
Holiday rentals with a pool in Montepulciano
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Top-rated rentals with a pool in Montepulciano
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House rentals with a pool

Casa Fattore - Tuscan countryside house
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.

New Florence "Afrodite" suite with pool
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!

Villa in Umbria with pool
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.

Casa dei Vasi
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

Big Breathtaking PoolVilla bw Rm/Fl
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.

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

Beautifully restored villa with private pool
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

Casa dei 5 Sensi - Trasimeno view
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
Apartment rentals with a pool

""Beautiful Villa with PRIVATE pool in Tuscany""
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.

Casa Eva, near Orvieto, amazing views + pool
This was a beautiful country side house amidst olive gardens. It was clean, well furnished and convenient. Tony and Joanne went above and beyond to make us feel at home. Would stay here again in a heart beat if I’m in the area!

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

Relax in farmhouse among the Chianti vineyards
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.

ideal for two + porch, swimming pool on the farm
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!

Three-room apartment with 2 bedrooms and private garden, swimming pool
Wonderful place, very nice host. Thank you for your hospitality, Silvia

Luxury Views aircon Shared Pool parking cooking
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!

lovely farm- apartment (Fox)
My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.
Home rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
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.

Villa Pergo is an ancient charming country villa
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

Explore nature in the center of Vigneti Chianti
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.

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!

Charming villa in the Chianti hills
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.

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!!

Casa Luigi Suite with exclusive pool
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 !!
Wp Relais Villa Vignalunga
Had the most amazing time in this beautiful place! Stayed for 5 nights, two families with young children, and felt at home once we got there. We were amazed by the design and surroundings. Not enough words to describe!
Quick stats about holiday rentals with a pool in Montepulciano
Total rentals
20 properties
Nightly prices starting at
£68 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
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- Marina di Grosseto beach
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Kite Beach Fiumara
- Terme Dei Papi
- Basilica of St Francis
- Podere La Marronaia, Sosta alle Colonne
- Tenuta Le Velette
- Cantina Colle Ciocco
- Cantina Stefanoni
- Mount Subasio
- Cala Di Forno
- Cantina de' Ricci
- Madonna del Latte
- Casa Del Cioccolato Perugina
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Podere Il Cocco
- Ugolino Golf Club
- Pubblico Palace
- Castiglion del Bosco Winery
- Cantina Contucci
- Golf Club Toscana