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Holiday rentals in Montepulciano

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Montepulciano

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Asciano
4.96 out of 5 average rating, 130 reviews

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.

Top guest favourite
A charming terrace features a small round table and two white chairs, offering expansive views of the surrounding hills and distant landscape. A walnut tree stands nearby, enhancing the tranquil outdoor space bathed in natural light from the setting sun.
Apartment in Montepulciano
5 out of 5 average rating, 109 reviews

The walnut tree view, Montepulciano

The walnut tree view ( castoldi apartments site) is our new apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 1 double rooms (king ) 1 bathroom with large shower and a large kitchen-living room with a nice terrace overlooking the hills. From summer 26 a wine tasting will be available in the new garden for all the guests from 7 pm Old private wine cellar available Guests will park close the apartment

Top guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guest house in Macciano
4.97 out of 5 average rating, 221 reviews

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.

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 300 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
Flat in Montepulciano
4.97 out of 5 average rating, 159 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Top guest favourite
A wooden table is set with two cream-colored cups and a small vase filled with dried wheat and decorative grasses. The white brick wall creates a warm backdrop, enhancing the inviting atmosphere of the dining area.
Flat in Montepulciano
4.99 out of 5 average rating, 290 reviews

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.

Top guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 499 reviews

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.

Superhost
A round dining table is set on a terrace, surrounded by woven chairs. A colorful yellow vase filled with pink flowers is at the center. The view reveals rolling hills and a clear sky, providing a serene backdrop to outdoor dining.
Flat in Montepulciano
4.82 out of 5 average rating, 113 reviews

Casa Evelina - Incredible View, Central Location

Benvenuti nel cuore del centro storico di Montepulciano. Questa casa esclusiva unisce spazio, comfort e un’autenticità rara: un luogo ideale per famiglie, gruppi di amici o ospiti in cerca di un soggiorno memorabile in una delle città più affascinanti della Toscana. Qui potrete vivere Montepulciano da una prospettiva privilegiata: uscire di casa e trovarvi immediatamente immersi tra palazzi rinascimentali, botteghe artigiane, cantine storiche e ristoranti tipici.

Guest favourite
A wooden balcony table is set for tea, featuring delicate china cups accompanied by cookies. A simple vase holds fresh flowers. The stunning countryside view stretches across rolling hills under a clear sky, enhancing the serene atmosphere of the outdoor space.
Flat in Montepulciano
4.92 out of 5 average rating, 277 reviews

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.

Top guest favourite
An outdoor terrace is presented with a modern seating arrangement featuring two white cushioned chairs and a matching sofa surrounding a dark coffee table. The view captures the rooftops of Montepulciano, complemented by a clear blue sky and distant hills.
Flat in Montepulciano
5 out of 5 average rating, 113 reviews

Dimora dell'Erbe - Rooftop Apartment

The apartment has two independent double bedrooms with private bathroom (Nepitella and Timo), a large bright kitchen with living room and finally exclusive access to the beautiful terraces that overlook the roofs of Montepulciano. The modern and functional kitchen offers an induction hob, dishwasher fridge and a service for 6 people. Independent air conditioning and heating and wi-fi.

Top guest favourite
Home in Monticchiello
4.98 out of 5 average rating, 209 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Guest favourite
A rustic dining area features a spacious table set with plates and glassware, surrounded by wooden chairs. Exposed beams highlight the ceiling, while a soft lamp provides gentle illumination. A glimpse of the outside view can be seen through the window, enhancing the inviting atmosphere.
Flat in Montepulciano
4.9 out of 5 average rating, 215 reviews

Tuscany on the terrace, downtown Montepulciano

Welcome to Montepulciano, the hidden gem of Tuscany, where historical charm blends harmoniously with natural beauty. Our Airbnb in the heart of the historic center embodies the elegance and authenticity of this region.

Popular amenities for Montepulciano holiday rentals

When is the best time to visit Montepulciano?

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Avg. price$167 SGD$163 SGD$169 SGD$161 SGD$170 SGD$174 SGD$171 SGD$181 SGD$185 SGD$177 SGD$165 SGD$177 SGD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°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 310 holiday rentals in Montepulciano

  • Nightly prices starting at

    Montepulciano holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 17,300 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

  • Wifi availability

    300 of Montepulciano holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montepulciano rentals

  • 4.9 Average rating

    Montepulciano stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Montepulciano