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Montalcino holiday homes
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25 Villa rentals in Montalcino

Best Montalcino villas and holiday homes with a pool

Among the 25 accommodations in Montalcino, here are the 4 best villas and holiday homes with a pool

Borgo Villa A Tolli - Montalcino
9.4 188 reviews
Montalcino
11/09 – 17/09
NZ$672/nighttotal: NZ$4032 (6 )

Borgo Villa A Tolli

3 4
farm , Montalcino
Borgo Villa a Tolli, a farmhouse in Castelnuovo dell’Abate, offers a peaceful countryside escape near Montalcino, approximately 24km from Bagno Vignoni and 40km from Siena's Piazza del Campo.
This one-bedroom property, boasting 32 square metres of space, sleeps three guests and includes a swimming pool, terrace, garden, and free parking; a delicious Italian breakfast is served daily.
Agriturismo Villa Paradisino Musico - Montalcino
8.9 48 reviews
Montalcino
22/07 – 24/07
NZ$387/nighttotal: NZ$774 (2 )

Agriturismo Villa Paradisino Musico

1 2
farm , Montalcino
Agriturismo Villa Paradisino MUSICO, near Montalcino, is conveniently located 21km from Bagno Vignoni and 42km from Monte Amiata.
This 16-square-metre farmhouse offers one bedroom, four bathrooms, sleeps eight guests, and boasts a swimming pool, bar, and private parking, plus free Wi-Fi.
Villa Brunello - Twelve Bedroom Villa, Sleeps 24 - Montalcino
Montalcino
14/08 – 16/08
NZ$12229/nighttotal: NZ$24458 (2 )

Villa Brunello - Twelve Bedroom Villa, Sleeps 24

12 3
house , Montalcino
This expansive villa in Montalcino offers a prime Tuscan location, situated 2.1 kilometres from Montalcino Fortress and 5.9 kilometres from Amiata Mountain Park, with convenient access to renowned wineries and gardens such as Leonini Gardens.
This property boasts 550 square meters of floor area, accommodating up to 24 guests with 12 bedrooms and 1 bathroom, and features private parking, air conditioning, a swimming pool, and complimentary Wi-Fi for a comfortable stay.
Mastrojanni Relais - Montalcino
9.7 613 reviews
Montalcino
14/08 – 16/08
NZ$2733/nighttotal: NZ$5466 (2 )

Mastrojanni Relais

2 3
farm , Montalcino
Mastrojanni Relais is a farm stay located in Castelnuovo dell’Abate, just 39 kilometres from both Siena and Saturnia, offering a peaceful rural setting near popular tourist destinations. The property has received excellent ratings for location, cleanliness and user experience.
The accommodation features private bathrooms, flat-screen TVs and free Wi-Fi in each room, along with a range of amenities such as a swimming pool, a sauna, a spa, a restaurant, a bar and a fitness centre. Guests can also enjoy a terrace, a garden and room service.

Best Montalcino villas and holiday homes with a kitchen

Casa Vacanze Elisabetta - Montalcino
9.4 54 reviews
Montalcino
14/08 – 16/08
NZ$339/nighttotal: NZ$678 (2 )

Casa Vacanze Elisabetta

2 3
house , Montalcino
CASA VACANZE ELISABETTA is located in Montalcino, just 40 kilometres from Mount Amiata and 42 kilometres from Piazza del Campo in Siena, offering a peaceful setting with views of the surrounding countryside. The property has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom house can accommodate up to four guests and features a fully equipped kitchen with a fridge and dishwasher, a comfortable seating area, and a modern bathroom with a bidet, shower, and hairdryer. Guests can enjoy free private parking, scenic views from the garden, and easy access to nearby attractions like Bagno Vignoni and Bagni San Filippo.
Casa Vacanze Porta Vecchia - Montalcino
9.6 146 reviews
Montalcino
14/08 – 16/08
NZ$290/nighttotal: NZ$580 (2 )

Casa Vacanze Porta Vecchia

1 3
house , Montalcino
Casa Vacanze Porta Vecchia is situated in Sant’Angelo in Colle, just 9km from the centre of Montalcino and 22km from San Quirico D’orcia, offering a peaceful countryside setting within easy reach of the region's attractions. This property has received excellent user ratings for its location, cleanliness, and overall experience.
The holiday home comprises a single bedroom and bathroom, totalling 45 square metres. Guests can enjoy a range of amenities including a garden with BBQ facilities, a terrace, air conditioning, free Wi-Fi, and parking.
Azienda Agraria La Casella - Montalcino
8.9 615 reviews
Montalcino
27/06 – 28/06
NZ$394/nightfor 1 night

Azienda Agraria La Casella

1 2
farm , Montalcino
Azienda Agraria La Casella is a farm stay located just outside the centre of Montalcino, a 5-minute walk from the town and 40 kilometres from Siena, offering a peaceful rural setting close to the town's attractions. The property has excellent ratings for location, cleanliness and overall experience.
The accommodation features a traditional Tuscan style with a bedroom, bathroom, kitchen and a terrace or balcony. Guests can enjoy a communal breakfast in the dining room or a breakfast basket delivered to their room, relax in the garden, use the barbecue facilities, and dine at the farm's restaurant serving traditional Tuscan cuisine.
Casa Al Colle Buonconvento - Montalcino
9.1 20 reviews
Montalcino
14/08 – 16/08
NZ$621/nighttotal: NZ$1242 (2 )

Casa Al Colle Buonconvento

3 3
house , Buonconvento
Casa Al Colle Buonconvento, situated in Buonconvento, Tuscany, is conveniently located approximately 29 kilometres from Siena’s Piazza del Campo and offers easy access to attractions such as Palazzo Chigi-Saracini and the National Picture Gallery.
This 130 square metre property sleeps up to 16 guests, boasting three bedrooms, two bathrooms, free Wi-Fi, private parking, and a well-equipped kitchen including a fridge and microwave; nearby cycling and hiking trails are perfect for exploring the Tuscan countryside.

Frequently asked questions about villa rentals in Montalcino

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

    You absolutely must visit the Fortezza di Montalcino, a 14th-century fortress offering stunning views of the surrounding countryside. Don't miss the Museo del Vino, showcasing the history of Brunello di Montalcino wine. And for a day trip, head to the nearby Abbey of Sant'Antimo, a stunning example of Romanesque architecture.
  • What are the best villa rentals in Montalcino?

    Among the villa rentals in Montalcino, Charming House In Montalcino With City View, Montalcino - Casa Gelsomino - Con Giardino and Agriturismo Collodi are the most popular ones.

  • What types of wildlife can travelers expect to see in the area of Montalcino?

    The area around Montalcino is home to a variety of wildlife. You might spot wild boar, deer, and foxes in the forests. Keep an eye out for birds of prey like buzzards and kestrels soaring overhead. If you're lucky, you might even see a rare golden eagle.
  • What are the best villa rentals with a pool in Montalcino?

  • What is the best time to visit Montalcino?

    The best time to visit Montalcino is during the shoulder seasons, from April to May or September to October. The weather is pleasant, the crowds are smaller, and you'll enjoy a more relaxed atmosphere. If you're a wine enthusiast, you can also visit during the harvest season in September and October.
  • What are the best villa rentals with a jacuzzi in Montalcino?

  • When is it easiest to book a villa rental in Montalcino?

    The easiest time to book a villa rental is during the off-season, from November to March. You'll have more options and often find better prices. However, if you're planning a trip during the peak season, it's best to book well in advance, especially if you have specific preferences.
  • What are the best villa rentals for families and kids in Montalcino?

    The best villa rentals for families and kids in Montalcino are Charming House In Montalcino With City View, Montalcino - Casa Gelsomino - Con Giardino and Agriturismo Collodi.

  • What are the top hiking trails near Montalcino?

    One of the most popular trails is the Sentiero del Brunello, a 10km circular route that takes you through vineyards and olive groves, offering breathtaking views of the Val d'Orcia. For a more challenging hike, try the Sentiero del Lupo, a 15km trail that leads you to the top of Mount Amiata, the highest peak in the region.
  • What are the best pet friendly villa rentals in Montalcino?

  • What are the advantages of renting a house or a villa in Montalcino

    Renting a villa in Montalcino offers the privacy and flexibility of a home away from home. You can enjoy your own space, cook your own meals, and explore the area at your own pace. It's also a great option for families or groups of friends who want to travel together.
  • What are the best villa rentals with parking in Montalcino?

  • Are there popular destinations near Montalcino?

    Yes, there are plenty of popular destinations within easy reach of Montalcino. Just a short drive away, you can visit Siena, a beautiful medieval city with a stunning Piazza del Campo. Or head south to Pienza, a charming town known for its Renaissance architecture and delicious Pecorino cheese.

Destinations nearby

Best Montalcino villas and holiday homes with a fireplace

Colle Al Matrichese - Historic Winery - Montalcino
9.1 107 reviews
Montalcino
10/07 – 12/07
NZ$402/nighttotal: NZ$804 (2 )

Colle Al Matrichese - Historic Winery

1 2
house , Montalcino
This Montalcino holiday home, near Colle al Matrichese, is situated 40km from Piazza del Campo in Siena and 42km from Monte Amiata.
The property boasts a fully equipped kitchen, terrace, garden, private parking, Wi-Fi, and on-site massage services, offering guests a tranquil retreat in the renowned Montalcino wine region with bicycle rental available for exploring the Tuscan countryside.
150 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Montalcino
Montalcino
11/09 – 17/09
NZ$2146/nighttotal: NZ$12876 (6 )

150 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

3 4
house , Montalcino
This Montalcino villa is situated in Piazza della Fortezza, offering immediate access to shops and the 14th-century fortress, with Abbazia di Sant'Antimo 10km, Bagno Vignoni 18km, Pienza 23km, Montepulciano 39km, Siena 45km, Orvieto 100km, Florence 110km, and Rome 200km away.
The 150 square metre property features three en-suite bedrooms sleeping six, a fully equipped kitchen, a private Jacuzzi, a furnished terrace with panoramic views, free Wi-Fi, and complimentary use of electric bicycles, plus private parking – a rare find in Montalcino.
Agriturismo Villa Paradisino Musico - Montalcino
Montalcino
01/08 – 08/08
NZ$378/nighttotal: NZ$2646 (7 )

Agriturismo Villa Paradisino Musico

1 2
farm , Montalcino
Agriturismo Villa Paradisino Musico is situated on the slopes of Montalcino, Tuscany, just 0.6km from the historic town centre, offering easy access to shops and restaurants.
This one-bedroom guesthouse provides accommodation for two guests, featuring air conditioning, a terrace, and a garden, alongside organic wine tasting and guided tours of the vineyard and olive grove.
Agriturismo L'arte Dei Semplici - Montalcino
8.8 474 reviews
Montalcino
11/09 – 17/09
NZ$725/nighttotal: NZ$4350 (6 )

Agriturismo L'arte Dei Semplici

4 4
farm , Montalcino
Agriturismo l'arte dei semplici, a farm stay near Montalcino, is located in the Tuscan countryside, 37 kilometres from Mount Amiata and 45 kilometres from Siena's Piazza del Campo.
The property features a swimming pool with panoramic views, a restaurant serving traditional Tuscan cuisine, a garden with outdoor play equipment, and a dedicated picnic area.

Best Montalcino villas and holiday homes with jacuzzi

Borgo Canalicchio Di Sopra Relais - Montalcino
9.5 251 reviews
Montalcino
22/07 – 24/07
NZ$615/nighttotal: NZ$1230 (2 )

Borgo Canalicchio Di Sopra Relais

1 2
farm , Montalcino
Borgo Canalicchio Di Sopra Relais is located in the Val d'Orcia Valley, just 1.6 kilometres from the historic town of Montalcino. The farm has received excellent ratings for location, cleanliness and overall user experience.
The property offers spacious apartments with full kitchens, comfortable lounge areas, and air conditioning. Guests can enjoy the two outdoor pools, the spa, the garden, and the on-site restaurant serving authentic Tuscan cuisine.
Tenuta Bosco Di Pietra - Montalcino
Montalcino
11/09 – 17/09
NZ$6431/nighttotal: NZ$38586 (6 )

Tenuta Bosco Di Pietra

1 4
gîte , Montalcino
Tenuta Bosco di Pietra is a luxuriously restored farmhouse offering panoramic views of Montalcino and the Val d'Orcia hills, located in the Tuscan countryside surrounded by vineyards, approximately 3 kilometers from Montalcino.
This family-friendly gîte accommodates up to 10 guests across 5 bedrooms and 5 bathrooms, featuring air conditioning, Wi-Fi, a gourmet kitchen with Gaggenau and Miele appliances, a living area with a fireplace, and an expansive terrace with a Jacuzzi and dining facilities, all set within a landscaped park.
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