10 Best Vrbo Vacation Rentals In Montepulciano, Italy - Updated 2021

vrbo montepulciano italy

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.

1. Great accommodation for a relaxing holiday (from USD 157)

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.

Single house in an exclusive place to spend a relaxing holiday in Tuscany
26 reviews
chateau / country house 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen living room
There are two double bedrooms and the bathroom with shower on the up floor which you can access from the front doors
There's plenty of storage and comfortable beds
The house is more modern and more beautiful than I expected from the pictures
The air conditioners are in every room
The house was very clean when we arrived and the house was big and comfortable enough for us (4 adults and 2 children)Everything
It was spotlessly clean and well appointed
The house is beautiful to say the least
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 recommendations
he also replied straight away to emails and always answered the phone
the owner met us upon arrival
our host was most accommodating and couldn't have been more charming
the host is the most friendly and helpful guy ever met and took care of us anytime Thanks again for everything
This lovingly restored property is conveniently located about a 15 minute walk from the Montepulciano city center
is 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 restaurants
however there is a bus stop right around the corner which has a connection to the train
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2. Apartment for two people (from USD 78)

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.

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
14 reviews
Apartment 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The views from the room were amazing
The accommodations were adequate and the pastoral valley view was wonderful
Do check on parking and driving regulations
and we were able to park right next to the apartment
Abbiamo sogiornato nel periodo di capodanno in questa comoda
The apartment was perfectly clean and had everything I needed for a week+ stay
Bellissimo appartamento nel centro della splendida
Our host was in Milan when we arrived Simone checked us in
and yet Simone was waiting for us
and I was met promptly upon arrival with the keys
Cute cozy beautiful views
The apartment was perfectly located inside Montepulciano Communication was excellent
Ottima anche l'assistenza della proprietaria Speriamo di tornarci presto
This is a lovely little apartment in a perfect setting within the historic center of Montepulciano Communication with the owner was very good
The location was perfect and the price is great
l ora di tornarci proprietari professionali e molto disponibili ad ogni esigenza
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3. Holiday home with splendid views (from USD 194)

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.

Old town of Montepulciano
19 reviews
Apartment 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The beds were very comfortable
The apartment was immaculate and the beds were very comfortable with great pillows
The property was immaculate and beautiful
The Bathrooms are well appointed larger showers and plenty of hot water
The onsite parking was great and a real plus in the old city
It was beautiful clean and conveniently located
The location can't be beat
The beds were comfortable and clean
The apartment is beautifully decorated old world charm but modern touches and very clean
First of all David & Rafaella are amazing hosts
Our hosts were wonderful and so friendly and helpful
Raphella and David were so helpful and a delightful couple
Our host family were so sweet but unobtrusive
They greeted us upon arrival and set up all our dinner and lunch reservations which was so helpful
The old town section of Montepulciano where the property is located is charming with numerous restaurants and shops all within an easy walk
The location is excellent for walking to everything and right next to a beautiful park
An amazing location in a simply beautiful town
The Pileggi's were the best
This apartment is in the BEST location adjacent to a beautiful public garden with birds chirping and the corso (main street) AND Piazza Grande
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4. Apartment near Piazza Grande (from USD 139)

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.

Apartment Il Torrino
10 reviews
House 1 Bedroom 2 Bathrooms
Top guest reviews
Amenities & Room:
The view from the terrace is breathtaking
Therese is nothing to complain about
Our favorite part of the property was the sunsets from the upstairs deck breathtaking
Only one sad thing: we had to leave
The apartment was very clean and fully equipped
The host was accommodating with are arrival time
Grocery store with fresh food around the corner
we hit traffic due to snow storm and she was able to meet us at our new time
We love this apartment we have stayed before and always enjoy every minute
The 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 stay
Parking super convenient Views from upper & lower patios are panoramic & beautiful Walking anywhere in the city
Very well maintained Ideal location for getting up to the city by car
is super convenient from the house
Perfect location great view from the terrace Claudia was very helpful
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5. House with a beautiful garden (from USD 119)

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.

This splendid house in the city center with garden and wonderful views
18 reviews
villa 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
Spacious comfortable with a fully stocked kitchen and even a dining room
A car is necessary to explore Tuscany but with the included parking pass you can use this as home base
as well We will be greatful forever for the wonderful memories we have of our time in your house Paola
so you can park the car not too far away
It is well equipped and comfortable with beautiful antiques throughout
the apartment is fully equipped and was very clean
Excellent check in and check out most beautiful views in the morning and evenings
perfect location and a wonderful town boasting great wine and food a music academy museums and medieval housing
Paola is an wonderful host
The 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 restaurants
We visited Easter weekend and the town was very festive for the holiday
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 house
but if full you have to park up a steep gravel drive to a park House
it's close to everything really
Beautiful home and property Conveniently located in the city Beautiful views by day and extremely quiet at night Would definitely stay here again
The patio is great to lounge around and the view is amazing
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6. Historic dwelling with a terrace (from USD 157)

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.

La Casina Toscana- near center, independent w/ garden, wi-fi ,air cond.& parking
107 reviews
chateau / country house 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
a living/dining room
It is cozy and warm
We were driving a leased car and were please that free parking was included on site
comfortable bed and utilities are good
The other couple staying with us had to go downstairs to have their own bathroom
The place is clean as a whistle and Davide (and parents)
The place was very clean and more than adequately furnished
We found it extremely comfortable and didn't want to leave
Grazie mille per una meravigliosa vacanza
I cannot say enough about this property
He was very responsive when we needed help with a couple of requests
so he came and got us and led us to it
was a very attentive host
This property exceeded our expectations Davide was a wonderful host and the property is more beautiful than the pictures
Very well decorated Excellent maintenance Lovely outside areas (3) Wonderful and attentive host
It is in a great location for exploring the city of Montepulciano and the Tuscan area in general Walking distance to grocery stores
Location is a 10 out of 10 walk to town walk to grocery store
The bus station is within walking distance and a modern Conad grocery store
Lovely house in perfect condition just outside Montepulciano (within walking distance)
A local bus runs from the nearby bus station up to and through the city
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7. Two-bedroom residence with countryside views (from USD 112)

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.

Two bedrooms shining and fresh 140 apartment with free public parking.
58 reviews
Apartment 2 Bedrooms 2 Bathrooms

8. Spacious villa near the vineyards (from USD 259)

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.

44 reviews
House 4 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The beds were comfortable and the kitchen was stocked with everything that we needed to cook dinner in one night
the spiral staircase is a little tricky
the bedrooms had nice beds and large windows
The villa came equipped with a washing machine
The kitchen was well equipped and the house had plenty of space to relax
The villa was clean extremely spacious and offered amazing views of the countryside
There were 4 of us and the showers were hot
dishwasher refrigerator and full kitchen
The views of the deck are spectacular and Erika's home was very comfortable and clean
Also mention of water pressure which was low in the downstairs shower but adequate especially when you consider the location
Erika was such an awesome host giving us tons of helpful info before we arrived
and she was so patient and accommodating
nobody came close to her making us feel so "in the know"
Her home is gorgeous with breathtaking views
I did not know anything about the Tuscany region
Beautiful scenes and a little chilly
It is walking distance to the best restaurants and shops in Montepulciano
It is also not far from Florence and an easy drive to Pisa and Lucca
The property was conveniently located within minutes walking distance of town square Montepulciano and all the shops restaurants
The restaurants were all amazing and within a 5 - 10 minute walk away
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9. Charming family cottage

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.

apartment in a family house
21 reviews
Apartment 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
It is cozy comfortable
Very friendly owners and a well equipped apartment on the ground floor of a pleasant detached house in a quiet area of the town
Excellent apartment for convenience equipment and comfort
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 money
She even picked us up from the bus station so that we wouldn't have to walk with our luggage
She and her parents (who live upstairs) made everything seamless and easy
very clean and well-equipped
The apartment is located in a quiet neighborhood about ten walking minutes to the historic center of Montepulciano
but it only takes about 10 minutes to walk to the beginning of the historic centre
There is a bus stop a few meters from the gate
luogo molto rilassante a due passi dal centro storico di Montepulciano
There are lots of wonderful places to visit nearby if you have a car
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10. Villa with wonderful views

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.

villa with wonderful view on Montepulciano
61 reviews
Apartment 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
When researching it more and having loads of luggage
It is very spacious with a good outdoor space with excellent views of montepulciano
Great apartment with a wonderful view of Montepulciano
The only reason I can't leave a 5 star review is because of the bed in the master bedroom
then one came on automatically Very dark parking and walking to door
The apartment was clean and very charming
The apartment is spacious and very cleanThe
The property owner was very welcoming and helpful when we had to contact her to ask for information about services in the area
Spectacular Resting made easy
kitchen well equippedLoved having a walkout to the garden
Your home away from home
If the property owner would update the mattress it would be a total winner
then bus and the owner will gladly pick you up from the station if needed
it is the only way in my opinion
Many thanks to Magda and Ugo
and It's very easy to access of Montepulciano center to the another hand Owner family
Posto fantastico e proprietaria molto disponibile
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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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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