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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 favorite
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 satisfactory. The entire old village is a jewel set in the greenery, with spectacular views of the woods of the Val di Chiana. The place is tidy and clean, picturesque and elegantly retro. Piero and Lella are very available in communications and suggestions of places to visit and eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped little and the weather was a little capricious, otherwise we would have enjoyed the exteriors of the farm more. Only small mole: the dishes and the fridge were not really immaculate, but nothing that can't be resolved with a sponge shot. Highly recommended for both a short and long stay, so you can enjoy the quiet of the place and visit the surroundings.
Guest favorite
A private jacuzzi is featured in a cozy outdoor space, surrounded by wooden beams and landscaped greenery. Soft lighting enhances the serene atmosphere, inviting relaxation after a day of exploration. Steps lead up to the jacuzzi, providing easy access.
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
A spacious outdoor area features a large swimming pool surrounded by well-maintained grass. The pool area includes several white lounge chairs and is complemented by a nearby shaded seating space. Rustic stone buildings are visible in the background, amidst lush greenery.
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 favorite
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 favorite
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 favorite
A private pool area is framed by lush greenery and blooming flowers. Two lounge chairs and a small table are arranged on a stone patio under a large umbrella. The bright yellow house is partially visible, showcasing an upper balcony.
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 the 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 comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.
Superhost
A private pool is situated within a spacious, well-kept lawn, surrounded by tall trees and lush greenery. Lounging chairs are placed beside the pool, providing a comfortable spot for relaxation. Clear blue skies create a serene atmosphere, enhancing the tranquil outdoor setting.
Home in Cortona
4.92 out of 5 average rating, 26 reviews

Beautifully restored villa with private pool

RoxarnaRating, 5 stars7 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 favorite
A private swimming pool is framed by landscaped greenery, with steps leading into the clear water. The expansive water surface reflects the distant view of Lake Trasimeno and the surrounding landscape under a partly cloudy sky.
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
A private swimming pool is surrounded by lounge chairs and umbrellas, inviting relaxation. A hammock offers a serene spot to unwind. Lush greenery frames the pool area, and the apartment structure is visible in the background, blending with the natural landscape.
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.
Top guest favorite
A shaded pergola supports climbing greenery, providing a serene view of the salt-water pool surrounded by lounge chairs. Stone walls and lush greenery create a tranquil setting under a clear blue sky.
Condo in Orvieto
4.97 out of 5 average rating, 37 reviews

Casa Eva, near Orvieto, amazing views + pool

RajeshRating, 5 stars1 week ago
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!
Superhost
A serene pool area is presented, featuring a clear water swimming pool surrounded by lush greenery. Ambient lighting highlights the space, creating a peaceful atmosphere. Tables and chairs are arranged nearby, inviting guests to relax and enjoy the outdoor setting during the evening.
Condo in Sovicille
5 out of 5 average rating, 3 reviews

Apartment with 2 bedrooms and 2 bathrooms, kitchen, swimming 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
A two-level swimming pool is set amidst landscaped greenery, featuring a shallow area leading to deeper sections. Loungers are arranged in a sunbathing area surrounded by olive trees, while a rustic building is visible in the background, providing a scenic backdrop.
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 favorite
An aerial view highlights a spacious homestead surrounded by lush green fields and well-maintained gardens. The landscape features a combination of agricultural land and residential areas, with a road creating a natural separation between them. Trees provide a soft border to the property.
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!
Guest favorite
Condo in Volterra
4.95 out of 5 average rating, 21 reviews

Three-room apartment with 2 bedrooms and private garden, swimming pool

JanRating, 5 stars9 months ago
Wonderful place, very nice host. Thank you for your hospitality, Silvia
Superhost
A shared swimming pool is set within a serene garden, surrounded by olive trees. Comfortable lounge chairs are arranged around the pool, complemented by a neat patio area. The clear water reflects the sunlight, enhancing the inviting atmosphere of the outdoor space.
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!
Guest favorite
A spacious swimming pool is surrounded by manicured grass and framed by tall trees. Sun loungers are arranged on one side, and umbrellas provide shade, creating a relaxing outdoor space. A clear blue sky with scattered clouds adds to the serene atmosphere.
Condo in San Casciano In Val di Pesa
4.83 out of 5 average rating, 215 reviews

lovely farm- apartment (Fox)

DavidRating, 5 stars6 months ago
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

Guest favorite
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.
Top guest favorite
An aerial view showcases the expansive grounds of Villa Pergo, surrounded by lush greenery and fields. The infinity pool is highlighted, surrounded by sunbeds and shaded by cypress and ancient trees. The countryside landscape stretches into the distance, enhancing the villa's serene setting.
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 favorite
A shared infinity pool is surrounded by tall cypress trees, providing a tranquil atmosphere. Comfortable lounge chairs set along the poolside invite relaxation under the shade of a large umbrella. The lush greenery and rustic building in the background complement the serene setting.
Farm stay in Arezzo
4.97 out of 5 average rating, 224 reviews

Explore nature in the center of Vigneti Chianti

CameronRating, 5 starstoday
We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.
Top guest favorite
The villa is surrounded by lush greenery and tall trees, providing shade to a spacious outdoor seating area with a pergola. Steps lead up to the entrance, framed by well-manicured hedges, while a stone barbecue area is positioned nearby.
Villa in San Miniato
4.88 out of 5 average rating, 40 reviews

Historic home with exclusive pool

AylaRating, 5 stars9 months ago
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!
Top guest favorite
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 stars5 days ago
The place I stayed at this time was really artistic and beautiful. Thanks to the carefully placed objects and the unique interior, I felt like I was staying in a small gallery. From the natural light coming in through the window, to the colors that go well with it, to the quiet and cozy atmosphere — I was satisfied with everything. In particular, the details filled with the sensibility of the accommodation were impressive, so every moment felt special throughout my stay. This is a place I'd like to recommend to those who want to escape from everyday life and heal in an artistic atmosphere.
Guest favorite
A spacious room features polished black and white marble flooring, with large arched windows allowing natural light to fill the space. A glass-top table is elegantly set with decorative glassware, while a cozy seating area with a light-colored couch complements the tranquil ambiance.
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 favorite
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 favorite
A rustic stone villa is set against a backdrop of rolling hills, showcasing the charm of Tuscany. A large, organically shaped swimming pool is visible in the foreground, accompanied by well-maintained gardens surrounding the property.
Villa in Castiglione d'Orcia
4.96 out of 5 average rating, 94 reviews

Wp Relais Villa Vignalunga

Hila & DeanRating, 5 stars1 week ago
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 vacation rentals with a pool in Montepulciano

  • Total rentals

    20 properties

  • Nightly prices starting at

    $90 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