
Villa vacation rentals in Montepulciano
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Top-rated villa rentals in Montepulciano
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 Montepulciano villa rentals
Private villa rentals

Villa Comunaglia - Design Villa with Private Pool
Andrea is a great host. The stay was amaizing and the support received from Andrea during stay was priceless. The place is wonderfull with great view and outstanding privacy. I will recommend Andrea as a host and his place as great choice for holidays.

Villa La Cingallegra
Fantastic all around experience. Thank you Elio and team 🙏🙏

Villa Febea - Villa Febea 16
Nestled in a stunning landscape, the villa is a marvelous retreat that captivates with its beauty and generous space. Meticulously maintained to uphold high standards, the villa's kitchen is thoughtfully equipped with all the essentials for a comfortable stay. Furthermore, each room is fitted with its own shower and toilet, ensuring privacy and convenience for all guests. The pool adds an extra touch of wonder to the experience. As for the hosts, Alice and Jacopo, they are simply delightful, providing warm hospitality throughout your stay. I wholeheartedly recommend this exceptional villa for an unforgettable getaway

Villa il Palagio in the Tuscan countryside
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!

Villa "La Civetta" with swimming pool, sauna and jacuzzi
Lovely modern home in a beautiful, quiet town in southern Tuscany. We had a wonderful 8 days there with our 6 year old son.

Villa near Florence: Pool, AC, Vast natural garden
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.

Villa with great view over Florence, pool, Wi-Fi
Great place, responsive host. Will be back.
Luxury villa rentals

The House of the Sole del Sodo
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!

Spectacular villa with a view and infinity pool
Superb villa for 12 guests. 10 mns drive to a fabulous town or stay at home in comfort including an excellent pool surrounded by Impressionist views. Teresa is a gem. Pia recommended Eugenio and Pasquale of Italian Show Cooking and they produced a magnificent eight course banquet for my wife's 70th birthday party. This villa holds a very special place in our hearts and the hearts of our guests. Cman you give more than five stars?

villa "La Fonticina"
This house is a jewel and I feel so lucky Cesare shared it with us. Highly recommend to anyone looking for a comfortable and beautiful place!

Villa San Lorenzo | Private Pool, AC & Jacuzzi
The house was great with amazing countryside views. The rooms and common areas were spacious. Our favorite spot was the enclosed patio dining area where we had breakfast every morning overlooking the rolling hills. The hosts were great, very responsive and helpful.. One of the hairdryers was not working but Maurizio got us 2 new ones in no time. He also gave us recommendations for restaurants. Awesome hosts!
Historic home with exclusive pool
We (7 friends) enjoyed staying at the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She sent us a lot of tips about the area (including the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed something, an answer came very quickly. The villa is well equipped and the surroundings are beautiful. There is plenty of parking space. Only the potholes and the access to the villa are a bit challenging - but doable!

Villa Lualdi
Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.

TUSCANY FOREVER PRIVATE VILLA TEMPO
The villa was just gorgeous and the rolling hills from any direction delivered a beautiful Tuscan experience. We arrived late at night and did not expect a rocky 2 km driveway-just a heads up to others.

Villa L 'elsa
The house is amazing and the exterior is beautiful
Villa rentals with a pool

Charming villa on two levels - Casa Lola
Mel is a fantastic host and the place is exactly like in your most vivid Tuscany dreams.:) It's not our first time here and we absolutely loved everything about the place. We booked all three homes available at Mel's place and had an unforgettable week with the entire family - highly highly recommended! Thank you, Mel for being absolutely fabulous!✨

Villa Angiolina
Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!

Villa in Montepulciano with a Pool
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

Poggio degli Ulivi, charming Chianti with pool
The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.

Private Villa with swimming pool in Tuscany
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Elisa Villa
Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.

Villa Casa al Povero
I don’t even know where to begin describing this place. It was the most amazing place I have ever stayed. If you are looking for a peaceful and private villa with incredible views, then stop looking. This is it !! All of the reviews we read before we arrived talked about how amazing the views are and that you must take up the offer if Paola and Alessandro offer to cook a meal for you. Both recommendations are spot on. The sliced beef was one of the best meals I have ever had, and I often found myself wandering around outside the villa looking at the 360 degree views in all directions. We all felt so sad to leave this magic place. Paola and Alessandro were perfect hosts. Always friendly and with a smile on their faces. It’s a long way from Australia but I really hope we get an opportunity one day to return to this majestic place.

Private Villa with semi-Olympic pool and Tennis
Francesca’s home was beautiful and in a breathtaking, peaceful location. There is a short, beautiful walk with Mountain View’s and olive groves to an incredible pool and pool house. She was incredibly helpful in helping us not only access the home, but also in providing us local recommendations. The meal that Ettore prepared for us was one of the highlights of our trip.
Quick stats about villa rentals in Montepulciano
Total rentals
10 properties
Nightly prices starting at
$250 CAD before taxes and fees
Total number of reviews
280 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Marina di Grosseto beach
- Kite Beach Fiumara
- Santa Maria della Scala
- Tenuta Le Velette
- Avignonesi Winery Fattoria Le Capezzine
- Podere La Marronaia, Sosta alle Colonne
- Cantina Colle Ciocco
- Mount Subasio
- Cantina de' Ricci
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Madonna del Latte
- Cantina Stefanoni
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Cala Di Forno
- Pubblico Palace
- Golf Club Toscana
- Cantina Contucci
- Podere Il Cocco
- Castiglion del Bosco Winery
- Ugolino Golf Club