
Villa vacation rentals in Montalcino
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Top-rated villa rentals in Montalcino
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Popular amenities for Montalcino villa rentals
Villa rentals with a pool

Tuscany Villa Mammi
Absolutely brilliant place. Very charming, spacious and calm. Beautiful view, pool, and outdoor area. Simone is very kind and highly responsive. We stayed here 6 adults and had a wonderful time. Highly recommended for both friends and families.

Stunning Tuscan Villa & Panoramic Infinity Pool
This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.

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!

Podere la Piscina Termale – RestArt
Perfect stay from start to finish. The villa was immaculate and the staff who checked us in were fast, considerate and friendly. They informed us of extra services that we ended up using in the end like we organised a dinner with their private chef on our last night and it was amazing. The thermal pool and sauna were TOP! Highly recommend and will book again!

The Lazy Oak
We (2 couples) had a wonderful time at the Lazy Oak Villa. The booklet in the house had great recommendations for dinner in Loro Ciuffenna. We did wine tastings at 2 family vineyards located very close to the villa- Morandi Organic Winery with Denis and Società Agricola Caspriano with Simona. Highly recommend both. One of our couples was celebrating an anniversary and Mario arranged for a chef to come to the villa and prepare a traditional Tuscan meal. It was beyond words! The pool was pristine and such a great bonus with the summer heat.

Terra Antica Suite & Ville - Montepulciano
Beautiful property. Staff were amazing, responsive and friendly. Location ideal for visiting other cities by car. Exactly as pictured. Breakfast which was added on a day to day basis was spectacular. Very relaxing sitting on patio and by the pool.

Villa Fortuna with Hot-Tub and pool near Tuscany
A Perfect Holiday – Like Heaven on Earth! This place exceeded all our expectations. A stunning and peaceful location with breathtaking views over the valley, lake, and mountains. The house and garden were beautifully maintained, and the accommodation was very clean and comfortable. A special thank you to Mrs. Lesley, who was an invaluable help throughout our stay. She provided us with plenty of useful tips and advice on various matters, such as train tickets and local attractions. Thanks to her, we were also able to arrange a wonderful dinner at the villa – truly an unforgettable experience. We wholeheartedly recommend this place – if we could give it 150%, we absolutely would!

SacroFanum Villa
We had a wonderful time at the villa! The view of the Tuscan countryside and Scrofiano is simply stunning. The pool was a real highlight: well-maintained, quiet and perfect to unwind. Manola and Martha were very friendly and helpful, available for any questions at any time. Overall, an all-round relaxing time – we'll be back for sure!
Private villa rentals

Scacciapensieri. Cottage in Tuscan Country
Great holiday home with beautiful views over the Tuscan hills. No less than 3 spacious bedrooms with great beds. A nice covered terrace with the same beautiful view where you can have delicious breakfast or dinner. The private swimming pool is of course also fantastic, our children enjoyed this. Gabriele is a very friendly proactive host who sent all nice tips and useful info in advance and awakened our self upon arrival. Despite the slightly inclement weather during the week we were there, there is plenty to do and visit in the area, when the weather is nice you can also go to the coast. I would highly recommend this stay and hope to come back someday!

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.

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!

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.

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.

Romantic Villa with private pool - "Il Pollaio"
A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!

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

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 Febea - Villa Febea 16
Villa Febea is the most magical place, perfect for a large family gathering and celebration. It is gorgeous, comfortable, practical and in a great location. We were given first-class treatment and felt at home and well taken care of. We were given guidance and advice on the planning of our stay over the course of many months, so when we arrived at the villa, everything fell into place perfectly. The owners offer a large selection of services and excursions and can help with just about anything. We had fantastic dinners organized for us at the villa, and we highly recommend the pasta making class followed by dinner, which was one of many highlights. We loved the place, the staff and our whole experience. A holiday and celebration to remember forever!

Villa Polvese Luxury Lake side Villa
The villa is the most beautiful place we stayed at during our 20 day trip through Europe. It’s a bit on a splurge in price but very much worth it. The views from the villa of the pool and the lake are breathtaking. The house is very beautiful, everything was functioning properly and the kitchen is great to cook in. We stayed in and cooked dinner one night and it was great. We also took advantage of the Complimentary olive oil tasting that is included with the stay and that was also of fun. Our guide said was so knowledgeable! I can’t say enough good things about this place. It was a much needed break during our busy vacation.

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!

Podere la Pompa
I stayed with my family at Maria's beautiful house in the countryside north of Grosseto. The property is idyllic, tucked away between the trees with virtually no line of sight to other houses or buildings. The home is modern (although the architecture is very traditional) and the furnishings are of very high quality. The outdoor pool area is perfect for an evening cocktail or just to lounge during the day. I cannot recommend Maria's home highly enough and I look forward to visiting again!

Villa Isabella
Wow! Christina’s property is beautiful! The surrounding Tuscan hills make for a breathtaking setting, with wonderful views to the east and west for sunrise and sunset. We enjoyed drinking in the views from the terraces and while cooling off in the pool, which was a great size and bigger than we had imagined from the pictures. Watching the local swallows, who would soar overhead and drink from the pool, was a real treat. The villa itself was spacious, clean and thoughtfully decorated. Christina was a wonderful host, ready to greet us on arrival and to help us check-out, and responsive to all our messages. She even bought us a lilo for the pool when I asked if there was one! Christina had lots of suggestions of local things to do, from the best artisanal butcher from whom to purchase bistecca alla fiorentina, to where to buy the finest locally produced olive oil and Chianti. We hope to return, a real treat! Grazie mille, Christina!

Tuscan farmhouse with private pool and views
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann

L’Apparita del Peruzzi, pool, super view, save30% 7d +
An enchanting place. The villa is steeped in history and the gardens with a small amphitheater and a distant view of Siena are spectacular. Great location from which to explore the rest of Tuscany. My family and I have enjoyed our stay.
Quick stats about villa rentals in Montalcino
Total rentals
100 properties
Nightly prices starting at
G$20,910 GYD 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
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- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Gulf of Baratti
- Cala Violina
- Kite Beach Fiumara
- Marina di Grosseto beach
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Tenuta Le Velette
- Santa Maria della Scala
- Casa Barthel
- Cantina Stefanoni
- CavallinoMatto
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Pubblico Palace
- Castiglion del Bosco Winery
- Golf Club Toscana
- Riva del Marchese
- Podere La Marronaia, Sosta alle Colonne
- Cantina Contucci
- Cantina de' Ricci
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