Search vacation rentals in Montalcino from 100+ sites!

152 available vacation rental offers

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

Best Vacation rentals and Airbnb offers in Montalcino

Best Montalcino vacation rentals with a balcony

Borgo Canalicchio Di Sopra Relais - Montalcino
9.4 242 reviews

Borgo Canalicchio Di Sopra Relais

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.
Azienda Agraria La Casella - Montalcino
9.0 235 reviews

Azienda Agraria La Casella

farm, Montalcino
Azienda Agraria La Casella is located just a 5-minute walk from the center of Montalcino, a charming town in Tuscany, and is about 25 miles from Siena. Guests consistently rate the location, cleanliness, and overall experience as excellent.
The farm offers a variety of accommodation options, including apartments designed in a traditional Tuscan style. Guests can enjoy amenities such as a garden, BBQ facilities, and a restaurant serving authentic Tuscan dishes, as well as explore the surrounding area for hiking and wine tasting.
Azienda Agricola A Bonacchi - Montalcino
9.2 5 reviews

Azienda Agricola A Bonacchi

farm, Montalcino
Agriturismo Bonacchi is located in the Montalcino area of Tuscany, a short drive from Siena, Montepulciano, and Chianciano Terme, offering easy access to vineyards, wineries, and stunning landscapes. This farm stay has received very good user ratings, excellent location ratings, and very good cleanliness ratings.
The apartments feature wood-beamed ceilings and terracotta tiles, creating a charming and authentic Tuscan ambiance. Guests can enjoy the farm's wine production, relax on their private terrace, and take advantage of modern amenities like flat-screen TVs, air conditioning, and kitchenettes.
Croce Di Mezzo - Montalcino
8.4 2 reviews

Croce Di Mezzo

farm, Montalcino
Farm with a good rating of 84% based on 2 reviews. Your accommodation will be located in Montalcino.
Facilities and services include a barbecue, a swimming pool and air conditioning. Take advantage of the terrace in this accommodation in Montalcino.

Our Favorite Family-Friendly Vacation Rentals in Montalcino

Plan a family mountain retreat in these spacious Montalcino rentals surrounded by trails and fresh air.

Apartment 'Rocci Al 17' With Mountain View And Wi-fi - Montalcino
No reviews

Apartment 'Rocci Al 17' With Mountain View And Wi-fi

apartment, Montalcino
This Montalcino apartment rental is centrally located, within a 15-minute walk of a tennis court and close to the Fortress of Montalcino, the Civic and Diocesan Museum of Sacred Art, and the Museum of Brunello.
This 600-square-foot (56-square-meter) two-bedroom, one-bathroom unit sleeps four, features a well-equipped kitchen with a fridge and microwave, high-speed Wi-Fi, and offers free parking nearby at Hotel Oliviera; a baby cot is available upon request.
Podere Belsogno - Montalcino
9.4 281 reviews

Podere Belsogno

apartment, Montalcino
Podere Belsogno is a two-bedroom apartment located in Montalcino, Tuscany, a short 12-mile drive from Bagno Vignoni and a 26-mile drive from Siena's Piazza del Campo. The apartment features a private entrance, an outdoor dining area, a terrace with mountain views, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher.
Croce Di Mezzo - Montalcino
8.4 211 reviews

Croce Di Mezzo

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.
Apartment 'Casa Francesca' With Hills View & Courtyard - Montalcino
10 3 reviews

Apartment 'Casa Francesca' With Hills View & Courtyard

apartment, Montalcino
This apartment is located in the mountains of Montalcino, a short walk from the Civic and Diocesan Museum of Sacred Art and the Fortress of Montalcino, offering stunning views and a peaceful atmosphere. It has received excellent user ratings for its comfort and convenience.
The 750-square-foot apartment comfortably accommodates up to 6 guests with 2 bedrooms and a sofa bed. It features free Wi-Fi, a fireplace, a fully equipped kitchen, a terrace or balcony, a garden, parking, and designated smoking areas, as well as games for entertainment.

Frequently Asked Questions about vacation rentals in Montalcino

  • What are some interesting places to visit in or near Montalcino?

    Montalcino is known for its stunning views and historic sites. You can't miss the Fortezza di Montalcino, a 14th-century fortress offering panoramic views. The historic center is also a must-see, with its charming streets and medieval architecture. For a day trip, visit the nearby town of Pienza, known for its Renaissance architecture and delicious Pecorino cheese.
  • What are the best Airbnb and vacation rentals in Montalcino?

    Charming House In Montalcino With City View, Panoramic Country Suite Montalcino and Montalcino - Casa Gelsomino - Giardino E Relax are the most popular Airbnb and vacation rentals in Montalcino among travelers.

  • Which walking or cycling routes are the best in Montalcino?

    The area around Montalcino is perfect for exploring on foot or by bike. One popular route is the Sentiero del Brunello, a scenic trail that winds through vineyards and olive groves. For a more challenging ride, try the challenging climb up to the top of Monte Amiata, offering breathtaking views of the surrounding countryside.
  • What are the most popular Airbnbs in Montalcino?

  • What sports or outdoor activites can visitors enjoy in and around Montalcino?

    Montalcino is a great place for outdoor enthusiasts. You can go hiking, mountain biking, and horseback riding in the surrounding hills. The area is also known for its excellent wine tasting, so be sure to check out some of the local wineries. For a more relaxing experience, take a dip in the natural hot springs at Bagni San Filippo.
  • What are the best vacation rentals with a pool in Montalcino?

    Panoramic Country Suite Montalcino, Agriturismo Collodi and Tenuta Canina are the best vacation rentals with a pool in Montalcino.

  • What other towns or cities can be easily accessed from Montalcino?

    Montalcino is well-connected to other towns in Tuscany. You can easily reach Siena, Florence, and Rome by car or train. For a shorter trip, consider visiting the nearby towns of Pienza, Montepulciano, and San Quirico d'Orcia, all of which are known for their beauty and charm.
  • What are the best rentals for families and kids in Montalcino?

  • What amenities are commonly available in vacation rentals in Montalcino?

    Vacation rentals in Montalcino typically offer a range of amenities, including kitchens, bathrooms, bedrooms, and living areas. Many rentals also have private patios or gardens, as well as access to swimming pools or hot tubs. Some rentals may also offer additional amenities such as laundry facilities, Wi-Fi, and parking.
  • What are the best rentals or Airbnbs with a jacuzzi in Montalcino?

  • What time of year is best to rent a vacation rental Montalcino?

    The best time to visit Montalcino is during the shoulder seasons, from April to May or September to October. The weather is pleasant and the crowds are smaller. You can also enjoy the harvest season in the fall, when the vineyards are bursting with grapes and the air is filled with the aroma of wine.
  • What are the local dishes in Montalcino region?

    Montalcino is known for its delicious cuisine, especially its traditional dishes like pici, a thick hand-rolled pasta, and ribollita, a hearty bread soup. The region is also famous for its Brunello di Montalcino wine, a full-bodied red wine made from Sangiovese grapes. Be sure to try the local pecorino cheese, a sheep's milk cheese that is produced in the area.

Popular destinations

Best Montalcino vacation rentals with a fireplace

Agriturismo Villa Paradisino Musico - Montalcino
9.1 69 reviews

Agriturismo Villa Paradisino Musico

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.
Montalcino Townhouse With Private Garden & Spa - Montalcino
10 154 reviews

Montalcino Townhouse With Private Garden & Spa

apartment, Montalcino
This one-bedroom house is located in the upper part of Montalcino, just a short walk from the main square and the cathedral. The house features a fully equipped kitchen, a wine cellar, a jacuzzi, a sauna, a steam bath, a large garden with a gazebo, and panoramic views of the surrounding countryside.
60 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests - Montalcino
9.6 1 review

60 M² Apartment ∙ 2 Bedrooms ∙ 6 Guests

apartment, Montalcino
Casa Vacanze del Borgo, a two-bedroom apartment rental in Montalcino, Italy, is located 150 meters from the Bordi Santi winery and 3 kilometers (1.9 miles) from Montalcino's town center, offering easy access to shops and historical sites.
This 650-square-foot (60-square-meter) vacation rental sleeps up to six guests and features a fully equipped kitchen with a dishwasher, private garden, covered terrace with vineyard views, free parking, Wi-Fi, and a washing machine.
Colle Al Matrichese - Historic Winery - Montalcino
9.3 110 reviews

Colle Al Matrichese - Historic Winery

house, Montalcino
This Montalcino vacation home, located in Colle al Matrichese, is 25 miles from Piazza del Campo in Siena and 26 miles from Mount Amiata, offering easy access to Tuscany's renowned wine region.
The property features a fully equipped kitchen, private parking, Wi-Fi, a terrace, garden, on-site massage services, and bicycle rentals for exploring the picturesque Tuscan countryside.

Best Montalcino vacation rentals with a sauna

N° 24 - Montalcino
9.7 71 reviews

N° 24

apartment, Montalcino
This charming Tuscan apartment in Montalcino's historic center is just a short walk from the main square and the renowned Brunello di Montalcino wine cellars. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This one-bedroom apartment comfortably sleeps four guests, with two bathrooms and a spacious living area. Enjoy modern amenities like a fully equipped kitchen, three internet TVs, Wi-Fi, and a Bluetooth HIFI system, along with breathtaking views of the Val d'Orcia from the bedrooms.

Search 5-Star Vacation Rentals in Montalcino

Enjoy 5-star comfort and mountain views at these luxury vacation rentals in Montalcino, curated for total relaxation.

La Casa Di Annetta - Montalcino
10 5 reviews

La Casa Di Annetta

apartment, Montalcino

Find the Best Dog-Friendly Vacation Rentals in Montalcino

These dog-friendly vacation rentals and Airbnbs in Montalcino offer vast space and easy access to local hiking trails.

Emotions Appartamento Con Terrazza - Montalcino
9.8 22 reviews

Emotions Appartamento Con Terrazza

apartment, Montalcino
Montalcino Lavanda Apartment - Montalcino
9.1 18 reviews

Montalcino Lavanda Apartment

apartment, Montalcino
Apartment In The Mimosa Hamlet - Montalcino
9.5 41 reviews

Apartment In The Mimosa Hamlet

apartment, Montalcino
Apartment With A View In Montalcino - Montalcino
No reviews

Apartment With A View In Montalcino

apartment, Montalcino

Traveler-Approved Vacation Rentals with a Pool in Montalcino

A vacation rental with a pool in Montalcino provides a refreshing dip to cool off after a day of hiking.

Appartamento Edera - Montalcino
10 2 reviews

Appartamento Edera

apartment, Montalcino
Villa Brunello - Twelve Bedroom Villa, Sleeps 24 - Montalcino
No reviews

Villa Brunello - Twelve Bedroom Villa, Sleeps 24

house, Montalcino
Apartment ∙ 1 Bedroom ∙ 2 Guests - Montalcino
No reviews

Apartment ∙ 1 Bedroom ∙ 2 Guests

apartment, Montalcino
Le Ragnaie - Montalcino
9.2 952 reviews

Le Ragnaie

farm, Montalcino

Popular Vacation Rentals with Jacuzzi in Montalcino

Relax in a hot tub at these exclusive Montalcino vacation rentals and Airbnbs, designed for total tranquility.

Villa Le Prata - Residenza Del Vescovo - Montalcino
9.8 109 reviews

Villa Le Prata - Residenza Del Vescovo

resort, Montalcino
©2026 cozycozy.com