Apartment holiday rentals in Montepulciano

5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!

Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!

Great location! Centrally located near Piazza Grande. Steps away from shopping, restaurants, and incredible views of the countryside. Apartment was very comfortable. Perfect for a solo traveler. Updated bathroom and shower was great. Overall, the entire apartment was clean and well appointed. Elias was awesome. Incredibly responsive and helpful. Provided several recommendations of things to do within Montepulciano but also gave insights on other nearby towns. He texted me a few times during my stay to see how I was doing and if I needed anything. Very gracious. Overall great experience.

We loved our stay at Marco’s. The cottage, pool, location were wonderful and the views amazing. Perfect way to end our vacation. Very thoughtful with snacks and drinks provided. .

I can’t say enough about our hosts! They were communicative from start to finish and our experience would not have been the same without them. Our favorite part was doing the cooking class and having dinner with them and their family.

Spacious place in an amazing quiet old medieval town. Spectacular view off the little balcony. Highly recommend!

We really enjoyed our stay at this really unique accommodation. It is located in a medieval village, high on a hill. The apartment is compact, but has everything you need. The view from the balcony is fantastic. Malgorzata was a great host and very responsive when we had questions. I would not hesitate to recommend this property.

Great stay with incredible views. Perfect location for exploring Montepulciano and the surrounds. Parking was easy and everything was really comfortable.

We had such a wonderful six days at this beautiful place. It was comfortable and one of the most picturesque properties we’ve stayed at in a long time. We fully enjoyed the barbecue area, walking the trails, and all of the special views from our room. Nico and Elena were such gracious and lovely hosts - we appreciated such wonderful hospitality.

The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.

Wow what a fabulous stay ! San Gusme and its surrounding area is beautiful and we felt so lucky to be able to stay in San Gusme itself . Elvira was super helpful and had great local recommendations for wine tasting etc .

We had a wonderful 4 day stay, thank you for your hospitality, to all the staff and family. First class, recommended restaurants plus made reservations for us, which were needed, and recommended sites to visit. Rooms were spacious and clean, grounds were beautiful, wine tasting and Stephan’s knowledge of wine making made the tour. We also had breakfast every morning, and one evening had a dinner, recommended. A beautiful couple, so glad we meet them. Hopefully we will be back again.

AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.

My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

Dorita is a Super Host, she is the sweetest & kindest person. She went above and beyond to help us with our luggage since we arrived early before check-in. She met us at the beautiful property and explained everything we needed to know and gave us great recommendations for things to do and delicious restaurants. The apartment was absolutely beautiful, a Tuscany charm with a private terrace that had beautiful views. The beds were very comfortable and the bathrooms were large. She was always there for us when we had a question and responded immediately she even found us a taxi to take us to the train station. This property is quite a charm, and we loved it. You can walk right out the front door and be in the beautiful city with lots of shops and Restaurants and taking in the beautiful views of the city. We highly recommend this beautiful property and Dorita. When we return to Italy, we would stay here again.

Wow! What a great place. Francy is a wonderful host. She went above and beyond to help us make our time in Montepulciano comfortable and memorable. This remodeled gem in the heart of Montepulciano was created in a very thoughtful way. Two separate bedroom suites with view, great air conditioning, comfortable beds. And the kicker is the upstairs roof-top balcony with breath taking views over the town and beautiful countryside. Well done Francesca! Thank you!

Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.

Apartment as described. Very clean and comfortable. The center is a 10-minute walk away. Always top-notch and very kind communication. When I return to Florence, if there is the possibility, I will return to this apartment.

After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!

Excellent location and beautiful apartment. Easy to get in self-check in and good communication with the host. Great kitchen, stocked with all the hardware you need. Common area was comfortable for the 4 of us. The view is amazing. Balconies on the water with close up views of Ponte Vecchio. Definitely one of the best places we've stayed in a 20 day trip in several cities.

Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!

Fabrizio was very quick to communicate and kind, and gave great restaurant recommendations. The apartment was very clean and is very well located

We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.

Martina's place was a great rental in central Florence. Close enough to walk to major landmarks and the central train station. The place has everything you need and more. We were met by Martina and her friendly dog on arrival. She is very friendly and hospitable and took her time to show us her home and give us lots of information on the area and suggestions. I would recommend this rental to everyone!