easy access to Tuscan wine regions and historical sites.
This 4310-square-foot estate boasts a private pool with stunning countryside views, a fully equipped kitchen, 6 bathrooms, a sauna, a hot tub, and accommodates up to 12 guests, perfect for large families or groups seeking a relaxing Tuscan getaway.
Tuscan Oasis Overlooking Montepulciano, Villa With Pool And Exclusive Garden - Montepulciano
Montepulciano
08/22 – 08/29
$434/nighttotal: $3038 (7 )

Tuscan Oasis Overlooking Montepulciano, Villa With Pool And Exclusive Garden

3 4
house , Montepulciano
This Montepulciano villa is located a 5-minute walk from Val di Chiana, 11 minutes by car from Terme di Montepulciano Spa, 4 minutes by car from Palazzo Avignonesi, and 6 minutes by car from San Biagio.
This 3-bedroom, 3-bathroom vacation rental accommodates up to 6 guests and features a private pool, jacuzzi, terrace, garden, and onsite parking with free WiFi.
Villa Montepulciano Vineyard - Montepulciano
Montepulciano
07/25 – 07/28
$678/nighttotal: $2034 (3 )

Villa Montepulciano Vineyard

4 3
house , Montepulciano
This elegant villa is located in Montepulciano, Tuscany, a short walk from the historic center and its underground cellars, within the Valdichiana Senese region.
This 3,230 sq ft home accommodates 10 guests across 4 bedrooms and 3 bathrooms, featuring a private pool, Jacuzzi, air conditioning, Wi-Fi, and an outdoor dining area, serving as an ideal base for exploring southern Tuscany and Umbria, with Pienza 7.9 miles away.
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