
Holiday rentals in Montepulciano
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Top-rated holiday rentals in Montepulciano
Guests agree: these stays are highly rated for location, cleanliness and more.

A generous space between ancient and modern in the center of Montepulciano
Let yourself be enveloped by the feeling of intimacy and warmth of this large space where the various areas are divided by original solutions. Original features, such as exposed beams, are associated with fresh and contemporary elements. A bright environment ideal for 2 people but can comfortably accommodate 3 (armchair bed). The kitchen of the house is equipped with all the services for the exclusive use of this room: a dining table, TV, wifi, and a private bathroom with a shower. Guests have access to the common entrance area of the ManillaHouse and the Hexagon room. Security lock closure. Guests can contact me if they need to. In any case, the house is well organized and equipped with information sheets to resolve the usual minor technical issues. Within walking distance are restaurants, bars, shops and various services. In the summer, various events are organized such as the International Art Festival, while in the winter the country is embellished with the lights and colors of the Christmas markets. It is located in the ZTL, the car can be parked in the public parking lots P6 P7 P8, perimeter to the center of the village in the upper part and within walking distance from the accommodation. For trips further afield, there is an urban public transport line called "Pollicino" that connects the historic center to the newer part of the town. Montepulciano can be reached by car from the A1 Val di Chiana and A1 Chiusi-Chianciano Terme motorway exits (Parking near home no. 6-7-8), by train from Chiusi Chianciano Terme station, by bus from Siena, Rome and Florence. While staying, you may hear music from the nearby Montepulciano Music Institute, violins, pianos, trumpets and beautiful singing could be the background of your stay, but should not cause disturbance.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Tuscan cottage with an heavenly view
Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Stuart Black Tea Amazing View & Super Central
This apartment is in a prime central location and enhanced by an abundance of natural light and awe-inspiring panoramic vistas. It features one double bedroom, a panoramic living room, a bathroom with shower, and a spacious kitchen. Its advantageous proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. Additionally, guests will have access to a backyard garden, creating an ideal setting for savouring a glass of wine

Montepulciano Historic Center
Nice 60-square-meter apartment located on the main street of the town. It is located on the second and top floor of a historic building. The entrance is located on the main street of the town while the windows face the outside of the walls offering a breathtaking view. The apartment consists of: an entrance, a living room with a double sofa bed, a bedroom, a kitchen, and a bathroom with a roof window. It is equipped with a microwave, large oven, dishwasher, washing machine and wifi.
La Piazzetta - Cozy open space in the historic center of Montepulciano
Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Then go outside and admire the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, and stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana Valley.

"Dimora Valinda" Montepulciano Piazza Grande + A/C
Welcome to Montepulciano, a historical gem! Our apartment, located in the heart of the historic center, offers the perfect location to experience the authenticity of this unique place: just a few steps from Piazza Grande, excellent restaurants, shops, and all the main attractions. Whether you come to explore the wineries, for a romantic getaway, or to learn about the history and culture of Montepulciano, here you will find the perfect place for an unforgettable experience.

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Casa Bonari - a paradise for the eyes
Casa Bonari is a single-level independent apartment inside a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, an equipped kitchen and a living room. The rooms are bright and furnished in Tuscan style, with old restored family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on all sides by a large garden, so that all rooms boast a beautiful view of the countryside.

I Tramonti di Eramo, Montepulciano city center.
Welcome to Montepulciano, the jewel of the Tuscan hills! Our apartment in the heart of the historic center offers breathtaking views of the surrounding countryside, providing an authentic and unforgettable experience. Step outside and savor the historic atmosphere of Montepulciano. Just a few steps away, you will find the extraordinary Piazza Grande, excellent restaurants, and all kinds of services. Tuscany awaits you for a unique experience.

Casale Santa Barbara - Exclusive Apartment
Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.
Popular amenities for Montepulciano holiday rentals
Other great holiday rentals in Montepulciano

Casa Tòrta - comfort room

a.d. 1237

Casa di Mela

"Hortus Conclusus" House

Mery's House: elegant apartment

the birds view

Panoramic view & outdoor jacuzzi - Pienza

La finestra - Montepulciano's historic center
When is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $143 SGD | $139 SGD | $145 SGD | $159 SGD | $168 SGD | $172 SGD | $169 SGD | $179 SGD | $183 SGD | $175 SGD | $163 SGD | $175 SGD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Frequently Asked Questions
What are the best places to stay in Montepulciano?
Montepulciano has stays in its historic center, near medieval squares, and around scenic countryside with vineyard views. Travelers often choose homes tucked along centuries-old streets or rural estates surrounded by vineyards.
What are the best things to do in Montepulciano with kids?
Families can explore Montepulciano's fortress, climb medieval towers, and discover interactive exhibits in local museums. Many enjoy tasting local treats or joining relaxed countryside walks near the town.
What are some of the best things to do in Montepulciano?
Explore historic squares such as Piazza Grande, tour local wineries, and visit underground cellars. Montepulciano has walking routes through medieval alleys, and the Fortezza Medicea is often recommended for panoramic views.
How is the weather in Montepulciano?
Montepulciano experiences mild winters between 33–49°F (0–9°C), and warm, dry summers near 60–89°F (16–32°C). Spring and autumn bring more rainfall alongside comfortable temperatures.
When is the best time to visit Montepulciano?
Late spring and early autumn are often suggested for milder weather and colorful scenery. Summer draws visitors for festivals and outdoor dining, while winter has a quieter pace and festive events.
What are the best places to visit in Montepulciano?
Montepulciano has frequently suggested sites like the Piazza Grande, the town’s cathedral, and Fortezza Medicea. Exploring local wineries and artisan shops provides deeper connections to the area’s culture.
What are some hiking trails in Montepulciano?
Visitors can explore trails winding across vineyards, forested hills, and olive groves near Montepulciano. Walking paths often lead to panoramic viewpoints and quiet countryside with chances to spot local wildlife.
What are some family activities we can do in Montepulciano?
Families enjoy roaming Montepulciano’s historic alleys, joining guided walks, and tasting local gelato from cafés. Nearby farms sometimes have kid-friendly tours, and interactive museum exhibits welcome curious learners.
What are some of the best day trip ideas from Montepulciano?
Day trips frequently suggested near Montepulciano include visiting hilltop villages, thermal baths, and regional nature parks. Many travelers explore Renaissance towns known for art, culture, and scenic landscapes.
Are there any pet friendly accommodations available in Montepulciano?
Montepulciano has pet friendly stays in central neighborhoods and countryside areas. Many hosts welcome guests traveling with pets, and some locations feature outdoor spaces for walking and relaxing together.
What are some local tips for visiting Montepulciano?
Wear comfortable shoes for cobbled streets, and bring a light jacket in spring or autumn. Locals often suggest sampling Vino Nobile and exploring markets for regional foods and crafts.
What is Montepulciano known for?
Montepulciano is known for its Renaissance architecture, winding medieval streets, and the production of Vino Nobile red wine. The town’s hilltop location has panoramic countryside views and lively wine traditions.
What are the best hidden gems to explore in Montepulciano?
Visitors often discover artisan workshops tucked into side streets, quiet courtyards behind historic buildings, and underground wine cellars carved from stone. Small churches and less-frequented gardens around town highlight Montepulciano’s historic layers.
What are the best foods to try in Montepulciano?
Montepulciano has locally rooted dishes like pici pasta, Tuscan pecorino cheese, and cured meats. Pairings with Vino Nobile wine and seasonal specialties such as wild boar are frequently suggested.
What should I bring for a trip to Montepulciano?
Pack comfortable walking shoes, layered clothing for changing temperatures, and a reusable water bottle. If traveling in spring or autumn, a waterproof jacket may come in handy for unexpected rain.
What is the nightlife in Montepulciano like?
Montepulciano’s nightlife often centers on wine bars, cozy taverns, and casual cafés where locals and visitors gather. Some venues host live music, tasting events, or feature regional wines in relaxed settings.
What are the most popular events or festivals in Montepulciano?
Montepulciano has the Bravio delle Botti barrel-rolling competition in late summer, wine festivals celebrating Vino Nobile, and seasonal markets in historic squares. Medieval reenactments and holiday fairs are also popular traditions.
Are there family friendly vacation rentals in Montepulciano?
Many vacation rentals in Montepulciano welcome families, with homes near central squares and more spacious countryside stays. Options often include kitchens and private outdoor spaces for a relaxed visit.
Quick stats about holiday rentals in Montepulciano

Total holiday rentals
Explore 300 holiday rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $50 SGD per night before taxes and fees

Verified guest reviews
Over 17,400 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
300 of Montepulciano holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Montepulciano rentals

4.9 Average rating
Montepulciano stays are highly rated by guests – averaging 4.9 out of 5!
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- Lake Trasimeno
- Del Chianti
- Lake Bolsena
- Eremo Di Camaldoli
- Siena Cathedral
- Cascate del Mulino
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Mount Subasio
- Palazzo Pubblico
- Santa Maria della Scala
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Antinori nel Chianti Classico
- Rocca Maggiore
- Saturnia Thermal Park
- Pozzo di San Patrizio
- Castello di Verrazzano
- Vulci
- Abbey of Sant'Antimo
- Val di Chiana
- Abbazia di San Galgano
- Parco Regionale Della Maremma
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