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House vacation rentals in Montepulciano

Find and book unique houses on Airbnb

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Popular amenities for Montepulciano house rentals

House rentals with a pool

Top guest favorite
Home in Castiglion Fiorentino
5 out of 5 average rating, 36 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars1 month ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Top guest favorite
Home in Barberino Tavarnelle
5 out of 5 average rating, 108 reviews

Infinity pool in Chianti area

KrisRating, 5 stars2 weeks ago
"Perfect" is the only word that comes to mind for Anna's place. Such a serene location and perfect for a family. The view is just spectacular. We felt so at home and loved sitting out in the yard and by the pool. Anna provided us with a list of so many amazing things to do/see near and far. A must do is the pasta making with Vilma at the house-the most memorable and delicious meal from our trip! Can't wait to go back there to live more of the Tuscan life and enjoy the most beautiful view. Thank you, Anna, for hosting such a gem!
Guest favorite
Home in Arezzo
4.9 out of 5 average rating, 166 reviews

Italian Interior

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Guest favorite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Guest favorite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars3 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Guest favorite
Home in San Martino
4.94 out of 5 average rating, 212 reviews

Casa Bada - Barn

RaymondRating, 5 stars3 weeks ago
Great place and location. everything about the place and our stay was excellent.
Guest favorite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 108 reviews

The Owl: view, pool and garden

JasonRating, 5 stars4 weeks ago
What a great place to stay while visiting Tuscany. The home is a renovated medieval watchtower located up a dirt road, tucked on a hilltop overlooking the valley. Jacopo, the host, was so kind, hospitable and responsive during our 5-day visit. Would definitely recommend this place to explore Tuscana.

House rentals with free parking

Guest favorite
Home in Castelmuzio
4.93 out of 5 average rating, 42 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars3 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favorite
Home in Asciano
4.94 out of 5 average rating, 35 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars2 weeks ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Top guest favorite
Home in Montebenichi
5 out of 5 average rating, 59 reviews

[Little Escape] 4 Beds + Private Panoramic Pool

SusanRating, 5 stars3 weeks ago
Our stay in Montebenichi was almost indescribable. Having been to Tuscany before, this time was pure magic. The flat is within the compound of a 12th century fortress village that is mostly inhabited by residents. Tommaso had stocked the kitchen with plenty of coffee, milk, water, juices, snacks and his grandmother's amazing Limoncello! The pool area has the most incredible view with an outdoor kitchen where Tommaso arranged for us to have a traditional Tuscan cooking class. He also made reservations for us at the village Michelin-rated restaurant that is just steps from the flat. One of our favorite things was hearing the wolves of Tuscany howl in the distance - no need to be afraid - it was pure magic. We saw very few tourists which made the experience even better. Moreover, Tommaso was THE BEST HOST we have ever had while staying at an Airbnb. His dedication to ensuring the perfect stay for us was truly a standout. We can not say enough good things about our stay!
Top guest favorite
Home in Perugia
4.98 out of 5 average rating, 124 reviews

La Perla del Lago Holiday home

KaseyRating, 5 stars3 days ago
We cannot express how much we loved our stay at Saverio’s. It was absolutely PERFECT! From the moment we arrived, we felt completely at home. The home itself was beautiful in construction, clean, stylishly decorated, and thoughtfully stocked with everything we needed, including little extras like fresh coffee, teas, local advertisements for restaurants, and also recommended the local grocery for toiletries or food items. Saverio’s home couldn’t be in a better location, tucked in a charming part of the countryside with views that will take your breath away and make you fall in love with this part of Italy. Even being out-of-town, you are close to everything. The town of Magione has a wonderful and friendly restaurant with fantastic pizza and entrees- I Cento Passi. Saverio, thank you for allowing us to stay in your beautiful home, we are grateful for the experience.
Top guest favorite
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars1 month ago
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
Superhost
Home in Lucignano
4.83 out of 5 average rating, 41 reviews

La Casetta

JonasRating, 5 stars2 weeks ago
Hard to find a place like Maria’s, beautiful place and with such a friendly and helpful staff.
Superhost
Home in Monteroni d'Arbia
4.88 out of 5 average rating, 192 reviews

The Tower of Corsanello

RobRating, 5 stars2 weeks ago
We loved our stay here. It is a beautiful home and a beautiful space. The only thing I would note for future travelers is the host speaks Italian and not much English. Communication prior to check-in was a little slow but ultimately very smooth. The host met us when we arrived and was very nice. Would 100% stay here again.
Guest favorite
Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 89 reviews

The Chianti window

KirstenRating, 5 stars2 weeks ago
This beautiful Tuscan home stole our hearts and we will definitely be back to enjoy this peaceful, spacious and authentic home. Sarah and her family were incredible hosts and made us feel right at home. We are absolutely in love with our experience here and would highly recommend the stay!

Weekly house rentals

Top guest favorite
Home in Loc. Casalini - Comune Panicale
4.99 out of 5 average rating, 95 reviews

Cottage surrounded by nature

AlanRating, 5 stars1 week ago
Stayed here last week for 5 days. On arrival we were met with a welcome basket of food a bottle of wine a bottle of homemade olive oil and also bottles of water on arrival. The pictures don’t do it justice it felt like a place out of a fairytale, the property is surrounded by tons of olive trees and greenery. If you want a quiet relaxing holiday this is place to go. Rosella was amazing with quick responses and extremely welcoming, we are definitely going again next year.
Top guest favorite
Home in Monticchiello
5 out of 5 average rating, 41 reviews

Lovely home to dream

CadeRating, 5 stars1 week ago
This place is definitely a piece of Tuscany Italy. it will always hold a special place in my wife's and my heart with how beautiful and amazing the house was and the town it is located in. it seemed very well located, close to hot springs, multiple other cities, beautiful country side with horse back riding, world class winery's, ect. She is a great host and I would highly recommend this Airbnb to anybody looking for a one of a kind experience in Italy.
Top guest favorite
Home in Montepulciano
5 out of 5 average rating, 22 reviews

Casa di Mela

BeritRating, 5 stars1 week ago
We loved our visit at the accommodation! Beautiful city, lovely flat, great area. Very clean and nice to live in, the benches in front are perfect for concluding the evening with a glass of vino nobile di montepulciano. Modern stove and kitchen allow for easy cooking, always a blast. 5/5.0
Top guest favorite
Home in Montevarchi
5 out of 5 average rating, 25 reviews

Casa San Ripa: Relax Oasis with Private Pool

CarolinaRating, 5 stars4 days ago
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!
Top guest favorite
Home in Magione
5 out of 5 average rating, 20 reviews

Beach House, on the shores of Lake Trasimeno

Juan DiegoRating, 5 stars2 weeks ago
To value this property, you have to start with the HOST, a professional in every sense. From the minute 0 of the reservation, until check-out; always attentive, very friendly and very professional. It's a pleasure to meet serious people and this gives the app value. The beach house is a paradise in Italy. Easy access, attention to detail, peace, nature, comfort. Our trip was as a family with our two poodles and I think they were the ones who enjoyed the property the most, seeing them run and jump through the green areas of the property and live with many birds, rabbits is priceless. Our daughter enjoyed her stay studying and with the peace and quiet of the place, it was easy for her to concentrate. We, on the other hand, did some sightseeing in the area, everything is very close and well connected by road. It is a very well-kept, safe property and above all, enjoying its sunset, sitting on a lounger, enjoying a good wine (from the area) is an unrepeatable experience. Thank you Maurizio.
Top guest favorite
Home in Montepulciano
4.95 out of 5 average rating, 21 reviews

Hortus Conclusus House

MichelleRating, 5 stars1 week ago
Apartment was centrally located in the town. Very walkable to shops and restaurants. Beautiful sunrises through bedroom window. Very responsive hosts, especially with getting to the apartment from the train station (no Uber or taxi services when we arrived, so my advice is to get off at the previous stop if coming from Florence or make advance taxi arrangements). The hosts were very helpful and called their go-to cab driver. Beautiful with town and can’t wait to return!
Guest favorite
Home in Montepulciano
4.85 out of 5 average rating, 33 reviews

Stunning Tuscany Villa in Montepulciano

LaurenRating, 5 stars2 weeks ago
We had a wonderful stay! The location was perfect. We especially enjoyed the flexibility to use the kitchen for cooking after much eating out and lived mornings and evenings on the roof top terrace!
Superhost
Home in Montepulciano
4.86 out of 5 average rating, 50 reviews

the birds view

AntonRating, 5 stars2 weeks ago
The apartment was in a great location. Sunsets have been etched in the retina forever :) What a great view! Easy walking distance to all restaurants and other attractions in Montepulciano.

Quick stats about house rentals in Montepulciano

  • Total rentals

    50 properties

  • Nightly prices starting at

    G$10,460 GYD before taxes and fees

  • Total number of reviews

    2.1K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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