
Villa vacation rentals in Montalcino
Find and book unique villas on Airbnb
Top-rated villa rentals in Montalcino
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Montalcino villa rentals
Villa rentals with a pool

Sestuccina
We spent part of our Honeymoon staying at this beautiful villa and quite honestly, we could not have picked a more perfect place. Check in was quick and easy. We met Luciano’s daughter, Birgitta on site and she talked us through the villa and all nearby amenities we may need. She was extremely kind and helpful. The little village is close by and the villa has everything you need to cater for yourselves and have a completely private get away. We cannot recommend enough. The villa was beautifully clean and the surroundings were stunning.

Case Bianchi
We had a great time! Super clean and spacious house with a nice outdoor area. Constanze was always super helpful and responded quickly. But be aware, you need a car and restaurants and supermarkets are not in walking distance. Thanks a lot for having us.

La Bacaia
We thoroughly enjoyed our stay. The house is conveniently located in the heart of the Valdichiana with easy and clear access to the surrounding towns. The grounds were beautifully landscaped with a combination of olive trees, grapevines, flowers and even herbs like rosemary, basil and mint that we used in our cooking. The rooms were spacious and very private. Our group of 6 were more than comfortably accommodated, each with its own bathroom and AC units that worked well. The two kitchens served us well. We mainly utilized the outside kitchen as the weather throughout our stay was perfect. The kitchens were well stocked with all of the necessary cooking items. There were some items that we needed to purchase at the local supermarket, including shower gel, paper towels, napkins, etc. For a one week stay we would recommend extra towels, especially for the pool. Overall, I would highly recommend La Bacaia as a base to fully enjoy your Tuscan vacation.

Montemarcoli
We had an amazing stay at the villa. A modern house in quiet surroundings with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.

Luxury Tuscan countryside villa with pool/WiFi/AC
Family loved the villa and pool. The closest village is only a few minutes away and has stunning views. There's a great butcher in town as well.

Casa Boschetto, villa with private pool
Cases Nucci was a magnificent place. The views are amazing. The history behind the property was so cool. Ricardo was so nice and helpful from checking in, recommendations, and showing us around. I would love to come back here again. What a hidden gem!

The twigs
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏

Unique Villa in Tuscany
An absolutely stunning Villa in beautiful Tuscany that is just perfect! Luc and Sara are wonderful hosts. Extremely friendly, full of local knowledge and recommendations and always available to answer questions. Luc even acted as our Taxi service in not only recommending a fabulous vineyard to visit for a private tour, but taking us there and picking us up too so we could fully enjoy all the magnificent wines on offer! Sara's Tiramisu is legendary and the good news is the kitchen in the villa is so well appointed you have everything you need to try making it yourself too! Before visiting we wondered if the Villa could possibly match up to the pictures and the reviews - it 100% does in every way and is without doubt the best Air BnB we have ever stayed in. Thanks Luc, Sara, Lucky and all the cats for making our stay so special - we will be back!
Private villa rentals

Tuscany Villa Mammi
Simone was a truly fantastic host. He was always so friendly, eager to help, and checked in with us every few days to make sure everything was okay, but never to the point it felt like it was encroaching on our privacy. Both check in and check out were super easy. The villa and its surroundings are absolutely stunning. I’d go as far to say it’s the best airbnb I have stayed in. The photos don’t show just how many areas there are on different levels which is great if you like to have a bit of privacy or different views every now and then. We loved watching the sunset over Tuscany each night. If you find steep hills a bit of a challenge, you may have difficulty walking to/from town, but this is no problem if you’ve hired a car. Thanks so much, Simone!

Spacious Panoramic Villa: Perfect to Visit Tuscany
I honestly can't say enough positive things about this beautiful villa/property and the host (Andrea). It exceeded all expectations. The pictures are beautiful, but it truly doesn't do justice to the real thing. The villa is huge with 4 very spacious bedrooms / 3 full baths that provides tons of space. The living room is huge with an incredible view and so much other room (dining, sitting area, etc). The outside patio is unbelievable with a view to die for. Has a private garage for a car if you drive and washing machine. Kitchen is good size with full-size appliances if you choose to cook. Air conditioning in all rooms! Andrea was an exceptional host and extremely accommodating. He met us when we arrived and gave us a personal tour and also left us with a delicious bottle of wine! If you take a train to Chiusi (we did), you will have to get a taxi from the station to the villa (~10 minute drive). Chiusi historic center is a very easy 5-minute uphill walk from the villa. 5 *

Villa with pool in Chianti Area
Our stay at Mariella's beautiful home was a highlight of our five week trip throughout Italy. Peacefully situated between Florence and Siena, this villa offers a welcoming respite from the hustle and bustle of the cities. It was also super convenient to the vineyards throughout Chianti. Waking up every morning to the sunrise views over the valley and enjoying a glass of wine in the evening were the perfect beginning and ending to each day. The pool was even larger than we imagined and provided days of entertainment sprinkled in during a week of sightseeing and wine tasting. I cannot recommend this home, location, or host enough. You will NOT be disappointed!

Charming villa 15' walk to center stunning view
Incredible property with a breath taking view over Florence. Hard to put into words how perfect the property is but the best part of the whole experience was the hospitality Marco, Stefania Grinza Carota and Filippo! The best hosts imaginable made us feel so at home, welcome and a part of the family. Now we want to move to Florence

Villa Il Tollino
We had a wonderful stay at this place! Ginacarlo and Gabriella are extremely friendly hosts who have a lot of helpful recommendations and are always very responsive. Moreover, they not only brought us homemade pizza, sweet treats, fruits and wine, they also brought toys for our 1.5year old daughter! The home is clean and has everything you need for your stay. The views from the patio of the surroundings are amazing!! The entire area is also very peaceful and relaxing and close to many interesting locations (Siena, Arezzo, Montepulciano etc). We highly recommend this place and would come back again!

Vakantievilla Farmhouse Dolci Hills
This was the finest AirBNB home that we've ever stayed in. Every room was immaculate, the views were incredible (private and among vineyards, you can see for miles), every appliance and fixture seemed new. Everything was anticipated to make the stay perfect.....a refrigerator, bathroom and shower at the beautiful pool, pool towels in each bedroom, etc. As soon as you walk into this house, you are going to go "wow", and for good reason. Francesca came and cooked us a delicious local dinner and did some light grocery shopping for us.....all for an unreasonably LOW fee. We had another chef team come in on another night. We also visited a local winery where we had a fantastic, private wine tasting tour and lunch (Tenuta Vitalonga) and followed that up with touring Orvieto and having dinner at a very unique restaurant (Le Grotte del Funaro). Make sure you have a car or are using a bus/limo service for your transportation, nothing is walkable from this beautiful private house.

CHARMING TUSCANY VILLA PRIVATE POOL
We had an amazing time in Francesco's place. The house is wondefull. Spacious, clean and very modern. The garden and surroundings are very beautiful. Francesco is an excellent host. He is responsive and his service is ourstanding. He welcomed us with pizza and wine en he even brought us a box with delicious treats for breakfast every morning. I can recommend Francesco's place for everyone who want to stay in a central location to discover Tuscany and stay in a charming house full of luxury. Couldn't be better.

Beautiful Country House, near Siena with jacuzzi
We had a wonderful time at the estate. We were visiting with 4 adults and 2 little babies. The communication with David was always super prompt and he even really quickly helped us out in finding a doctor when our daughter got sick during the stay. The house has everything you need and is well equiped. We cooked every evening in the cosy kitchen and had wonderful breakfasts in the garden. The Jacuzzi overlooking the valley was also a nice spot for relaxing in the warm water. Overall we can just recommend this historic but well modernized house as your idyllic getaway in Tuskany.
Luxury villa rentals

Fabulous Farmhouse with Pool & 360 Panoramic View
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!

Luxury Villa on Chianti Wine Estate
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.

Capanna Di Elfo
The property was comfortable, spacious and spotlessly clean. The owners of the property , Claudio and Angelica, are helpful and delightful. However, the “host” BoMVillas , who acts as a middleman, was rude and disrespectful when we had a miscommunication. I would not make another booking that was offered by BoMVillas.

Luxury Villa in the very heart of Chianti
Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!

villa "La Fonticina"
We had a wonderful stay! The property sits on a stunningly large lot surrounded by trees, which gave it a peaceful and private feel. The pool was a highlight — spacious, clean, and with beautiful views that made every swim feel special. Inside, the decor was tasteful and thoughtfully done, blending comfort with style. Everything was clean and well-maintained. Highly recommend for anyone looking for a relaxing escape in nature without compromising on style!

Podere on the Crete Senesi
We could not have asked for a more beautiful setting to celebrate my partner’s 40th birthday. Our week was perfectly balanced between visiting nearby Montalcino wineries & surrounding villages, a day trip to Siena, and lazing about the pool & villa. Monica was kind, generous & helpful from the time of booking. She accommodated all requests and even left a gift for my partner to celebrate his birthday! Will be back! Would rate this 6 stars if we could.

Villa Blue Melon - private beach
What a lovely property and host! Andrea was very friendly and helpful. He gave us a tour of the home and answered any questions we had before leaving us to enjoy the wonderful property. He even sent us restaurant recommendations which turned out to be amazing. The property itself is picturesque and almost felt unreal. My family was in awe and couldn’t stop mentioning how it was the nicest part of our trip (which we stayed in multiple places throughout). It was impeccably clean without a single speck of dust present. The furnishings were all perfectly picked and each added charm to the home. The rooms were cozy and all had wonderful views. We almost didn’t even notice the weather was gloomy the few days we were there because of how much we enjoyed the home itself. I can only imagine when it’s sunny and warm! Thank you for everything Andrea. We definitely plan to come back!

VILLALADOLCEVITA
Very nice stay for a few days relaxing in summer. Beautiful olive gardens around the house, nice collection of wine. Everything clear, super big house, will come back next year!
Quick stats about villa rentals in Montalcino
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
90 properties have a pool
Destinations to explore
- Florence Vacation rentals
- Pisa Vacation rentals
- Rome Vacation rentals
- Bologna Vacation rentals
- Portofino Vacation rentals
- Riviera di Levante Vacation rentals
- Francavilla al Mare Vacation rentals
- Genoa Vacation rentals
- Italian Riviera Vacation rentals
- Verona Vacation rentals
- Venice Vacation rentals
- Agnone Vacation rentals
- Rentals with an EV charger Montalcino
- Rentals with a fireplace Montalcino
- Rentals with a hot tub Montalcino
- Luxury rentals Montalcino
- Vacation home rentals Montalcino
- Rentals with outdoor seating Montalcino
- Rentals with breakfast Montalcino
- Fitness-friendly rentals Montalcino
- Smoking-friendly rentals Montalcino
- House rentals Montalcino
- Farmstay rentals Montalcino
- Rentals with pools Montalcino
- Pet-friendly rentals Montalcino
- Condo rentals Montalcino
- Rentals with a washer and dryer Montalcino
- Rentals with a sauna Montalcino
- Kid-friendly rentals Montalcino
- Rentals with a patio Montalcino
- Family-friendly rentals Montalcino
- Bed and breakfasts Montalcino
- Apartment rentals Montalcino
- Rentals with a fire pit Montalcino
- Cottage rentals Montalcino
- Villa rentals Province of Siena
- Villa rentals Tuscany
- Villa rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Gulf of Baratti
- Cala Violina
- Kite Beach Fiumara
- Marina di Grosseto beach
- Avignonesi Winery Fattoria Le Capezzine
- Casa Barthel
- Cala Di Forno
- Santa Maria della Scala
- CavallinoMatto
- Tenuta Le Velette
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Pubblico Palace
- Golf Club Toscana
- Riva del Marchese
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cantina de' Ricci
- Castiglion del Bosco Winery
- Podere La Marronaia, Sosta alle Colonne
- Madonna del Latte
- Cantina Contucci
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
- Nature and outdoors Montalcino
- Things to do Province of Siena
- Nature and outdoors Province of Siena
- Sightseeing Province of Siena
- Tours Province of Siena
- Food and drink Province of Siena
- Art and culture Province of Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Food and drink Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Wellness Tuscany
- Sightseeing Tuscany
- Entertainment Tuscany
- Tours Tuscany
- Things to do Italy
- Food and drink Italy
- Tours Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Sightseeing Italy
- Entertainment Italy
- Sports activities Italy