This charming house is located in the heart of Montalcino, just a short walk from the town square and the fortress. It has received excellent ratings for location, cleanliness, and overall experience. The house has three bedrooms and three bathrooms, comfortably accommodating up to six guests. It offers a fully equipped kitchen, a private jacuzzi, a barbecue, and a beautiful terrace with stunning views of the Val d'Orcia.
9.1 237 reviews
Montalcino
08/07 – 08/17
$193/nighttotal: $1930 (10 )
Agriturismo Grossola
1 3
farm , Castiglione d'Orcia
Agriturismo Grossola, a certified organic farm, is located a short 10-minute drive from Castiglione d'Orcia, Tuscany, near Mount Amiata (approximately 6.2 miles) and about an hour from Siena. This one-bedroom, one-bathroom rental offers 220 square feet of space, a swimming pool (open May-September), on-site parking, Wi-Fi, and a restaurant serving breakfast with homemade treats; yoga classes are offered in July.
9.1 168 reviews
Montalcino
08/06 – 08/08
$308/nighttotal: $616 (2 )
Luce Di Vino
2 4
farm , Montalcino
Luce di Vino is a farm stay located in Montalcino, just 9 miles from the thermal baths of Bagno Vignoni and 14 miles from Mount Amiata. The 270 square foot farm stay features a bedroom, a terrace, a garden, a spa, and a jacuzzi, and can accommodate up to 3 guests.
9.0 34 reviews
Montalcino
07/25 – 07/28
$268/nighttotal: $804 (3 )
Agriturismo La Casella
1 3
gîte , Montalcino
This charming farm stay is located just outside Montalcino, a short walk from the Fortress of Montalcino and the Civic and Diocesan Museum of Sacred Art. Guests rave about the excellent user ratings, highlighting the property's comfortable accommodations and convenient location. The rural retreat features a restaurant, a swimming pool, and a garden with barbecue grills. Guests can enjoy free Wi-Fi, parking, and laundry facilities, as well as tour/ticket assistance for exploring the region.
9.8 94 reviews
Montalcino
07/25 – 07/28
$395/nighttotal: $1185 (3 )
Tenuta Canina
3 3
house , Montalcino
Tenuta Canina is a peaceful retreat located 24 miles from Piazza del Campo in Montalcino and 11 miles from Bagno Vignoni, offering a tranquil escape in the Tuscan countryside. The property has received excellent ratings for location, cleanliness, and user experience. This 3-bedroom vacation home can comfortably accommodate up to 8 guests. Enjoy features like a private pool, open-air bath, fully equipped kitchen, shared kitchen, fireplace, free Wi-Fi, private parking, and a mini-market on-site.
8.6 262 reviews
Montalcino
07/26 – 08/02
$203/nighttotal: $1421 (7 )
Croce Di Mezzo
1 3
farm , Montalcino
The Croce di mezzo farm stay is located in the countryside near Montalcino, about 14 miles from Mount Amiata and 17 miles from Piazza del Campo in Siena. This family-friendly farm offers a seasonal outdoor pool, free Wi-Fi, private parking, barbecue facilities, and well-equipped kitchens in each unit.
9.4 62 reviews
Montalcino
07/11 – 07/12
$199/nightfor 1 night
La Casa Gialla Di Buonconvento
1 3
house , Buonconvento
La Casa Gialla di Buonconvento, a 1-bedroom house rental in the Tuscan countryside, is conveniently located 18 miles from Siena’s Piazza del Campo and 14 miles from Bagno Vignoni, offering easy access to major attractions. This 480-square-foot (approximately 45-square-meter) vacation home sleeps up to 8 guests and includes amenities such as free Wi-Fi, air conditioning, parking, and a fully equipped kitchen; accessibility features are also available.
9.3 3 reviews
Montalcino
08/07 – 08/17
$304/nighttotal: $3040 (10 )
Casalilla Brunello Vineyards
2 3
gîte , Montalcino
This Montalcino vacation rental, a two-bedroom, two-bathroom gîte, offers excellent guest ratings and is conveniently located near Montalcino's historic center, though the precise address isn't provided. The 4-guest apartment features a fully equipped kitchen with a refrigerator and dishwasher, air conditioning, a private garden, access to a seasonal heated pool and hot tub (40°C/104°F), Wi-Fi, and parking; small pets are allowed with an additional fee.
Montalcino
08/09 – 08/15
$1248/nighttotal: $7488 (6 )
150 M² Villa ∙ 3 Bedrooms ∙ 6 Guests
3 4
house , Montalcino
This three-bedroom, three-bathroom villa is located in Montalcino's historic center, steps from shops and the 14th-century fortress, with easy access to Abbazia di Sant'Antimo (6 miles), Bagno Vignoni (11 miles), Pienza (14 miles), Montepulciano (24 miles), and Siena (28 miles). The 1700-square-foot house features a private garden, outdoor Jacuzzi, furnished terrace, private parking, and free Wi-Fi; it comfortably sleeps six guests and includes electric bicycles for exploring the Tuscan countryside, plus access to discounted meals and wine tastings at a nearby owner-run wine bar and private wine tasting lessons in the fortress.
9.0 1933 reviews
Montalcino
07/11 – 07/12
$518/nightfor 1 night
Le Ragnaie
2 3
farm , Montalcino
Le Ragnaie is a country farm located just 1.9 miles from the charming town of Montalcino, offering breathtaking views of the Orcia Valley. Guests consistently praise the farm's excellent location, cleanliness, and overall experience. The farm features elegant apartments with modern comforts and private terraces. Guests can enjoy the swimming pool, relax in the garden, and savor the farm's own wine and olive oil.
9.5 55 reviews
Montalcino
08/06 – 08/08
$324/nighttotal: $648 (2 )
Villa Stella
2 4
house , Montalcino
VILLA STELLA is located in Montalcino, a short drive from both Mount Amiata and Piazza del Campo in Siena, offering easy access to the region’s scenic beauty and cultural attractions. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience. This two-bedroom villa provides 1080 square feet of comfortable living space, accommodating up to four guests. VILLA STELLA offers a fully equipped kitchenette, a relaxing living room with a flat-screen TV, free Wi-Fi, and a peaceful garden with scenic views, perfect for enjoying a relaxing getaway in the Tuscan countryside.
9.4 82 reviews
Montalcino
07/17 – 07/19
$220/nighttotal: $440 (2 )
Casa Costa Delle Caserme
1 2
apartment , Montalcino
CASA COSTA DELLE CASERME is a peaceful apartment in Montalcino, just 26 miles from Piazza del Campo and 26 miles from Mount Amiata, offering easy access to both the historic center and the natural beauty of the surrounding countryside. The apartment consistently receives excellent ratings for cleanliness, location, and user experience. The apartment features one bedroom and one bathroom, accommodating up to two guests in its 650 square foot space. Amenities include a fully equipped kitchen, a shared lounge, free Wi-Fi, and bicycle rentals for exploring the Tuscan countryside.
Guest-Favorite Holiday Houses with Swimming Pool in Montalcino
Having a pool at your Montalcino vacation home lets you enjoy a refreshing dip after the mountains without any extra planning.
8.6 66 reviews
Montalcino
08/06 – 08/08
$301/nighttotal: $602 (2 )
Agriturismo Sant'agostino
2 4
farm , Montalcino
Agriturismo Sant'Agostino, a renovated farmhouse near San Giovanni d'Asso, is located about 16 miles from Bagno Vignoni and 26 miles from Siena's Piazza del Campo, offering easy access to Tuscan attractions. This pet-friendly rental boasts a swimming pool, a terrace, a garden, free Wi-Fi, and private parking, along with air conditioning and a kitchen equipped with a refrigerator and dishwasher in some units.
9.6 19 reviews
Montalcino
08/07 – 08/17
$212/nighttotal: $2120 (10 )
Agriturismo Podere Santo Stefano
1 3
farm , Cinigiano
Agriturismo Podere Santo Stefano is located in Cinigiano, 23 miles from Mount Amiata and 26 miles from Bagno Vignoni, with Florence Airport 78 miles away. This farm stay offers air-conditioned rooms with private entrances, free WiFi, free parking, facilities for disabled guests, and selected rooms with a private terrace, plus an on-site restaurant, bar, outdoor swimming pool, and garden.
9.5 253 reviews
Montalcino
06/27 – 06/28
$472/nightfor 1 night
Borgo Canalicchio Di Sopra Relais
2 2
farm , Montalcino
Borgo Canalicchio is a charming farm stay just one mile from the historic town of Montalcino, nestled in the peaceful Val d'Orcia Valley. The property has consistently earned excellent ratings for its location, cleanliness, and overall experience. The farm offers comfortable apartments with full kitchens and air conditioning. Guests can enjoy two outdoor pools, a spa, a Jacuzzi, and a terrace, as well as the opportunity to taste the farm's own Brunello wine.
Montalcino
08/07 – 08/17
$13309/nighttotal: $133090 (10 )
Villa In Montalcino With 11 Bedrooms Sleeps 22
11 3
house , Montalcino
This Montalcino villa, a 15-minute walk from the Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino, and within 3 miles of Tenuta Greppo and Capanna di Cencioni, offers convenient access to major attractions. This eleven-bedroom, thirteen-bathroom home boasts a private pool, garden, terrace, parking, and sleeps up to 22 guests, featuring a fully equipped kitchen with modern appliances and free Wi-Fi.
Best Montalcino houses with a kitchen
9.1 20 reviews
Montalcino
08/06 – 08/08
$402/nighttotal: $804 (2 )
Casa Al Colle Buonconvento
3 4
house , Buonconvento
Casa Al Colle Buonconvento is a 3-bedroom rental located in Buonconvento, Tuscany, approximately 14 to 19 miles from Parco dei Mulini, Palazzo Chigi-Saracini, National Picture Gallery Siena, and Piazza del Campo. This 1400-square-foot vacation home accommodates up to 16 guests and features a microwave oven, free WiFi, and private parking, with towels and bed linen provided.
9.4 67 reviews
Montalcino
08/06 – 08/08
$504/nighttotal: $1008 (2 )
Borgo Lucignanello Bandini
2 4
house , Montalcino
Borgo Lucignanello Bandini is a vacation home located in the countryside near San Giovanni d'Asso, about 3 miles from its center, and is 17 miles from Montepulciano and a 50-minute drive from Siena. This family-friendly house has a fully equipped kitchen, a free outdoor pool, a garden with BBQ facilities, a fireplace, a fitness center, and a terrace, and can accommodate families or groups of travelers seeking a relaxing Tuscan experience.
10 13 reviews
Montalcino
08/11 – 08/12
$1479/nightfor 1 night
Palazzo Tamanti - 4br 6 Bath Estate Home In Montalcino Center
4 2
house , Montalcino
Palazzo Tamanti, a recently renovated villa in Montalcino, Italy, is located 26 miles from Mount Amiata and 27 miles from Piazza del Campo in Siena. This 4,310-square-foot luxury rental boasts four bedrooms, six bathrooms, and accommodates up to twelve guests, featuring amenities such as a fully equipped kitchen, private parking, Wi-Fi, and a terrace with stunning city views.
Montalcino
08/06 – 08/08
$395/nighttotal: $790 (2 )
130 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 4
house , Buonconvento
Casa Al Colle is a spacious 1400 square feet vacation rental located in Buonconvento, offering a peaceful retreat with convenient access to local attractions. This pet-friendly house accommodates up to 8 guests and features a well-equipped kitchen, high-speed Wi-Fi, and private parking for up to 3 vehicles.
Frequently Asked Questions about villa rentals in Montalcino
What are the must-see attractions in and around Montalcino?
Montalcino is known for its beautiful medieval walls and the Fortezza, a 14th-century fortress that offers panoramic views of the surrounding countryside. You should also visit the historic center with its charming cobblestone streets and the Duomo, a beautiful cathedral. Just outside of Montalcino, you'll find the Abbey of Sant'Antimo, a 12th-century abbey that's a must-see for architecture and history buffs.
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, including wild boars, deer, and foxes. You might also see some birds of prey, such as hawks and falcons, soaring overhead. If you're lucky, you might even spot a rare golden eagle in the hills.
What are the best villa rentals with a pool in Montalcino?
The best time to visit Montalcino is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and the prices are lower. Of course, if you're a wine lover, you'll want to visit during 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 in Montalcino is during the off-season, from November to March. You'll have a wider selection of properties to choose from and you'll likely get a better rate. Just be aware that some businesses might be closed during this time.
What are the best villa rentals for families and kids in Montalcino?
There are many beautiful hiking trails in the area around Montalcino. One popular trail is the Sentiero del Brunello, which follows the route of the Brunello di Montalcino wine trail. Another great option is the Sentiero del Parco Naturale della Val d'Orcia, which takes you through the stunning Val d'Orcia landscape.
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 gives you the privacy and space you need to relax and enjoy your vacation. It also gives you the opportunity to cook your own meals and experience the local culture at your own pace. You'll have the flexibility to come and go as you please, and you'll often have access to amenities that you wouldn't find in a hotel, such as a private pool or garden.
What are the best villa rentals with parking in Montalcino?
Yes, there are many popular destinations near Montalcino. A short drive away is Siena, a beautiful medieval city known for its stunning Piazza del Campo. You can also visit the charming hilltop town of Pienza, known for its Renaissance architecture and delicious Pecorino cheese. Or, if you're interested in wine, you can visit the nearby wineries of Montepulciano and Chianti.
Destinations nearby
Best Montalcino houses with a fireplace
8.8 45 reviews
Montalcino
07/09 – 07/10
$224/nightfor 1 night
Agriturismo Villa Paradisino Musico
1 2
farm , Montalcino
Agriturismo Villa Paradisino MUSICO, near Montalcino, Tuscany, offers a convenient location, 13 miles from Bagno Vignoni and 26 miles from Mount Amiata. This 170-square-foot (approximately 16-square-meter) rural lodging boasts one bedroom, four bathrooms, and accommodates eight guests, featuring a pool, bar, and free Wi-Fi.
10 2 reviews
Montalcino
08/07 – 08/17
$2114/nighttotal: $21140 (10 )
Il Colle Di Donna Ilaria 12, Emma Villas
6 3
house , Buonconvento
Il Colle Di Donna Ilaria 16, near Buonconvento, Italy, is ideally located 21 miles from Siena's Piazza del Campo and 19 miles from Bagno Vignoni. This 5,380-square-foot vacation home boasts 8 bedrooms, 8 bathrooms, a private pool, and amenities including free Wi-Fi, parking, and an EV charging station.
Montalcino
08/07 – 08/17
$2103/nighttotal: $21030 (10 )
500 M² Villa ∙ 6 Bedrooms ∙ 12 Guests
6 3
house , Buonconvento
Il Colle di Donna Ilaria, a large farmhouse estate near Buonconvento, enjoys a secluded location in the Val d'Orcia, about a 30-minute drive from Siena and minutes from the Abbey of Monte Oliveto Maggiore. This 5,700-square-foot vacation rental boasts eight bedrooms, eight bathrooms, and accommodates up to 16 guests, featuring a private pool (open April-October), a terrace, and a sizable garden, plus amenities such as Wi-Fi, a full kitchen, and ample parking.
10 2 reviews
Montalcino
08/07 – 08/17
$365/nighttotal: $3650 (10 )
Casa Maria - Modern Home Near Montalcino
3 3
house , Montalcino
Casa Maria - Country Loft, a 1940 sq ft vacation home, is located in Castelnuovo dellʼAbate, offering a peaceful countryside setting just a short drive from Montalcino, a town celebrated for its Brunello wine and historic sites. This spacious 3-bedroom, 3-bathroom accommodation accommodates up to 11 guests and features air conditioning, free WiFi, a full kitchen, a fireplace, a garden, and a terrace with mountain views, with airport transfer services available.
Best Montalcino villas and beach houses with jacuzzi
8.8 11 reviews
Montalcino
08/07 – 08/17
$206/nighttotal: $2060 (10 )
Agriturismo Piombaia
1 3
gîte , Montalcino
This Montalcino farmhouse rental is conveniently located near the Tenuta Greppo Franco Biondi Santi winery (1 mile) and the Abbazia di Sant'Antimo abbey (4.7 miles), offering a tranquil suburban setting. The property features a swimming pool, Jacuzzi, terrace, and garden, plus free Wi-Fi, parking, and a complimentary breakfast buffet; housekeeping is available upon request.
Montalcino
08/09 – 08/15
$3739/nighttotal: $22434 (6 )
Tenuta Bosco Di Pietra
1 4
gîte , Montalcino
Tenuta Bosco di Pietra is a restored Tuscan farmhouse situated in the countryside just outside Montalcino, offering 180-degree views of the Val d'Orcia hills and vineyard vistas. This luxurious villa accommodates up to 10 guests with 5 bedrooms and 5 bathrooms, featuring a gourmet kitchen with high-end appliances, air conditioning, a swimming pool, and a Jacuzzi on an expansive terrace perfect for al fresco dining.
9.6 196 reviews
Montalcino
08/06 – 08/08
$597/nighttotal: $1194 (2 )
Tenuta Castelgiocondo
2 4
farm , Montalcino
Tenuta CastelGiocondo, a Montalcino farmhouse stay, is located 27 miles from Siena's Piazza del Campo, 17 miles from Bagno Vignoni, and 31 miles from Mount Amiata, offering easy access to Tuscany's major attractions. This 220-square-foot (approximately 20-square-meter) farmhouse rental features one bedroom, one bathroom, accommodates up to three guests, and includes amenities such as a Jacuzzi, sauna, and free Wi-Fi.
9.3 4 reviews
Montalcino
08/06 – 08/08
$467/nighttotal: $934 (2 )
Casale Il Gugnolo
4 4
house , Castiglione d'Orcia
Casale il Gugnolo is a house located in Castiglione d'Orcia, 1.9 miles from Bagno Vignoni and 20 miles from Mount Amiata. This 2150 sq ft villa accommodates up to 15 guests with 4 bedrooms, 3 bathrooms, a full kitchen, hot tub, garden, and terrace, offering bike rentals and an interior fireplace.