All our Vacation Rentals in Montepulciano

Explore handpicked villas & apartments in Montepulciano, Tuscany. Authentic local stays, personalized service, unforgettable Italian memories.

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• Sleeps   10
• Bedrooms   5
• Bathrooms   6

Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia

#24 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Montepulciano

from €2000per night

Private Villa

Set in an elevated position above rolling vineyards, Villa Petrosa opens onto wide, uninterrupted views across the stunning ...

• Garden
• Near Village
• Baby Bed
• Parking
• Swimming Pool
• Our Suggestion

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• Sleeps   14
• Bedrooms   7
• Bathrooms   7

Villa San Biagio

#21 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Montepulciano

from €620per night

Private Villa

A panoramic hillside villa within walking distance of Montepulciano Set on a quiet hillside just outside Montepulciano, Villa ...

• Garden
• Near Village
• Baby Bed
• Parking
• Bike
• Swimming Pool

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• Sleeps   12
• Bedrooms   6
• Bathrooms   4
• Word_Label_Floor_Area   300 m²

Dimora Di Castroncello

#6 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Castroncello

from €535per night

Private Villa

A private, indipendent villa in the Val di Chiana, shaped by genuine Tuscan hospitality Set in the green landscape of the Val di ...

• Garden
• Near Village
• Baby Bed
• Parking
• Swimming Pool
• Weddings

Excellent

1 Reviews

5.0

Average rating: 5.0 out of 5 based on 1 reviews

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• Sleeps   8
• Bedrooms   4
• Bathrooms   4
• Word_Label_Floor_Area   250 m²

Villa Marielena Chianti Farmhouse with Hot Tub

#22 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Castell'in Villa

from €309per night

Private Villa

Nestled in the prestigious "Castel in Villa" area of Gaiole in Chianti, Villa Marielena is a beautifully luxury restored ...

• Garden
• Near Village
• Baby Bed
• Parking
• Our Suggestion
• Internet Wifi

Excellent

9 Reviews

5.0

Average rating: 5.0 out of 5 based on 9 reviews

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• Sleeps   6
• Bedrooms   3
• Bathrooms   3
• Word_Label_Floor_Area   200 m²

  Special Offer

Capanna al Lago, Chianti Heritage with Vineyards View

#5 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €252per night

Private Villa

Capanna al Lago is a charming private villa set on a gentle hillside overlooking the rolling landscapes of Chianti. Surrounded ...

• Garden
• Near Village
• Internet
• Baby Bed
• Parking
• Swimming Pool

Excellent

14 Reviews

5.0

Average rating: 5.0 out of 5 based on 14 reviews

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• Sleeps   11
• Bedrooms   6
• Bathrooms   6
• Word_Label_Floor_Area   400 m²

  Special Offer

Villa del Mangia - Luxury Villa with Infinity Pool & Breathtaking Views of Siena

#14 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €1949per night

Private Villa

Experience the ultimate Tuscan escape at Villa del Mangia, a stunning, fully renovated luxury villa rental near Siena. Seamlessly ...

• Garden
• Near Village
• Baby Bed
• Parking
• Swimming Pool
• Weddings

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• Accommodation   2
• Sleeps   4
• Bedrooms   2
• Bathrooms   2

La Piazza Grand Vista Suite

#41 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €630per night

City / Village Apartment

In the heart of Siena, above the world’s most beautiful square, sits a fully renovated luxury historic home. Two independent or ...

• Internet
• Next Year Available
• Chef
• Our Suggestion
• Internet Wifi
• Business

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Il Campo Grand Terrace Suite

#1

Sleeps   2 Bedrooms   1 Bathrooms   1 Floor Area   120 m²

from €630per night

Grand Vista Suite Terrace

#2

Sleeps   2 Bedrooms   1 Bathrooms   1 Floor Area   120 m²

from €630per night

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• Sleeps   8
• Bedrooms   4
• Bathrooms   4
• Word_Label_Floor_Area   180 m²

  Special Offer

Capanna di Elfo

#4 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €448per night

Private Villa

Capanna di Elfo is a beautifully restored former Tuscan barn, carefully renovated by its owners Claudio and Angelica to create a ...

• Garden
• Internet
• Baby Bed
• Parking
• Next Year Available
• Our Suggestion

Excellent

33 Reviews

5.0

Average rating: 5.0 out of 5 based on 33 reviews

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• Sleeps   8
• Bedrooms   4
• Bathrooms   3
• Word_Label_Floor_Area   200 m²

Casamia Sky-High Panoramic Retreat: Penthouse with Easy Parking, 4Br

#3 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €172per night

City / Village Apartment

Experience a family legacy! Reimagined by the owner Francesca (an architect), this 200sqm sky-high retreat was originally ...

• Near Village
• Internet
• Baby Bed
• Parking
• In Village
• Next Year Available

Excellent

15 Reviews

5.0

Average rating: 5.0 out of 5 based on 15 reviews

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• Sleeps   8
• Bedrooms   4
• Bathrooms   5
• Word_Label_Floor_Area   200 m²

Dimora Chianti Shire: Stunning Tuscan Villa on Vineyards with Private Pool

#13 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Rietine

from €632per night

Private Villa

Set among rolling vineyards and olive groves, this restored stone villa offers complete privacy in one of the most iconic ...

• Garden
• Baby Bed
• Parking
• Swimming Pool
• Our Suggestion
• Internet Wifi

Excellent

1 Reviews

5.0

Average rating: 5.0 out of 5 based on 1 reviews

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• Sleeps   6
• Bedrooms   3
• Bathrooms   3
• Word_Label_Floor_Area   200 m²

San Sano Retreat, Chianti Vineyard Views & Diving

#40 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. San Sano

from €286per night

Private Villa

Tucked away on the edge of the postcard-worthy village of San Sano, you'll get ultimate peace and quiet alongside jaw-dropping ...

• Garden
• Near Village
• Internet
• Parking
• Swimming Pool
• Weddings

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