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Vacation rentals with a pool in Montepulciano

Find and book unique homes with a pool on Airbnb

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Popular amenities for Montepulciano rentals with a pool

House rentals with a pool

Guest favourite
Home in Civitella in Val di Chiana
4.93 out of 5 average rating, 45 reviews

Casa Fattore - Tuscan countryside house

LunaRating, 5 stars7 months ago
The stay at the Capocontro estate was very satisfying. The entire ancient hamlet is a jewel set in the countryside, with spectacular views of the woods of Val di Chiana. The accommodation is tidy and clean, picturesque and elegantly retro. Piero and Lella were very helpful in communications and suggestions for places to visit and where to eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped for a short time and the weather was a bit capricious, otherwise we would have enjoyed the farm's outdoors more. The only small flaw: the dishes and the fridge were not exactly immaculate, but nothing that can't be solved with a sponge. Super recommended for both a short and a long stay, so you can enjoy the quiet of the place and visit the surrounding area.
Superhost
Home in Florence
5 out of 5 average rating, 5 reviews

New Florence "Afrodite" suite with pool

SarahRating, 5 stars1 week ago
Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!
Superhost
Home in Todi
4.94 out of 5 average rating, 32 reviews

Villa in Umbria with pool

MichaelRating, 5 stars8 months ago
Antonio is a very nice host who always takes care of the house and his guests. The 4 apartments were very good and also convenient for our group vacation. Parking is more than enough on the property as cars are also mandatory to get to the house. Furthermore, the pool is very good and also very large. Enough space to have fun. Antonio came several times to clean the pool, which was very good. Other shade options such as umbrellas or another pavilion would be good, otherwise you have to take them with you beforehand.
Top guest favourite
Home in San Lorenzo
5 out of 5 average rating, 21 reviews

Casa dei Vasi

ChristophRating, 5 stars1 week ago
We were greeted super warmly by Lorenzo's Mama Alba. The apartment even exceeded their pictures. Really very very nice and so comfortable. Has everything you need. Wonderful location and sensational atmosphere. Lorenzo's numerous tips were all gold value and we were able to enjoy Tuscan cuisine every day. The small town of Anghiari is fantastic, a really beautiful place in the middle of Tuscany. Everything worked out great, from the communication with Lorenzo to the " daily care" by Alba. We will miss their loving way. Thanks again all the goodies. This place and accommodation is absolutely recommended and always worth a trip, even for families (rather infants). glg Fam.Fehrmann
Guest favourite
Home in Ficulle
4.96 out of 5 average rating, 23 reviews

Big Breathtaking PoolVilla bw Rm/Fl

PatrickRating, 5 stars8 months ago
Beautiful large house with great views and an amazing pool area. A little remote, at the end of a long and steep gravel road, but completely worthwhile. Great hosts, very attentive to their guests' every need.
Guest favourite
Home in Cortona
4.96 out of 5 average rating, 57 reviews

"Casa Elisa", house with swimming pool at the foot of Cortona

AlessandroRating, 5 stars4 months ago
I had an unforgettable stay at Casa Elisa, located at the foot of beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary amenities. The garden with swimming pool is an oasis of tranquility, ideal for relaxing with a good book or enjoying a sunset aperitif. But it is the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information on places to visit and recommended restaurants makes a difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.
Superhost
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars6 months ago
Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy
Top guest favourite
Home in San Feliciano
4.9 out of 5 average rating, 139 reviews

Casa dei 5 Sensi - Trasimeno view

MichelRating, 5 stars2 months ago
Very pleasant house to stay in, extremely quiet, with superb views of Lake Trasimeno. It is excellently located, since in 30 to 60 minutes by car you can also be in Perugia, Assisi, Arezzo, Siena and so many other beautiful cities. And, for those who prefer to walk or cycle, the lake tour is almost 60 km! Last but not least, Sergio is very friendly, full of attention but at the same time very discreet, and as a man of culture he will give you all the information you would like. For a rental in the heart of Umbria and southern Tuscany, look no further, this is where you want to come. Annette and Michel

Condo rentals with a pool

Superhost
Condo in Loro Ciuffenna
5 out of 5 average rating, 9 reviews

""Beautiful Villa with PRIVATE pool in Tuscany""

BahrinRating, 5 stars15 months ago
Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.
Superhost
Condo in Sovicille
5 out of 5 average rating, 3 reviews

2-bedroom and 2-bathroom apartment, kitchen, pool

MilanRating, 5 stars93 months ago
We received very warm welcome and enjoyed very much Frederica's house, pool, pasta and last but not least Siena , San Galgano and San Gusmo' very much. The place is perfect and I don't remember other spaces from airbnb which can compete with this one. I hope we will be able to come again some time soon.
Superhost
Condo in Pergine Valdarno
4.67 out of 5 average rating, 6 reviews

Relax in farmhouse among the Chianti vineyards

MeganRating, 5 stars7 months ago
Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.
Top guest favourite
Condo in Bibbiena, AR
5 out of 5 average rating, 16 reviews

ideal for two + porch, swimming pool on the farm

ChloéRating, 5 stars8 months ago
We had a great time at this beautiful place. The farm has several apartments, each with their own privacy. The pool was very clean and warm, there was shade available and a shower and toilet right next door. The apartment was as shown in the pictures, there was no air conditioning but it was very cool inside during the day. A few days before our arrival, Isabella sent us all the necessary information and it was her brother Piero who welcomed us very warmly upon arrival. The place was very clean, the kitchen well-equipped and towels were provided. There are many things to do and see in the area, we even had recommendations available. Overall we are really happy and would definitely recommend this place!
Superhost
Condo in Marcialla
4.69 out of 5 average rating, 26 reviews

Csa di Romano – Sunset

RymaRating, 5 stars23 months ago
It was my second time at Il Tramonto (because you will love to come again). It has been a great stay, the perfect spot to visit the Chianti region, as well as rest (garden behind is a bliss) and discover tiny villages around. Laura and Sandra are very welcoming, communication is very easy. I recommend !
Superhost
Condo in Pian di Marte
4.67 out of 5 average rating, 6 reviews

Nerone Apartment

GiuliaRating, 5 stars9 months ago
The accommodation is a small paradise of tranquility. No noise pollution. Wonderful view. Careful environment and a beautiful pool where you can relax and cool off. Antonella and her family are exquisite, kind, and extremely discreet people. strategic location to visit both the villages of Lake Trasimeno and to visit Perugia, Assisi and many other places. The nearby village is enchanting and you can shop for local products. For a more complex shopping just reach the lake village (Passignano) and you can find coop and Conad. the only thing that should be considered is that the area is totally devoid of a mobile network. The house is equipped with wifi, but as soon as you leave the house, even just to go to the pool, you have no way to access the network. For those like us who wanted to disconnect from everything, it was a no problem. If instead you needed to work or be available, it should be considered. overall for us it was a beautiful week of relaxation. It's worth it.
Superhost
Condo in Gavinana
5 out of 5 average rating, 25 reviews

Luxury Views aircon Shared Pool parking cooking

JeevanRating, 5 stars20 months ago
We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!
Superhost
Condo in San Gimignanello
5 out of 5 average rating, 5 reviews

Il Loggiato, 2 bedrooms with a view

LaurenRating, 5 stars7 months ago
Stunning place. Loved the vineyard, olive trees and pool. Exactly what I was looking for in a Tuscan experience!!

Home rentals with a private pool

Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 187 reviews

Stone House with Exclusive Pool Codilungo in Chianti

LeeRating, 5 stars6 months ago
The Stone House was gorgeous - beautifully and thoughtfully decorated, with amazing views. It was private yet easy to get to many amenities/tuscany towns/wineries nearby. Emanuela and Giovanni were very responsive to our questions and requests. We requested for help to buy a bouquet of flowers to surprise our friend for her birthday on the day we arrive - not only did they take the time to help us buy it, they refused to let us pay for it! it was too cold for us to use the pool but I can imagine how wonderful it would have been if we could have used it. all in all, it was a great place to enjoy a dreamy tuscan holiday.
Home in Poggibonsi
4.5 out of 5 average rating, 4 reviews

The Nest by Interhome

MartinRating, 5 stars11 months ago
"The Nest" in the Localitá Torri is a beautiful place. High-quality, absolutely complete and lovingly furnished. Penibel clean. There was nothing missing at all. There is a lot of passion in the apartment. This fits the owner who did the check in and check out himself. Such a pleasant, nice person. An ideal starting point for excursions to the well-known area with San Gimignano, Volterra, Siena, Florence, etc. Absolutely recommended
Top guest favourite
Home in Pergaccio
5 out of 5 average rating, 46 reviews

Villa Pergo is an ancient charming country villa

TerriRating, 5 stars6 months ago
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi
Top guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 223 reviews

Explore nature in the center of Vigneti Chianti

ElinRating, 5 stars3 weeks ago
Beautiful place with amazing views! 100% recommend to stay at Rita’s place, definitely recommend!
Top guest favourite
Home in San Casciano In Val di Pesa
5 out of 5 average rating, 42 reviews

Charming villa in the Chianti hills

Kihun (KI)Rating, 5 stars4 days ago
The place we stayed this time was really artistic and beautiful. Thoughtfully arranged objects and unique touches throughout the space made me feel like I was in a small gallery. The colors combined with the natural light coming in through the window, and the quiet and cozy atmosphere — I was satisfied without missing anything. In particular, I was impressed by the details filled with the unique sensibility of the accommodation, so I felt special every moment throughout my stay. It is a place I would definitely recommend to those who want to get away from daily life and heal in an artistic atmosphere.
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
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!!
Guest favourite
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 92 reviews

Casa Luigi Suite with exclusive pool

DanielleRating, 5 stars7 months ago
Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!
Guest favourite
Home in Castiglione del Lago
5 out of 5 average rating, 25 reviews

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool

ChristopherRating, 5 stars6 months ago
We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!

Quick stats about vacation rentals with a pool in Montepulciano

  • Total rentals

    20 properties

  • Nightly prices starting at

    $125 CAD before taxes and fees

  • Total number of reviews

    520 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Wifi availability

    20 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montepulciano
  6. Rentals with pools