
Vacation 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

Italian Interior
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!

Family Forest - Pool in the Crete Senesi
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings are beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here

Vineyards Paradise
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!

Charming estate with views
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.

Antico Borgo Ripostena – n. 8 Old House
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

Nada Home
We had the best week in Nada’s home with our friends who travelled from Australia. The villa was so cute and cosy and had everything you would need. Nada is a great host who was very responsive and extremely friendly, it was just a shame we didn’t get to meet her in person. The main highlight for us was when Viola (Nada’s daughter) came to the villa and did a cooking class with us. It was fantastic and one not to be missed! We made bruschetta, homemade pasta and sauce and a lemon tiramisu. We made pasta and bruschetta literally every night after as it was just so good. From the villa we travelled around in our hire cars and saw the delightful towns/villages such as San Giginano, Certaldo, Siena, Greve in Chianti, climbed up the hill to Montefioralle, Radda in Chianti, Volpaia and the local village of Barberino Val D’Elsa. I highly recommend you visit each as all close enough for a day out it combine a couple in a day. You will not be disappointed at Casa Di Nada. We loved it 😊

Gaiole in Chianti Poggio Casabianca
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!

House Rigomagno Siena
A fantastic place to stay! Diego is extremely welcoming and gave us great recommendations and local info. The house and garden are even more beautiful than the photos - everything well-equipped, all that we needed. We had the perfect, peaceful week and look forward to coming back!
Condo rentals with a pool

Chianti La Pruneta, Michelangelo apartment.
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.

Loggiato 3 apartment in Tuscany near Siena
We had a great stay in Francesca's agriturismo. beautiful place with breath taking views. the place was very clean and tidy and it had all we needed and much more. it was a good base for traveling the area. take a ride on the SP146 - you won't regret it! all in all this place is highly recommended! wish i would visit here again. Toscany is soo beautiful.

La Foresteria | Granary House
This place is even more beautiful than the photos show! We are travelling round Italy for our honeymoon and this has been our highlight. From the amazing grounds to the incredible food at the little restaurant it’s all been perfect. Thank you Marian for excellent communication and being so accommodating. What a fantastic place - Grazie!!

Adalberto Apartment inside the Manor of Fulignano
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

Casa Rebecca with a small private pool
Benedetta is an amazing and gracious host, the property was easy to locate and the room was beautiful, absolutely amazing Tuscan style with beautiful views and a private pool. She also recommended us a restaurant for dinner and that was one of the beat meals we had in Italy! 100% recommend

VILLA LE PERGOLE - Florence
Anna was a fantastic host, who treated us with the upmost respect and kindness. While her place is a bit difficult to find at first, once you're there, you're in one of the most beautiful scenes we've seen during our time in Italy. Also, it was close enough that we were still early able to travel into Florence each day we were there. Anna was so nice in providing us with breakfast each morning, which included apricot jam from her fruit trees and homemade bread. We would recommend this spot for anyone looking for a quiet place to stay outside of the busy city.

House between Firenze, Arezzo, chianti e Siena
We immediately fell in love with this property. Everything here makes up the image that can be made of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!

Agriturismo Casavecchia, l'Olivo
We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.
Home rentals with a private pool

Tuscan Villa Featured Conde Nast Best Villas Italy
This 500 year old house is ideally situated in Tuscany and the Chianti region. It is a perfect place for day trips to other towns, for wine, tasting excursions, and for visiting Florence. The idyllic setting gives you a sense of country life in Italy, and the views from the patio and house are stunning. There are spectacular wineries within 5 to 10 minutes of the house. We found the house very comfortable and enjoyed our stay very very much. Rose and Pier couldn’t have been more helpful in planning our stay and excursions. We found through them fabulous restaurants, and wineries that we would not have discovered on our own. They were also incredibly responsive when we had questions. Our only confusion about the house was that the listing showed three bathrooms, but one was in the laundry room in a separate building . Just something to know. Thank you to Rose for a lovely vacation ! It was the perfect place to explore Tuscany from!

Stone House with Exclusive Pool Codilungo in Chianti
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Historic home with exclusive pool
We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. There is plenty of parking. Only the potholes and the access to the villa are a bit challenging - but doable!

Angeli by Interhome
We are one big family (15 people- adults and children). We booked the villa for 1 week and we had a wonderful time. The inside is beautiful, very spacious and well maintained. The kitchen is well equipped and there is a big dinning table enough for everybody to seat at. There is a big living room, TV room and a decorated library. The rooms are also spacious and each one has its own bathroom. One negative is that the villa doesn't have air condition. However, when we stayed the weather was chilly and there was no need for cooling/heating. The garden is massive. There is a big swimming pool with furniture to relax around it. Although the water was still very cold, the children did not skip the fun of swimming. There is outdoor cooking area near the pool with a big grill. We used it few times to barbiqu. There was also enough space for us to park 4 cars. The hostess and the owner were great. We received a quick response to any question or request. This villa is a great choice. ⭐️⭐️⭐️⭐️

Charming villa in the Chianti hills
We stayed in the villa for 3 weeks with my family (2 young kids) and it was absolutely perfect!!! Francesca was an incredible host, fantastic communication. The house itself was beautiful, clean and the pool was just magic. Close to Florence and all the wonderful towns nearby, we can’t recommend this place enough. Would stay again without hesitation.

Podere Molinaccio - Luxury Tuscan-style Eco Villa
Absolutely amazing stay at this villa. Pool was perfect, villa was stunning, AC was much appreciated in the 90 degree heat, and the host was one of the very best ever! She was as our personal concierge helping set up a private chef, olive oil and wine tasting, truffle hunting and more. We spent a week and could have stayed longer there is so much to explore in Umbria and Tuscany and we absolutely loved it!

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
I looked at dozens of other ABBs before choosing Giovanna's place and I know I made the best choice after staying. The setting is absolutely beautiful and peaceful. Lounging at the pool was so nice. We had the pool all to ourselves which is hard to find with other ABBs. The home is a nice large space and very clean. The views out the window are great. Giovanna was so nice and welcoming just a wonderful person. We enjoyed having a drink with her and Luigi. I highly recommend her place.
Quick stats about vacation rentals with a pool in Montepulciano
Total rentals
20 properties
Nightly prices starting at
G$18,819 GYD 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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- Lake Trasimeno
- Lake Bolsena
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Tenuta Le Velette
- Santa Maria della Scala
- Terme Dei Papi
- Cantina Stefanoni
- Basilica of St Francis
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Cantina Colle Ciocco
- Castiglion del Bosco Winery
- Pubblico Palace
- Mount Subasio
- Golf Club Toscana
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Cantina Contucci
- Podere Il Cocco
- Madonna del Latte
- Abbey of Monte Oliveto Maggiore