This Medieval hilltop town in Tuscany Montepulciano, Italy boasts some of the most incredible panoramic views. This area is known for the wine it produces, so you could choose to go on a wine tour, explore the impressive sights of Chiesa Del Gesu. Or if none of that tempts you then you can simply sit and order a cup of coffee in the Main Piazza whilst people are watching on the bustling streets. There are so many unique features in Montepulciano that you’ll soon be asking to extend your stay! To help you find the ideal base, we’ve searched far and wide to come up with the top ten Airbnb vacation rentals.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2024.
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1. Pure relaxation with stunning views (from USD 64)
This room in the hosts’ beautiful traditional-style house has its own entrance. This room is located in an ancient watchtower in the pure countryside which you can enjoy from your very own garden. The vistas of this property are stunning and are dotted with olive groves. If you are looking for tranquility, then you’ll find it here. The double bedroom has a private bathroom and a kitchenette facility which include a coffee machine, an electric plate, and a kettle. This should be enough to prepare breakfast and lunches. Dinner options can be reached in the historical center of town which is 15 minutes away on foot or 3 minutes by car.
Top guest reviews
Host:
ave had helpful maps of the cityave was one of the friendliest hosts we’ve metave was a very kind and welcoming hostshe's a great host and very helpful with local tipsave is such a warm gracious hostLocation:
perfect location in a beautiful housebrilliant location 15 min walk from montepulcianoperfect location to explore tuscany by carvery close to the beautiful town of montepulcianothe location is peaceful and relaxingCleanliness:
everything was clean and the room is quite spaciousthe room itself was clean and spaciousthe room is very clean and comfortableave's rooms are excellent clean and quiet and nicely decoratedplace was very clean with lots of thoughtful touches throughoutRead more reviewsAmenities & Room:
very cozy and comfortable room with all necessary amenitiesave was very sweet and thought about the details (fan treats coffee map)the property and views are amazing and the room is quaint and quietgorgeous courtyard and view out the front which was perfect for breakfast and drinksnot air conditioned but didn’t need it as the room remained cool despite the heat
2. La Piazzetta (from USD 217)
This open-plan apartment is in a fantastic location, just 250 meters (820 feet) from Piazza Grande. This listing also features panoramic views of Valdichiana, Trasimeno, Montepulciano and Chiusi Lakes. The property itself features bright decorations throughout. The high ceilings and archways make the property feel very spacious. There is a double room and an additional sleeping option of the sofa bed if needed. It is worth noting that the accompaniment of a third person might be at an additional cost and there is a minimum stay of two days. There is a kitchenette area in the property so that you can make light meals. There is also free parking just 80 meters (262 feet) away.
Top guest reviews
Host:
host very helpful and accommodatinggiuliano is an amazing hostyou are a wonderful hostgiuliano is a wonderful hostgiuliano is a wonderful host attentive to his guests needsLocation:
the location was beyond perfectguiliano's apartment is located in the most perfect location in montepulcianoeasy walking distance to the entire citythe location is great with access to the main shopping areas right out your dooreverything about it and the location were amazingCleanliness:
really clean the placeentire space was clean and well thought outsparkling clean beautiful shower and comfortable bedthings to clean up with in the kitchenthe apartment was very clean and stocked with food and everything you would needRead more reviewsAmenities & Room:
perfect view from the living roominside is comfortable with all the amenities one needs with a great view from the kitchenthe cozy apartment has a beautiful view many amenities and a wonderful attentive hostthe heater was perfect and the shower also perfectthere was no flaw in the apartment and giuliano is fantastic
3. Montepulciano: living the history (from USD 87)
This classical and elegantly renovated loft in the historical center of Montepulciano boasts views over the rooftops. The property has two bedrooms, one single and one double, both of which are of a good size. The master bedroom features a fireplace and modern a bathroom. Located on the second floor (with 70 steps and no lift) of a 1500-year building, directly on the main ‘Corso’, you have everything you could need right on your doorstep. The property is wonderfully bright and welcoming and there are a few different parking options nearby, but take note that these are outside the historical walls as driving in the center of Montepulciano is not allowed.
Top guest reviews
Host:
tiziana and marino were wonderful hostshosts were very good communicatorstiziana and marino were wonderful welcoming hoststiziano and marino were wonderful hoststiziana and marino were wonderful hosts they were welcoming and so helpful when we had questionsLocation:
perfect location for walking in town and close to restaurantsthe location is idealthe location is perfectbeautiful location in the middle of the towngreat location in the heart of the townCleanliness:
very clean and well appointedthe apartment was clean and homeythe apartment is clean and modernthe flat is clean and well appointedthe apartment was spotlessly cleanRead more reviewsAmenities & Room:
the apt fit and finish was impeccablevery hot would be nice if there was at least a fan or acthe place itself is very comfortable lots of space well heated good wifi bathroom even has a washerwifi wasn't great but otherwise superb great introduction to the property by tziana's friendthere are a few stairs but the view over the rooftops from the apartment is wonderful
4. The Little Arch of Memory apartment
Just a few steps away from the main square you’ll find this adorable first-floor apartment that has a bedroom, a kitchen, and a toilet. Although near the main square, it is a few rows back so it is not too noisy here. This property is most suited for a couple. There is an adjacent property that is available for an extra charge and can host one adult and two children of up to 12 years old. This property is decorated in true Tuscan style with wooden ceiling beams throughout. There is a partial view of the Val di Chiana and the Apennines Mountains. You can also request to rent the wine cellar below the property if you wish.
Montepulciano, Toscana, ItalySuperhost
Accommodates: 2
Top guest reviews
Host:
elias was a lovely hostelias was a great hostelias is a wonderful hostelias was a great host who provided excellent recommendationselias is a great hostLocation:
the location is great just 30 seconds from the main squarelocation is perfect as it is just located in the heart of montepulcianothe apartment has a fantastic location close to everythinggreat location and exactly as describedincredible location a great place to come back to while exploring tuscanyCleanliness:
the place was very clean and decorated beautifullythe apartment was clean bed comfy and bathroom spaciousit was very clean and had a comfortable large bedthe apartment was clean comfortable and well situatedthe apartment was precisely as described on airbnb very clean and furnished lovelyRead more reviewsAmenities & Room:
the apartment has complete temperature control with efficient central heating and air conditioningvery charming apartment with nice view from the kitchen window of sunrise and sunsetthe apartment is beautiful and had all the amenities we needed for our staywifi washing machine air coolers and shower works perfectly as do everything in the kitchenthe apartment is very nice with a beautiful bedroom nice kitchen and bathroom with all amenities needed
5. A view from the top (from USD 152)
Nestled in a side street just 250 meters (820 feet) from the Piazza is this two-bed apartment. Both of the bedrooms are double in size and each has access to their own bathrooms with showers. There is a spacious and elegant open-plan kitchen/living room area. The kitchen comes equipped with a dishwasher, washing machine, microwave oven, toaster and even the all-important coffee machine. This aptly named apartment also offers incredible panoramic views from the top. Guests will be able to drive through the security gate and park the car directly outside the front of the house.
Top guest reviews
Host:
luca was a great hostluca was a great hostluca was a great host offering helpful travel adviceluca was a great hostsluca himself was the perfect hostLocation:
so comfortable and perfect location in montepulcianolocation is great to walk around the main area of montepulcianowe loved being able to walk to everythingthe location of luca's apartment is perfect we loved the easy access to the beautiful town of montepulcianothe location is ideal for getting in and out of montepulciano for day trips around tuscanyCleanliness:
clean cozy and very welcomingvery clean & very comfortable bed would definitely stay here againthe place is very up to date and cleanit was very clean and had all that we needed to cook at the apartementboth bathrooms were exceptional and the entire space was cozy clean and comfortableRead more reviewsAmenities & Room:
the view - jaw-dropping unobstructed view to enjoy from small balcony with table and chairswe appreciated the ceiling fans and open-air conceptthe view alone was worth the stay the home was also comfortable and had all the amenities we neededthe views from this apartment are amazing great quiet location with all the necessary amenitiesamazing apartment with the most relaxing views
6. Il Leccio Tuscan Farmhouse
If you want to experience a traditional Tuscan location then the Il Leccio Tuscan Farmhouse might be your ideal vacation rental. The property, which can comfortably fit two people, is what we would call authentic, rustic and chic. The open-space design of the ground floor allows plenty of light in and this bounces off the woodwork pieces. This recently renovated property has rustic terracotta floors and traditional furniture. You’ll experience the true face of Tuscany.
Montepulciano, Toscana, ItalyAccommodates: 2
Top guest reviews
Host:
aebano was the perfect hostaebano is a wonderful hostaebano is a great and thoughtful hosthost provided great advice on the local attractionsour hosts were amazing and beyond helpfulLocation:
the location was great and close to the city center and the wineriesbeautiful location just outside town in the middle of vineyard and olive groveexcellent stay in a dreamy location wonderfully located in the tuscan countryside it’s perfectthe location is perfect with just a 5 minute drive to the center of montepulcianounique farmhouse apartments with amazing atmosphere and great location (5 mins away from montepulciano)Cleanliness:
the space was sparkling clean and had lots of charmvery spacious and cleanvery clean and great amenitiesthe apartment was as described and cleanRead more reviewsAmenities & Room:
charming comfortable farm house with beautiful view of tuscanythe wifi didn’t work when we tried but that was not a bother for uscomfortable bed and good coffee making supplies i recommend this place for a rich experiencethe shower had great water pressure and the bed slept comfortably
7. Letizia's home (from USD 98)
This homely property is shared with the host and you will be renting the spacious double bedroom. It is worth noting that this is separated from the main living quarters by a ¾ wall. As a guest, you’ll have access to the open-plan kitchen/living room, dining area, shared bathroom, veranda and spacious patio. The garden with BBQ setup is also available for guests to use. It is just 1.2 miles (2 km) from the historic center and near panoramic views. There is a reserved parking spot at the front of the apartment for those coming by car.
Top guest reviews
Host:
she is an efficient hostgreat place with a great hostletizia and her mother ivana were gracious hoststhe greeting was friendly and welcomingour hostess ivana was very kind and helpful upon our arrivalLocation:
great location just outside of townvery good location to visit montepulcianoyou may walk or drive even take a bus to the centre easilythe place is little outside the city but perfectly reachablethe place is very cozy and the garden is great - must be perfect in summerCleanliness:
the apartment is clean spacious and well servicedthe apartment is spotlessly clean and well equipped with dishes pots and pans and breakfast food itemsletizia is very friendly and the place was nice and cleanthe house was very clean and well organized and we really enjoyed our staythe place is very quiet spacious well equipped very clean with a nice gardenRead more reviewsAmenities & Room:
we had some unseasonably cold days and needed to use the heater which worked very wellwe were welcome with a snack and the apartment is beautiful and bigthe flannel sheets are so comfortablewe had a beautiful spacious kitchen bedroom sitting room sun room and bathroomletizia was kind enough to start us off with coffee and bread for the first breakfast
8. La Corte Segreta (from USD 124)
Near the Tower of Pulcinella and the main Square, this guest house vacation rental offers a relaxing room for your holiday. The double bedroom is spacious and elegantly decorated in a chic style. The crisp white decorations are offset by the deep wooden furnishings in a perfect contrast. The property has private access through a ‘secret alleyway’. Panoramic views can be enjoyed from the shared access garden on this property. Sounds like the perfect spot to watch the sunset on your holiday.
Top guest reviews
Host:
laura was a wonderful hostmarco was a great hostowner marco is very welcoming & helpful with recommendationsbrilliant stay with lovely hostsgreat place to stay- the hosts are welcoming and helpfulLocation:
great location if you want to be in the middle of the citythe location of this room is excellentgreat location great room comfortable bedgreat location in montepulciano marco was vey welcominggreat central location but just removed enough from busy streetCleanliness:
room was spotless cleanroom was very clean and included cleaning service while we were out during the daythe room was clean and comfortablea quaint and clean room to staybeautiful clean room just as describedRead more reviewsAmenities & Room:
marco brought us an extra fan which made the room more comfortablea real tuscan villa with a beautiful view and an amazing roomwifi was the best we have had out of all the places we have stayedbeautiful room in montepulciano you have your own private patio bathroom and bedbathroom ensuite was also very nice
9. Apartment il Torrino (from USD 147)
If you are looking for unparalleled views then your mission is complete. We don’t think you’ll be able to beat Torrino. This completely renovated property boasts views of the Valdorcia hills and the Temple of San Biagio. Located in close proximity to the Piazza Grande, the Poliziano Theater, and the Fortezza, this means that you can reach all the landmarks easily. There are two bedrooms, one of which has a traditional double bed whilst the other has a double sofa bed. There are also two bathrooms, a well-stocked kitchen, and full WiFi. Finally, the living room area features a flat-screen television and parking is just 10 meters away (32 feet).
Top guest reviews
Host:
claudia was very helpful and responsiveclaudia was most helpful and accommodatingclaudia was very helpful and really nice personclaudia was an excellent hostclaudia was very helpful and even though we arrived later than planned she was there to greet usLocation:
the location is greatsuper close to the main street with good food and wine bars nearbyyou will love this locationparking was convenient right in front of the place and great location walking distance to shops and restaurantsfantastic outlook very comfortable and relatively easy walk to everythingCleanliness:
very clean and well maintainedthe apartment was clean and spaciousthe place is well laid out clean and functionalthe apartment was very clean and has perfect locationit was perfect for our group of 4- plenty of clean linens and towelsRead more reviewsAmenities & Room:
the wifi worked very wellbeautiful apartment with stunning viewslarge yet cosy apartment with beautiful views and great amenitiesthe view from claudia's apartment is outstandingthe apartment of claudia is amazing with a beautiful view on toscane landscape
10. Family apartment (from USD 63)
This unique mezzanine-style vacation rental includes a kitchen, bedroom, private garden and free WiFi throughout. Protected by a fence, this property is ideal for a couple with a young child as there is also a crib on site. The historic city center is only a few minutes away on foot, or you can use the shuttle bus.
Top guest reviews
Host:
our hosts were a warm and friendly couplewe enjoyed the privacy and the hospitality of the hostsfriendly and easy to communicatedebora is a very kind and helpful hostpeople are friendly and prices are very fairLocation:
wonderful location walking distance to historical city center and to a supermarketthe price and location are very goodshort walk (20 minutes) up the hill to the grand piazzathe flat is exactly as described and the location is excellenthospitable owners excellent location and value for moneyCleanliness:
clean and well furnished apartmentthe place was clean and cozythe apartment is clean and cozy has everything supplied that you might needthe space is cozy and clean and our daughter loved the swing in the yardgreat value strong recommendation for this clean up to date spacious and central locationRead more reviewsAmenities & Room:
the kitchen had everything internet was great to havethe kitchen/living room is adorable and debora provides a bottle of water and a carton of milkthe apartment was a short walk with gorgeous views to the old citythe bed is comfortable and there are extra blankets availablethe apartment has every type of household appliance and the place is amazing calm and beautiful
Plenty to see and do
There is so much to see and do that even the kids will have a great time exploring. Remember to book online and be sure to tag us on your Instagram photos. We’ll be waiting!
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