
Condo vacation rentals in Montepulciano
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Top-rated condo rentals in Montepulciano
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Popular amenities for Montepulciano condo rentals
Weekly condo rentals

Milipano Studio Apt
We really enjoyed this place. It exceeded our expectations. It was close to the old town. Pros Shower was excellent. It had Kleenex which was unusual in Italy. It was efficient use of space. Towels/bath sheets were very soft and nice. For an efficiency it had plenty of room for two. Bed was very comfortable. Cons It did not have a comforter..only a blanket. It is close to restaurants and had issue with flies. (Need a fly swatter). Parking—it is VERY limited and plan on paying for it.

Simple and spacious apartment in Palazzo Bucelli
I stayed at Palazzo Bucelli in Montepulciano from May 17 to May 31, 2025, and it was a wonderful experience. The apartment is exactly as advertised—beautiful, plenty of space, and exceptionally quiet. Vania is an amazing host: kind, helpful, and attentive. She even saved a parking space for me, which made arrival and unloading very easy. The location is perfect—just steps away from dozens of restaurants and within easy walking distance to a well-stocked supermarket. The kitchen is fully equipped with everything you might need for cooking. One of my favorite parts of the stay was watching hundreds of swallows dancing in the sky every morning and evening, right outside the dining room window. It was magical. I highly recommend this apartment and would love to return someday.

Casa degli Allegri
My stay at Antonio's Airbnb was an absolute dream, largely thanks to their incredible hospitality and super communicative nature. From the moment I booked, he was on top of everything, providing clear instructions and quickly answering any questions I had. But what truly set this experience apart were the thoughtful, personal touches. The curated playlist waiting for me was the perfect soundtrack to my trip, and their insider recommendations on local hotspots led me to some truly hidden gems I would never have discovered otherwise. It felt less like a rental and more like visiting a friend who genuinely wanted me to have the best time in Florence. I highly recommend Antonio's place for anyone looking for a seamless, enriching, and truly memorable stay!

Santa Cruz Air - Historic Apartment
A great experience overall: easy access to all attractions meanwhile far away enough from the over-crowded city center. Luca is super helpful, he gave clear instructions, offered to help arrange taxis, and suggested really great spots to visit and dine. The apartment itself is as described and large enough for two. The only thing to notice is that it’s on the second floor with narrow stairs.

Spinosa Apartment in Podere Capraia
We had a wonderful time at Alberto‘s and Laura‘s - it turned out that we didn’t do as many trips into the surroundings as planned because we just wanted to enjoy the beauty of the garden and the amazing views. It was the perfect ending of a fantastic vacation in Italy - I hope we will be back next year :) We received a fantastic welcome, home made bread, jam and pasta - and immediately felt like home. Grazie! One thing to mention is that the apartment is kind of thin-walled towards the second apartment - that didn’t bother us at all, but might be of interest for fellow travellers who are sensitive to noises. All in all, certainly one of the best accommodations we have stayed in!

La Foresteria | Betto House
An amazing super-authentic place in the middle of the Tuscan nature & fields ! The hacienda style accommodation truly offers a unique experience of the Tuscan country side. The accommodation is very authentic while also offering on-site restaurant with excellent food and excellent wine. The hosts are truly amazing and will go the extra mile to make your stay unique. The location is also very good as it is easily connected with main points of interest (i.e. places to visit, eat, etc).

a.d. 1237
What an incredible stay!! 10/10. We traveled all over Tuscany for 2 weeks and this stay ranks right up there at the top. From the communication and ease of getting to the apartment to the beautiful old history of the building and town. Just wow! Book it:) We loved the town and her people🫶🏼 The apartment was comfortable in every way. Grazie mille, Heather & Beth

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
Pet-friendly condo rentals

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.

Central apartment overlooking Santa Maria Novella.
We enjoyed the stay at Claudio’s place , the apartment is conveniently located . Claudio was waiting for us at the apartment to greet us and to shows the functionality of all amenities , we found the apartment nicely decorated and squeakily clean . We highly recommend this place for a family of 3 or 4 traveling to Florence . We will be back .

Dafne's House - Cozy & Lovely Apartment
Aida's place was wonderful! We loved everything about it. It's very spacious and decorated beautifully. The air-conditioning was fantastic to come home to after long days sightseeing in very warm weather. We highly recommend Aida's place for a "home away from home."

Elegant vintage decorated home in the old Siena
Perfectly located vintage decorated home within walking distance of historic center of Siena. We spent a month here and used her place as a center base to discover Tuscany. Close to shopping and restaurants. WiFi is excellent as my husband worked remotely for a few days a week. Kitchenette and washing machine were a big help as we cooked a few nights staying in. Mattress is very comfy and the apartment is very quiet. Church bells rang daily and drummers in the contrade practice for parades and Palio. Experience Medieval Siena here. We were very comfortable in Grazia’s place. Nice to have a 1/2 bath on main level, as bedroom and bathroom with shower is on the upper level. Grazia provides everything you could possibly want and has excellent suggestions for places to eat and sights to visit. She was indispensable helping us always responding within minutes if we had a question or needed help. Perfect place for the Tuscan vacation! Grazia is a wonderful and caring host!

Stylish Terrace on Boboli Gardens
We loved this space and when we come to Florence again we will most definitely book here. It was a cool, quiet oasis on the beautiful relaxing side of the Arno. The location was perfect with an easy walk to all the sites but also so quiet and peaceful. We loved the kitchen and cooked multiple days and sat on the sweet patio and enjoyed the local wine. The space was clean and cool and the layout was perfect for 2 people. There’s also a couch bed if another person or one or two children were there. Our hosts were so accommodating and friendly! We have so much love for this special spot in Florence.

Designer Apartment with Breathtaking Views
I enjoyed my stay at Dan's apartment. It was large (even more so when you factor in the adjacent terrace), beautifully furnished and well stocked. Appreciated the dishwasher and clothes washer. Having a second bathroom was an extra perk. Only slight downside was the walk into the center of town (25 min to the Ufizzi) as it rained nearly every day during my weeklong stay -- I imagine on dry/temperate days it's a pleasant walk along the river. Overall I would gladly stay again.

Il Vecchio Noce
A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise doable if you drive slowly. But it's also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. Somewhat disturbing is the squeaky gas heater and the fact that the water temperature in the shower fluctuated quite a bit. Maybe it can still be repaired. But that's whining at a high level. All in all, a great place to stay with a very nice and accommodating host.

Palazzo del Taja - in the center with whirlpool
We absolutely loved this apartment, which is centrally located in a pedestrian area within easy walking distance of all the sights in Siena. The apartment has excellent air conditioning—essential during the summer months—and is in immaculate condition, with a modern and spacious feel. It had everything we needed for our stay, although we didn’t spend much time indoors as we were keen to enjoy everything beautiful Siena has to offer. Communication from Ricardo was excellent throughout. We had a hire car to explore the wonderful Tuscan countryside, and Ricardo helpfully arranged an underground parking space for us, just a 10-minute walk from the apartment, at a cost of €15 per day. We would highly recommend both the apartment and Ricardo!
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.

Charming Castle
I have stayed at 50+ AirBnB and this was my all time favourite. Imagine staying within a castle, with an adjacent church, a great pool and the most fabolous views of the umbrian country side. Not to forget the best equipped kitchen and the best care taker Nazareno. And an actual fresco in the bedroom! Cant recommend this place enough.

Tranquility and Well-being [Lake Trasimeno]
Monica and Renato are fabulous, friendly hosts. The apartment we rented was spotless. Bed was very comfortable so we had a great nights sleep. You are adjacent to other apartments but there is no noise at all from your neighbours, nor were we overlooked. The views from the small terrace were stunning, over the colourful garden to the vineyards and Tuscan landscape beyond. Bliss. The swimming pool is available for all to use. Our hosts left a lovely bottle of Prosecco as a welcome as well as coffee, oil, vinegar, breads, jams etc Thank you Next time we will stay longer!

San Rocco – Bellavista – Castello di Bossi
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended

Relax between Siena and Valdorcia
I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!

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.

Ginestra: Private Pool Overlooking Florence
Rafaella's place was nothing short of amazing! We had such a great time her place had everything you could need and more. She and her husband were super responsive. My only wish is that I wish it was warmer so that we could have enjoyed their beautiful outdoor space more. They even gave our girls sweet easter eggs. Thanks for letting us stay in your lovely home.

Apartment with terrace and stunning view
Staying at Raisa's was incredibly nice. The accommodation and especially the view is much nicer than shown in the pictures. Raisa went to great lengths to make everything as pleasant as possible for us. The dogs (Saila and Yango) are mega cuddly, the pool is great and the whole property is really picturesque. By car, beautiful city trips, etc. are easily doable and we would be happy to come back again sometime.
Quick stats about condo rentals in Montepulciano
Total rentals
30 properties
Nightly prices starting at
G$8,373 GYD before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Lake Trasimeno
- Lake Bolsena
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Santa Maria della Scala
- Terme Dei Papi
- Basilica of St Francis
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- Pubblico Palace
- Castiglion del Bosco Winery
- Mount Subasio
- Cantina Colle Ciocco
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Cantina Contucci
- Madonna del Latte
- Abbey of Monte Oliveto Maggiore
- Poggio Talamonaccio
- Podere Il Cocco