
Holiday rentals in Montepulciano
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Top-rated holiday rentals in Montepulciano
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Palazzo Monaci - Piscina nelle crete Senesi
Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

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

L'Aquila e L'Ulivo
All'Aquila e l'Ulivo, un antico casale ristrutturato del 1200, troverai non solo tutti i confort necessari per uno splendido soggiorno, ma vivrai anche l'emozione di sentirti libero e immerso nella natura incontaminata della Val D'Orcia. Qui avrai la possibilita' di passeggiare con i due falchi Ayga e Sayen e interagire con le aquile, e perchè non sorseggiare un eccellente aperitivo a bordo piscina. Ti aspettiamo nel nostro mondo, fatto di animali, relax, natura e anche un pizzico di Magia.

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

Casa Bonari - un paradiso per gli occhi
Casa Bonari è un appartamento indipendente su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina attrezzata e salotto. Le stanze sono luminose e arredate in stile toscano, con vecchi mobili di famiglia ristrutturati uniti ad elementi contemporanei. La cucina è completamente attrezzata e l'appartamento circondato su ogni lato da un grande giardino, così che tutte le stanze vantano un bellissimo panorama sulla campagna.
La Piazzetta -Accogliente open space nel centro storico di Montepulciano
Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla 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, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

A paradise in Montepulciano...
Villa Il Cubo has a large private park and swimming pool and marvellous views on the Tuscan countryside. It is fully air-conditioned and the decoration has been updated with charming details that will make you enjoy the best Tuscany has to offer. We have electric vehicle charging point at a moderate extra contribution. Supermarkets, restaurants, grocery stores, wineries are just a few minutes away. IN JULY AND AUGUST LET FOR A MINIMUM OF 7 DAYS FROM SATURDAY TO SATURDAY.

Podere Pereti Nuovi-modern Tuscan Villa
Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

I Tramonti di Eramo , Montepulciano centro.
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.

Casa Ricci Appartamento in palazzo del 1300
Il nostro appartamento è situato a pochi metri da Piazza Grande,può ospitare fino a 4 persone e si affaccia su un panorama suggestivo .E stato recentemente ristrutturato e si trova in un edificio storico del 1300. Our apartment is located a few meters from Piazza Grande, it sleeps up to 4 people and overlooks a beautiful. Was recently renovated and is located in a historic building in 1300.

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

a.d. 1237

Luxury New Stay with Private Patio in Old Town

Wine Loft tra le vigne

Borgo 7 Tigli | Family stay with garden & pool

the birds view

Elegant farmhouse overlooking Pienza

Unique view 3 bdr villa with pool & A/C in Pienza

La finestra - centro storico Montepulciano
When is the best time to visit Montepulciano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $144 SGD | $140 SGD | $146 SGD | $160 SGD | $169 SGD | $173 SGD | $170 SGD | $180 SGD | $184 SGD | $177 SGD | $164 SGD | $177 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 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!
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- Lake Trasimeno
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- Eremo Di Camaldoli
- Basilica of St Francis
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Palazzo Pubblico
- Mount Subasio
- Santa Maria della Scala
- Ugolino Golf Club
- Rocca Maggiore
- Castello di Verrazzano
- Antinori nel Chianti Classico
- Siena Cathedral
- Parco Regionale Della Maremma
- Abbey of Monte Oliveto Maggiore
- Cathedral of San Lorenzo
- Saturnia Thermal Park
- La Scarzuola
- Val di Chiana
- Giardini del Frontone
- Cappella di Vitaleta
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