Search holiday beach houses in Montepulciano from 100+ sites!

62 available villa offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Montepulciano villas
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

62 Villa rentals in Montepulciano

Best Montepulciano houses with a fireplace

Villa - Podere Monti - Montepulciano
10 2 reviews

Villa - Podere Monti

house, Montepulciano
Villa Podere Monti, located in Sant'Albino, a 12-minute walk from Montepulciano Terme and 30 miles from Mount Amiata, offers easy access to both thermal baths and scenic mountain views.
This recently renovated 5,170-square-foot villa boasts five bedrooms, eight bathrooms, a private pool, jacuzzi, and ample outdoor space perfect for large families or groups, including a playground and barbecue.
Agriturismo I Roseti - Montepulciano
9.7 266 reviews

Agriturismo I Roseti

farm, Montepulciano
Agriturismo I Roseti is located in the Tuscan hills, just a short drive from the thermal baths of Bagno Vignoni and a longer drive from Arezzo, offering a peaceful escape with stunning views of the surrounding countryside. Guests consistently rate the farm highly for its cleanliness, location, and overall experience.
The apartment features a rustic décor and a spacious 540 square feet layout with one bedroom and one bathroom. Enjoy a welcome basket filled with local treats, relax in the garden with BBQ facilities, or prepare your own meals in the kitchenette while staying connected with free Wi-Fi.
Haus Banditello, Blick Auf Das Tal Von Montepulciano - Montepulciano
No reviews

Haus Banditello, Blick Auf Das Tal Von Montepulciano

house, Torrita di Siena
This detached Tuscan villa is situated in the countryside near Montepulciano and Montefollonico, offering panoramic views of the Val d'Orcia and is 0.8 miles from Montefollonico and 4.3 miles from Montepulciano.
This 1400 sq ft villa accommodates up to six guests with three bedrooms, two bathrooms, a fully equipped kitchen, multiple living areas, a furnished courtyard with a barbecue, and access to nearby riding schools, bicycle rentals, and thermal baths.
Villa Salice Auf Der Locanda Cicolina - Montepulciano
10 2 reviews

Villa Salice Auf Der Locanda Cicolina

house, Montepulciano
Villa Salice, a spacious 5-bedroom villa in Nottola, is located 15 miles from Bagno Vignoni and 30 miles from Piazza Grande in Montepulciano.
This air-conditioned residence offers 2580 square feet of living space, accommodates up to 19 guests, and features a kitchen, 4 bathrooms, a swimming pool, a terrace, and free WiFi.

Best Montepulciano villas and beach houses with jacuzzi

Villa Lorena - Montepulciano
8.5 28 reviews

Villa Lorena

farm, Montepulciano
Agriturismo Raggio di Sole, near Montepulciano, Italy, offers a convenient location 3.4 miles from Montepulciano Terme and 30 miles from Mount Amiata.
This family-friendly farmhouse rental boasts a swimming pool, Jacuzzi, and outdoor fireplace, perfect for relaxing and enjoying the stunning Tuscan countryside views; free Wi-Fi and private parking are also provided.
Villa ∙ 7 Bedrooms ∙ 14 Guests - Montepulciano
No reviews

Villa ∙ 7 Bedrooms ∙ 14 Guests

house, Montepulciano
This expansive villa in Montepulciano is located in a quiet district, offering easy access to the town's historic center and the surrounding Tuscan countryside.
This 7-bedroom estate accommodates up to 14 guests with multiple well-equipped kitchens, including one that seats 20, several living areas with fireplaces, air conditioning, WIFI, whirlpool bathtubs, and a washing machine.
Villa Montepulciano By Mmega - Montepulciano
10 1 review

Villa Montepulciano By Mmega

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.
Nobilis Charme Relais - Montepulciano
9.0 12 reviews

Nobilis Charme Relais

gîte, Montepulciano
This gîte is situated in Montepulciano, less than 2 miles from Val di Chiana, the Church of St. Agnes, and Tenuta Valdipiatta.
This farm stay offers air conditioning, a swimming pool, a hot tub, a garden, a sauna, and a rooftop terrace, with a poolside bar and complimentary buffet breakfast available.

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.

Popular destinations

Best Montepulciano houses with a kitchen

Villa Montebella Countryside Retreat In Montepulciano - Montepulciano
9.2 5 reviews

Villa Montebella Countryside Retreat In Montepulciano

house, Montepulciano
Villa Montebella is located in Nottola, a short drive from Montepulciano Terme and Bagno Vignoni, offering easy access to the area's natural hot springs and charming medieval villages. The villa has received excellent ratings for its location, cleanliness, and overall experience.
This 2-bedroom, 2-bathroom house can comfortably accommodate up to 4 guests and offers a peaceful garden setting with stunning mountain views. Enjoy modern amenities like air conditioning, Wi-Fi, and a terrace, perfect for relaxing and enjoying the Tuscan countryside.
Agriturismo Podere Casa Al Vento - Montepulciano
9.7 83 reviews

Agriturismo Podere Casa Al Vento

farm, Montepulciano
Agriturismo Podere Casa al Vento is located just a short 3.1 mile drive from the historic town of Montepulciano, nestled in the peaceful countryside amidst vineyards and olive groves. The farm consistently receives excellent ratings for its location, cleanliness, and overall user experience.
This charming rural retreat offers self-catering accommodations with a traditional Tuscan style. You can enjoy a relaxing stay with amenities like a garden, terrace, free barbecue facilities, and free parking, as well as on-site wine and olive oil tastings.
Villa ∙ 12 Bedrooms ∙ 24 Guests - Montepulciano
10 1 review

Villa ∙ 12 Bedrooms ∙ 24 Guests

house, Montepulciano
Villa Cicolina, a large estate near Montepulciano, Tuscany, offers easy access to the town's historic center and surrounding Tuscan wineries.
This 18th-century villa and its two annexes accommodate up to 24 guests in 12 bedrooms and 11 bathrooms, featuring a 52-foot by 18-foot swimming pool with a hydromassage, a professional kitchen (staff use only), and optional services like breakfast, cooking classes, and wine tastings.
77 M² House ∙ 2 Bedrooms ∙ 5 Guests - Montepulciano
No reviews

77 M² House ∙ 2 Bedrooms ∙ 5 Guests

house, Montepulciano
Vacation house rental for 5 guests. You will be located in Montepulciano.
Services and facilities: a fridge, a barbecue and a garden. Take advantage of the Free Parking with this accommodation 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.

Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Montepulciano
No reviews

Farmhouse ∙ 1 Bedroom ∙ 4 Guests

farm, Chianciano Terme
Farm rental for up to 4 guests. Your accommodation will be based in Chianciano Terme.
Facilities and services: a washing machine, a barbecue and a kitchen. You can bring your favorite pets this accommodation!
Tenuta Santagnese - Montepulciano
9.0 229 reviews

Tenuta Santagnese

farm, Montepulciano
Tenuta Santagnese is a farm located in the Tuscan countryside, just a 10-minute drive from the historic city center of Montepulciano. The farm consistently receives high ratings for its location, cleanliness, and overall experience.
The self-catering apartments feature rustic charm with antique furnishings and spacious kitchens and bathrooms. Guests can enjoy the peaceful setting with access to a swimming pool, barbecue facilities, and a beautiful garden.
Corolle2 - Montepulciano
9.6 8 reviews

Corolle2

house, Montepulciano
Corolle2 is a house located in Montepulciano, 31 miles from Piazza Grande and 15 miles from Bagno Vignoni, with Bagni San Filippo 19 miles away and Perugia San Francesco d'Assisi Airport 45 miles away.
This 520 square foot villa accommodates up to 5 guests, features a fully equipped kitchen, free WiFi, a seasonal outdoor pool with garden views, and a terrace, with pets under 30 kg allowed for a 50 EUR supplement per dog per stay.
La Pievina - Montepulciano
9.7 685 reviews

La Pievina

farm, Montepulciano
La Pievina is a farmhouse located 1.9 miles outside Montepulciano, offering panoramic views of the rolling hills and vineyards of the Val d'Orcia, a UNESCO World Heritage Site. Guests consistently rate the property excellent for its location, cleanliness, and overall experience. This charming country home features a rustic design with wrought iron beds, wooden furniture, and fireplaces in some units. Amenities include a swimming pool, garden, and BBQ area, perfect for relaxing and enjoying the Tuscan countryside.

Guest-Favorite 5-Star Holiday Houses in Montepulciano

A well-chosen luxury vacation home in Montepulciano makes the trip. Discover premium rooms and a location worth the journey.

Casa Evelina - Incredible View, Central Location - Montepulciano
9.6 118 reviews

Casa Evelina - Incredible View, Central Location

apartment, Montepulciano
©2026 cozycozy.com