Overlooking the Val di Chiana and Val d’Orcia, the ancient town of Montepulciano is located on a hill which is surrounded by olive groves, vineyards, and forests of pine and chestnut trees. Renowned for its pork, cheese, “pici” pasta, lentils, and honey, this medieval hill town is frequented by travelers looking to unwind. Tourists can pay a visit to the Piazza Vittorio Emanuele, which is commonly known as the Piazza Grande, from where they can admire the stunning views of the Tuscan countryside. Art lovers will have a gala time at the Museo Cívico (Municipal Museum), which boasts archaeological finds, paintings of the medieval and Renaissance periods, and a number of fine terracottas by Andrea Della Robbia. The Cathedral of Santa Maria Assunta is an oft-visited destination and is revered by many. Visitors planning their vacation in May can be a part of the Fiera Delle Tre Berte festival, where they can get a chance to sample typical food items and local delicacies, including Montepulciano wines. Montepulciano is a vacation paradise and no holiday is complete without a comfortable stay in a world-class rental. Here’s a look at the top 10 best Vrbo vacation rentals in Montepulciano, Italy.
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. Great accommodation for a relaxing holiday (from USD 115)
Located only a few blocks away from the historic center of Montepulciano, this farmhouse-style rental offers accommodation to six guests. Spread over two levels, this property is fully fenced which makes sure that guests are safe and secure. Guests can bask in the sun in the garden area, featuring a gazebo and deck chairs. If you are not in the mood to hop out, plan a small barbeque night or just sit back and relax in the outdoor seating region. Travelers with children need not worry, as a highchair, crib, and books might come handy here. This house is easily accessible from the city’s public gardens, shops, restaurants, and the bus station.
Top guest reviews
Host:
He was gracious and showed us the ins and outs of the house and told us to contact him with any questions He also made some wonderful restaurant recommendationshe also replied straight away to emails and always answered the phonethe owner met us upon arrivalour host was most accommodating and couldn't have been more charmingthe host is the most friendly and helpful guy ever met and took care of us anytime Thanks again for everythingLocation:
This lovingly restored property is conveniently located about a 15 minute walk from the Montepulciano city centeris within a 5min walk:Be aware that the walk into Montepulciano includes a very steep walk uphill (but the walk is well worth it )and it's an easy walk into the town of Montepulciano which has a ton of amazing restaurantshowever there is a bus stop right around the corner which has a connection to the trainCleanliness:
The house was very clean when we arrived and the house was big and comfortable enough for us (4 adults and 2 children)EverythingIt was spotlessly clean and well appointedThe house is beautiful to say the leastRead more reviewsAmenities & Room:
The kitchen living roomThere are two double bedrooms and the bathroom with shower on the up floor which you can access from the front doorsThere's plenty of storage and comfortable bedsThe house is more modern and more beautiful than I expected from the picturesThe air conditioners are in every room
2. Apartment for two people (from USD 65)
Ideal for two people, this apartment offers a living room, a fully equipped kitchenette, and a large bedroom with a private bathroom. Availability of kitchen amenities like stove, utensils, refrigerator, and a coffee maker allows guests to prepare their own meals and enjoy them in the comfort of their own dining area. The free Wi-Fi connection will keep you updated daily and will help you locate nearby hotspots for local sightseeing. If you are traveling by car there is no need to worry as free parking space is provided on the premises upon your arrival. The Piazza Grande and the Duomo are located nearby to this property.
Top guest reviews
Host:
Bellissimo appartamento nel centro della splendidaOur host was in Milan when we arrived Simone checked us inand yet Simone was waiting for usand I was met promptly upon arrival with the keysCute cozy beautiful viewsLocation:
The apartment was perfectly located inside Montepulciano Communication was excellentOttima anche l'assistenza della proprietaria Speriamo di tornarci prestoThis is a lovely little apartment in a perfect setting within the historic center of Montepulciano Communication with the owner was very goodThe location was perfect and the price is greatl ora di tornarci proprietari professionali e molto disponibili ad ogni esigenzaCleanliness:
The apartment was perfectly clean and had everything I needed for a week+ stayRead more reviewsAmenities & Room:
The views from the room were amazingThe accommodations were adequate and the pastoral valley view was wonderfulDo check on parking and driving regulationsand we were able to park right next to the apartmentAbbiamo sogiornato nel periodo di capodanno in questa comoda
3. Holiday home with splendid views (from USD 180)
Situated in the highest point of the village of Montepulciano, this property sleeps six guests and it is surrounded by the Medici fortress and the Piazza Grande. Built on the foundations of an old local house, this stunning masterpiece offers splendid views of the Valley di Chiana, from Trasimeno Lake until the Marche Apennines. With a lounge, a lovely private garden, bedrooms boasting stylish furnishings, beamed ceilings, and a private bathroom with a shower, this rental provides lavish comfort and a relaxing stay to its guests. Pets are welcome here on prior notice. Shops, restaurants, and historic wineries are easily accessible from here.
Top guest reviews
Host:
First of all David & Rafaella are amazing hostsOur hosts were wonderful and so friendly and helpfulRaphella and David were so helpful and a delightful coupleOur host family were so sweet but unobtrusiveThey greeted us upon arrival and set up all our dinner and lunch reservations which was so helpfulLocation:
The old town section of Montepulciano where the property is located is charming with numerous restaurants and shops all within an easy walkThe location is excellent for walking to everything and right next to a beautiful parkAn amazing location in a simply beautiful townThe Pileggi's were the bestThis apartment is in the BEST location adjacent to a beautiful public garden with birds chirping and the corso (main street) AND Piazza GrandeCleanliness:
It was beautiful clean and conveniently locatedThe location can't be beatThe beds were comfortable and cleanThe apartment is beautifully decorated old world charm but modern touches and very cleanRead more reviewsAmenities & Room:
The beds were very comfortableThe apartment was immaculate and the beds were very comfortable with great pillowsThe property was immaculate and beautifulThe Bathrooms are well appointed larger showers and plenty of hot waterThe onsite parking was great and a real plus in the old city
4. Apartment near Piazza Grande (from USD 115)
Enjoy your stay at this refurbished apartment, which allows four people to dwell aboard. If you are too lazy to go out just sit back and relax in the balcony while admiring the incredible view that extends from the Temple of San Biagio to the Val d'Orcia. Guests can also cook their own meals and relish them in the comfort of their own porch region, or they can gossip over a glass of wine in the lawn area. Long-term renters are welcomed here on prior notice. Free car parking on the premises is also available. This apartment is only a few meters away from the Piazza Grande, the Poliziano Theater and the Fortezza.
Top guest reviews
Host:
The host was accommodating with are arrival timeGrocery store with fresh food around the cornerwe hit traffic due to snow storm and she was able to meet us at our new timeWe love this apartment we have stayed before and always enjoy every minuteThe apartment is clean and well equipped as promised (pots fridge stove and utensils) and the host is very attentive we did not have any concerns during our stayLocation:
Parking super convenient Views from upper & lower patios are panoramic & beautiful Walking anywhere in the cityVery well maintained Ideal location for getting up to the city by caris super convenient from the housePerfect location great view from the terrace Claudia was very helpfulCleanliness:
The apartment was very clean and fully equippedRead more reviewsAmenities & Room:
The view from the terrace is breathtakingTherese is nothing to complain aboutOur favorite part of the property was the sunsets from the upstairs deck breathtakingOnly one sad thing: we had to leave
5. House with a beautiful garden (from USD 98)
Located in the city center, this beautiful house is close to the historic city wall and provides accommodation to six guests. Cook your meals in the fully equipped kitchen and relish them in the large patio area featuring a table and umbrella. Sit back and relax in the garden region and gorge over the stunning views of the surrounding valley. Amenities like a washing machine, Wi-Fi connection, refrigerator, coffee maker, and TV are available here to make sure guests have a comfortable stay. If you are visiting during the Christmas and New Year season, do not forget to visit the Christmas market.
Top guest reviews
Host:
Excellent check in and check out most beautiful views in the morning and eveningsperfect location and a wonderful town boasting great wine and food a music academy museums and medieval housingPaola is an wonderful hostThe home was beautiful and had all the charm of a home in an ancient hill top town you would expect and it was close to all the shops and restaurantsWe visited Easter weekend and the town was very festive for the holidayLocation:
Everything in town is easy walking distance and it is possible to park just outside the closest city gate just a minute or 2 from the housebut if full you have to park up a steep gravel drive to a park Houseit's close to everything reallyBeautiful home and property Conveniently located in the city Beautiful views by day and extremely quiet at night Would definitely stay here againThe patio is great to lounge around and the view is amazingCleanliness:
the apartment is fully equipped and was very cleanRead more reviewsAmenities & Room:
Spacious comfortable with a fully stocked kitchen and even a dining roomA car is necessary to explore Tuscany but with the included parking pass you can use this as home baseas well We will be greatful forever for the wonderful memories we have of our time in your house Paolaso you can park the car not too far awayIt is well equipped and comfortable with beautiful antiques throughout
6. Historic dwelling with a terrace (from USD 115)
La Casina Toscana is an ancient property from the 19th century, and it offers accommodation to six guests at a time. Head to the terrace, where you can taste a glass of good wine while watching the splendid panorama of the Val di Chiana. Guests can also relax under the gazebo in the garden region with their loved ones or can plan a small barbecue night. Availability of a TV, Wi-Fi connection, books, and DVD player makes sure that guests can be entertained during the entire trip. Sports lovers can head to the tennis court or the golf course, which are only 100 meters (328 feet) away.
Top guest reviews
Host:
He was very responsive when we needed help with a couple of requestsso he came and got us and led us to itwas a very attentive hostThis property exceeded our expectations Davide was a wonderful host and the property is more beautiful than the picturesVery well decorated Excellent maintenance Lovely outside areas (3) Wonderful and attentive hostLocation:
It is in a great location for exploring the city of Montepulciano and the Tuscan area in general Walking distance to grocery storesLocation is a 10 out of 10 walk to town walk to grocery storeThe bus station is within walking distance and a modern Conad grocery storeLovely house in perfect condition just outside Montepulciano (within walking distance)A local bus runs from the nearby bus station up to and through the cityCleanliness:
The place is clean as a whistle and Davide (and parents)The place was very clean and more than adequately furnishedWe found it extremely comfortable and didn't want to leaveGrazie mille per una meravigliosa vacanzaI cannot say enough about this propertyRead more reviewsAmenities & Room:
a living/dining roomIt is cozy and warmWe were driving a leased car and were please that free parking was included on sitecomfortable bed and utilities are goodThe other couple staying with us had to go downstairs to have their own bathroom
7. Two-bedroom residence with countryside views (from USD 120)
Nestled in the core of Tuscany, this renovated apartment offers two living rooms, two bathrooms, a kitchen, and balconies. Suitable for six people, this property provides both the views of the surrounding countryside and the old part of Montepulciano and its city hall tower. Free car parking is not available on the premises but visitors with a car need not worry as free public parking is only 30 meters (98.4 feet) away from here. If you are in the mood to explore the city, locate the nearby hotspots via free Wi-Fi connection and avail the bus from the station, which is only 100 meters (328 feet) away from this rental. This Vrbo accommodation is easily accessible from shops, food markets, local market (Thursday), bars and restaurants.
8. Spacious villa near the vineyards (from USD 292)
This charming three-tier property is an ideal accommodation for 10 people, and it is situated in the sun-kissed hills of Montepulciano. Located just outside the Medieval City walls, guests can enjoy the spectacular views of the olive groves and vineyards, from the comfort of their own balcony. Head to the French doors leading to the large terrace, where you can lounge under the Tuscan sun, on a comfortable chaise while capturing stunning pictures of the three lakes - Lago Trasimeno, Lago Montepulciano, and Lago Chiusi. If you are not in the mood to just sit back and relax, take a walk down to the medieval town center. Here you can explore the 16th-century monuments, and local specialty shops, or sit in the main square to drink an Italian espresso and listen to a free classical music concert.
Top guest reviews
Host:
Erika was such an awesome host giving us tons of helpful info before we arrivedand she was so patient and accommodatingnobody came close to her making us feel so "in the know"Her home is gorgeous with breathtaking viewsI did not know anything about the Tuscany regionLocation:
Beautiful scenes and a little chillyIt is walking distance to the best restaurants and shops in MontepulcianoIt is also not far from Florence and an easy drive to Pisa and LuccaThe property was conveniently located within minutes walking distance of town square Montepulciano and all the shops restaurantsThe restaurants were all amazing and within a 5 - 10 minute walk awayCleanliness:
The villa was clean extremely spacious and offered amazing views of the countrysideThere were 4 of us and the showers were hotdishwasher refrigerator and full kitchenThe views of the deck are spectacular and Erika's home was very comfortable and cleanAlso mention of water pressure which was low in the downstairs shower but adequate especially when you consider the locationRead more reviewsAmenities & Room:
The beds were comfortable and the kitchen was stocked with everything that we needed to cook dinner in one nightthe spiral staircase is a little trickythe bedrooms had nice beds and large windowsThe villa came equipped with a washing machineThe kitchen was well equipped and the house had plenty of space to relax
9. Charming family cottage (from USD 53)
If you are looking for a safe and secure property for your children, this small apartment is the perfect holiday retreat in Montepulciano. With a small entrance room, this rental is located on the ground floor of a family cottage and it is suitable for three people. Guests can enjoy gossiping on the porch over a glass of wine, or can just take a leisurely stroll with their loved ones in the garden area. Travelers with children need not worry as a high chair may come handy over here. Pet lovers are also allowed to bring their pets along with them on prior request. The historic center of Montepulciano is only a short walk away from here.
Top guest reviews
Host:
The proprietor Debora was extremely helpful and pleasant Prior to our arrival she contacted us about the limited bus schedule in effect that day which saved us a lot of aggravation and moneyShe even picked us up from the bus station so that we wouldn't have to walk with our luggageShe and her parents (who live upstairs) made everything seamless and easyvery clean and well-equippedLocation:
The apartment is located in a quiet neighborhood about ten walking minutes to the historic center of Montepulcianobut it only takes about 10 minutes to walk to the beginning of the historic centreThere is a bus stop a few meters from the gateluogo molto rilassante a due passi dal centro storico di MontepulcianoThere are lots of wonderful places to visit nearby if you have a carRead more reviewsAmenities & Room:
It is cozy comfortableVery friendly owners and a well equipped apartment on the ground floor of a pleasant detached house in a quiet area of the townExcellent apartment for convenience equipment and comfort
10. Villa with wonderful views (from USD 67)
Overlooking the medieval town of Montepulciano, this spacious villa is an ideal holiday retreat for a maximum of seven people at a time. Guests can bring the grocery items from the nearest supermarket, which is only a 10-minute walk from here and can use them to prepare yummy delicacies. If you are not in the mood to go out, gaze at the stars while lying down on the wet grass, or gather around the fireplace for a cozy evening. Bicycles are available on this property, and you can take them to explore the neighborhood brimming with legendary local cuisine, and the unique artistic heritage of Tuscany. This rental is only 5 minutes’ walking distance from the bus station and tennis courts and quite close to Umbria and Trasimeno Lake.
Top guest reviews
Host:
The property owner was very welcoming and helpful when we had to contact her to ask for information about services in the areaSpectacular Resting made easykitchen well equippedLoved having a walkout to the gardenYour home away from homeIf the property owner would update the mattress it would be a total winnerLocation:
then bus and the owner will gladly pick you up from the station if neededit is the only way in my opinionMany thanks to Magda and Ugoand It's very easy to access of Montepulciano center to the another hand Owner familyPosto fantastico e proprietaria molto disponibileRead more reviewsAmenities & Room:
When researching it more and having loads of luggageIt is very spacious with a good outdoor space with excellent views of montepulcianoGreat apartment with a wonderful view of MontepulcianoThe only reason I can't leave a 5 star review is because of the bed in the master bedroomthen one came on automatically Very dark parking and walking to door
Stay in beautiful Montepulciano
Montepulciano is well known for the architecture of its medieval buildings, charming squares, and vast panoramas. Perched on a reclaimed narrow ridge of volcanic rock, the town is the perfect base to explore the Tuscan countryside. With picturesque landscapes and enchanting villages, this place has received notable attention after the filming of the vampire saga Twilight sequel, New Moon. Henceforth, Montepulciano awaits with open arms to welcome one and all.
History
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