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Vacation rentals in Montepulciano

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Top-rated vacation rentals in Montepulciano

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Top guest favorite
A bright kitchen area with wooden beams overhead features a dining table set for four. Wall shelves display dishes and glassware, while a modern stove is positioned against a decorative tiled backsplash. Natural light enters through a partially open window, enhancing the inviting space.
Apartment in Montepulciano
4.97 out of 5 average rating, 376 reviews

Ampio spazio tra antico e moderno nel centro di Montepulciano

Fatti avvolgere dalla sensazione di intimità e calore di questo ampio spazio dove le varie zone sono suddivise da soluzioni originali. Le caratteristiche originali, come le travi a vista, sono associate a elementi freschi e contemporanei. Ambiente luminoso ideale per 2 persone ma può ospitarne tranquillamente 3 (poltrona letto). Cucina della casa dotata di tutti i servizi ad uso esclusivo di questa camera, tavolo da pranzo, tv, wi-fi e bagno privato con doccia. Gli Ospiti hanno accesso alla zona comune d'ingresso della ManillaHouse e alla camera Esagona. Chiusura di sicurezza con serratura. In caso di bisogno gli Ospiti mi possono contattare. In ogni caso la casa è ben organizzata e corredata di fogli informativi per risolvere piccoli problemi tecnici ordinari. A pochi passi si trovano ristoranti, bar negozi e vari servizi. In estate vengono organizzati vari eventi quali il Festival Cantiere Internazionale d'Arte, mentre in inverno il paese si abbellisce delle luci e dei colori dei mercatini natalizi. Si trova in ZTL, la macchina si può parcheggiare nei parcheggi pubblici P6 P7 P8 , perimetrali al centro del paese nella parte alta e poco distanti a piedi dall'alloggio. Per gli spostamenti più lontani c'è una linea di trasporto pubblico urbano denominata "Pollicino" che collega il centro storico alla zona più recente del paese. Montepulciano è raggiungibile in auto dalle uscite autostradali A1 Val di Chiana e A1 Chiusi-Chianciano Terme (Parcheggi vicini a casa n.6-7-8), in treno dalla stazione di Chiusi Chianciano Terme, in autobus da Siena, Roma e Firenze. Può capitare soggiornandovi di sentire della musica proveniente dal vicino Istituto Musicale di Montepulciano, violini, pianoforti, trombe e bel canto potrebbero essere il sottofondo del vostro soggiorno ma senza arrecare disturbo.

Top guest favorite
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.
Guesthouse in Macciano
4.97 out of 5 average rating, 207 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 favorite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 140 reviews

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

Guest favorite
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
4.92 out of 5 average rating, 284 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 favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Guest favorite
A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.
Apartment in Montepulciano
4.97 out of 5 average rating, 148 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 favorite
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, 487 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.

Guest favorite
A private terrace is visible, adorned with vibrant flowers and a small table set for two. A bottle of wine and two glasses are elegantly placed, inviting relaxation with a view of the terracotta rooftops and the distant landscape under a pastel sky.
Condo in Montepulciano
4.93 out of 5 average rating, 160 reviews

"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.

Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza
5 out of 5 average rating, 138 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Top guest favorite
A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.
Apartment in Montepulciano
4.93 out of 5 average rating, 263 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 favorite
A terracotta-tiled terrace overlooks rolling hills, adorned with potted plants and a decorative wall. Wooden loungers provide seating, while a small table is positioned under a large tree, offering a shaded spot to enjoy the scenic views of the surrounding landscape.
Condo in Montepulciano
4.88 out of 5 average rating, 104 reviews

Vicolo delle Mura, ancient home with a view

Our old family home is in a quiet and secluded location in the historic center of Montepulciano. It has a beautiful and large habitable terrace overlooking the Valdichiana. Its central location allows you to walk to Piazza Grande, the Pulcinella Tower, the Medici Fortress and the San Biagio Rectory. Nearby you will find a wide selection of businesses and restaurants where you can enjoy delicious Tuscan cuisine.

Top guest favorite
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.
Apartment in Montepulciano
5 out of 5 average rating, 105 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.

Popular amenities for Montepulciano vacation rentals

When is the best time to visit Montepulciano?

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Avg. priceﺩ.ﺇ415ﺩ.ﺇ404ﺩ.ﺇ422ﺩ.ﺇ463ﺩ.ﺇ488ﺩ.ﺇ499ﺩ.ﺇ492ﺩ.ﺇ521ﺩ.ﺇ533ﺩ.ﺇ510ﺩ.ﺇ474ﺩ.ﺇ510
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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 vacation rentals in Montepulciano

  • Total vacation rentals

    Explore 300 vacation rentals in Montepulciano

  • Nightly prices starting at

    Montepulciano vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 17,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Montepulciano vacation rentals include wi-fi 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