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

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!

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!

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!

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.

Sestuccina
Beautiful place to stay! • super nice location (a lot of nature and very quiet) • Communication always runs smoothly • Great restaurants and delicious ice cream within 5 minutes' drive • Amenities exactly as indicated I would recommend it again and again! Luciano and Brigitta are great hosts 😊

The Lazy Oak
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Private villa rentals

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.

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.

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.

Villa Leopoldina, 6 pax, Private Pool
Gigi’s place is one of the most peaceful places we’ve stayed in in Italy. The location is gorgeous and perfectly located between different towns to explore (Cortona, Arezzo, Montepulciano to name a few). A car is necessary but you can get to the town center for groceries and local produce in 10 minutes. We enjoyed spending our days by the pool, cooking and barbecuing in the garden. The kitchen was the most equipped I’ve ever seen for an Airbnb and the house was spotless. Extra supplies were left for us as well if we needed which was a nice touch. Gigi was always available for recommendations and extremely friendly. If you’re looking for calm and quiet this is your place!!

Villa Il Diaccio with view of the Tuscan Maremma
This house is perfect for a family vacation with so many different amenities. We got the most out of the jacuzzi, pool table, living room campfire and beautiful views down to Roccatederighi along with the mountains and sea in the far distance. The host, Riccardo is so sweet, welcoming and very helpful and responsive to questions I had asked. Experiencing this place is even better in person and all we wanted in a relaxing vacation.
Luxury villa rentals

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!

Terra Antica Suites & Villas – Cervognano
Terra Antica is simply stunning. The room, view, hospitality all exceeded expectations-which were already very high! If you go, definitely do the wine tasting and lunch. Mario was so interesting and informative, the wines are out of this world, and the lunch was delicious. Thanks for a memorable visit. Hope to return again soon!!!

La Vignaccia (Farmhouse) - villa w/private pool
La Vignaccia is wonderful. We were a family of 6 adults plus a baby, and the set up was great for spending time together but also having plenty of space. The kitchen is well equipped for cooking for a large group and the many private spaces were very relaxing. Working remotely was possible with the wifi but not super strong for calls. However there is 5G around the house, so hot spotting from a window worked fine.

Villa Lidia, la Dolce Vita at its Best!
Marleen and Stijn, her property manager, were extremely communicative and ensured we had everything we needed during our stay! They messaged clear instructions and videos and when we arrived everything was so easy and clean! The property is absolutely breathtaking, with gorgeous views. This was the best air bnb experience I have ever had. It was thanks to Marleen’s kindness and clear instructions. My family cannot wait to return to the villa. It was amazing! The property is gated too, so we felt safe and private.

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.

Villa Cristina Tuscany,your dream!!
Absolutely beautiful property with spectacular views. Wonderful setting for a relaxing holiday. Minutes from town to have morning cappuccino’s. Must visit the Pomaio winery which is a 10 min drive. Leonardo and Marta were so welcoming and taught us so much about their winery.

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
Christina’s home was beautiful. She was an amazing host, getting us last minute reservations at restaurants and doing a cooking class with us on our last night that was fun and delicious!
Quick stats about villa rentals in Montalcino
Total rentals
100 properties
Nightly prices starting at
G$20,921 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
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Cala Di Forno
- Santa Maria della Scala
- Casa Barthel
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- CavallinoMatto
- Pubblico Palace
- Castiglion del Bosco Winery
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Riva del Marchese
- Cantina Contucci
- Madonna del Latte
- Things to do Montalcino
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