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Villa holiday rentals in Montepulciano

Find and book unique villas on Airbnb

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Popular amenities for Montepulciano villa rentals

Private villa rentals

Top Guest favourite
Villa in Cortona
5 out of 5 average rating, 75 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

CherieRating, 5 stars1 week ago
Immaculate villa with plenty of space for everyone. Exceeded our expectations. Remote location best for people who have a car however peaceful and very close to drive into town in 10 minutes. Amazing restaurants nearby. Spectacular views. Beautiful pool area. Attentive friendly hosts. Especially beautiful Elmo the dog.
Guest favourite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars2 weeks ago
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.
Top Guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 27 reviews

Sestuccina

EmmaRating, 5 stars2 weeks ago
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.
Top Guest favourite
Villa in San Quirico d'Orcia
4.98 out of 5 average rating, 47 reviews

Tuscan villa in the heart of the Val d'Orcia

UlrikeRating, 5 stars3 days ago
I would love to give 6 stars! Tommaso's accommodation is at least as beautiful as in the photos. The house has a wonderful atmosphere and a very pleasant living environment. It is extremely tasteful and cozy and we immediately felt very comfortable there. Everything you need is available and everything was sparkling clean when we arrived. We were particularly pleased with the view from the terrace and from the covered dining area: you are surrounded by an (organic) olive grove and can see over the surrounding valley to the green, rolling hills of Tuscany up to Monte Amiata. On the one hand, there are some very interesting typical Tuscan towns in the area, such as Pienza and Montalcino - we have also "hiked" to these; on the other hand, it is not far to larger cities such as Siena and Montepulciano. A trip to the sea is also easily doable. Tommaso and Laura were always available, helpful and accommodating. We're thrilled!
Top Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars2 weeks ago
We had an amazing stay at the villa. A modern house in a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Guest favourite
Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 64 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

Devon And DavisRating, 5 stars1 day ago
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!
Guest favourite
Villa in Buonconvento
5 out of 5 average rating, 11 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.

Luxury villa rentals

Top Guest favourite
Villa in Poggibonsi
4.93 out of 5 average rating, 45 reviews

Villa with pool in Chianti Area

RickRating, 5 stars1 week ago
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!
Top Guest favourite
Villa in Centro Storico
5 out of 5 average rating, 39 reviews

Charming villa 15' walk to center stunning view

RuthRating, 5 stars1 week ago
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
Guest favourite
Villa in Siena
4.97 out of 5 average rating, 39 reviews

Capanna Di Elfo

MichaelRating, 5 stars3 weeks ago
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.
Guest favourite
Villa in Allerona
5 out of 5 average rating, 34 reviews

Vakantievilla Farmhouse Dolci Hills

JeffRating, 5 stars3 weeks ago
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.
Top Guest favourite
Villa in San Casciano
4.97 out of 5 average rating, 110 reviews

Luxury Villa in the very heart of Chianti

MelissaRating, 5 stars1 month ago
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!
Superhost
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars3 weeks ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
Guest favourite
Villa in Pergine Valdarno
4.95 out of 5 average rating, 87 reviews

La Vignaccia (Farmhouse) - villa w/private pool

DominicRating, 5 stars1 month ago
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.
Top Guest favourite
Villa in Montenero d'Orcia
5 out of 5 average rating, 22 reviews

Tuscany Villa With Pool & Magnificent Garden

GreyRating, 5 stars8 months ago
Barbara’s place was above and beyond our expectations in every way! If you are looking for a place to stay in this general area, don’t hesitate! Barbara was a wonderful host and all the instructions were very clear. The kitchen is very well stocked and we cooked all of our dinners there as we were traveling with a baby. We spent a lot of time hanging out as a family and there was more than enough room for us and both sets of grandparents. The home is very well situated and we loved exploring. There are so many great restaurants in the area. I can’t over state the beauty of the area and the house itself…my family is already dreaming about coming back!

Villa rentals with a pool

Top Guest favourite
Villa in Paciano
5 out of 5 average rating, 6 reviews

Fontanaro/Sangiovese – Pool & Steps to Village

ChristianRating, 5 stars10 months ago
Country slow living at its best combined with outstanding hospitality. Our vacation started right after we entered the apartment which was exactly as described and cleaned to perfection. We immediately got recommendations on possible activities in the region and were actively supported during support with any request we had. We highly recommend this place to anyone looking for some relaxation in a peaceful environment.
Top Guest favourite
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 62 reviews

Beautiful villa with swimming pool in Tuscany

KimberlyRating, 5 stars2 weeks ago
The villa, grounds and hosts were fabulous! The views were amazing, the villa extremely clean and well appointed, the pool absolutely delightful, and the surrounding towns and wineries fantastic to explore. Supermarket very close.
Guest favourite
Villa in Castiglion Fiorentino
4.98 out of 5 average rating, 65 reviews

Tuscany Villa Mammi

ClarissaRating, 5 stars1 week ago
There were 10 of us staying in Simone’s villa and it was such a lovely place to relax. The outside area was huge with many different seating areas. The pool looking over the town below was stunning. Simone was really responsive to any questions we had and gave us suggestions for wine tours and taxis. The indoor kitchen is a little small but still has everything you need. We used the outdoor bbq and pizza oven much more as this was perfect for cooking outside in the sunshine. Thank you for a great stay!
Top Guest favourite
Villa in La Cima
4.94 out of 5 average rating, 31 reviews

- 20% Last Minute 21June-2July Lake View Villa

YedongRating, 5 stars8 months ago
A short while ago, we (4 adults of the same family) stayed in this house. It is located nearby lake Trashmeno and you can have a great view from the house. The traditional house is surrounded with a beautiful garden with a private swimming pool. The house is specious, a big living room and a well equipped kitchen. It is clean. Above all, The hosts Sheetal and Vittorio are super helpful. They waited us at the door steps, gave us all the detailed information about What to do, Where to eat & drink, supermarket, etc. and also helped us to make a restaurant reservation. They responded to our questions throughout with detailed information and links. They are the best hosts to us. Sheetal and Vittorio, many thanks. If we could, we'd like to spend our holiday here again. It is highly recommended.
Top Guest favourite
Villa in Marciano della Chiana
4.95 out of 5 average rating, 77 reviews

La Bacaia

JorgeRating, 5 stars1 week ago
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.
Top Guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 50 reviews

The Lazy Oak

JarrettRating, 5 stars2 weeks ago
There are very few times when a stay not only lives up to expectations, but exceeds them. Our stay at the Lazy Oak did just that. There are no adjectives to truly describe the beauty of the villa and the surrounding countryside. Sitting at the infinity pool, looking out over the olive groves before a dinner prepared in house by a Tuscan chef as the sun sets will go down as one of the greatest days of our lives. We visited the nearby town twice for gelato but the truth is we did not want to leave the property! If you are looking for a peaceful quintessential Tuscan vacation in the countryside, look no further than the Lazy Oak. Mario is on property to tend to any needs but keeps to himself unless called upon. We actually loved his company and called him over to talk on multiple occasions…with the help of Google translation of course. Thank you Mario and Alesandro for an unforgettable stay. We hope to see you again in the future.
Top Guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 74 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

DavidRating, 5 stars1 week ago
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.
Superhost
Villa in Murlo
4.94 out of 5 average rating, 17 reviews

Pompana Rustic Charm Casale

ArtemiyRating, 5 stars3 weeks ago
A great place for a retreat to enjoy the nature and the silence. The Airbnb has a fantastic location in the nature. It has everything that you need for a short an long stay. The view from the balcony is just amazing. Would definitely recommend it!

Quick stats about villa rentals in Montepulciano

  • Total rentals

    10 properties

  • Nightly prices starting at

    $278 AUD before taxes and fees

  • Total number of reviews

    280 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wi-Fi availability

    10 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montepulciano
  6. Villa rentals