All our Vacation Rentals in Monteriggioni

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

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

  Special Offer

Podere Lorena, 13Th-Century Farmhouse in the Montagnola Senese

#7 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Monteriggioni

from €330per night

Private Country House / Farm House

Set within the protected woodland of the Montagnola Senese, this restored 13th-century farmhouse offers a stay immersed in ...

• Garden
• Internet
• Baby Bed
• Parking
• Swimming Pool
• Chef

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• Sleeps   14
• Bedrooms   7
• Bathrooms   6
• Word_Label_Floor_Area   350 m²

Villa L'elsa Beautiful Country Home With View

#1 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Colle Di Val D’elsa

from €534per night

Private Villa

Perched on a panoramic promontory overlooking the rolling vineyards of Colle di Val d’Elsa, Villa d’Elsa is where ancient ...

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

Excellent

2 Reviews

5.0

Average rating: 5.0 out of 5 based on 2 reviews

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• Sleeps   14
• Bedrooms   7
• Bathrooms   6
• Word_Label_Floor_Area   450 m²

  Special Offer

Casale del Timignano, Private Villa with Huge Garden and Pool

#10 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Le Grazie

from €563per night

Private Villa

A Story of Love, Family, and Tuscan Soul: Spread over two spacious levels, the villa comfortably hosts up to 14 guests — ideal ...

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

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

Capanna Di Elfo

#4 Category: 4 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €474per 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

7 Reviews

5.0

Average rating: 5.0 out of 5 based on 7 reviews

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

Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking

#3 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €266per 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

2 Reviews

5.0

Average rating: 5.0 out of 5 based on 2 reviews

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

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

#14 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €1958per 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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• Sleeps   6
• Bedrooms   3
• Bathrooms   3
• Word_Label_Floor_Area   200 m²

  Special Offer

Capanna Al Lago

#5 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €390per night

Private Villa

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

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

Excellent

5 Reviews

5.0

Average rating: 5.0 out of 5 based on 5 reviews

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• Sleeps   4
• Bedrooms   2
• Bathrooms   2
• Word_Label_Floor_Area   90 m²

The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo

#8 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €195per night

Private City / Village Apartment

Experience the luxury of silence in the heart of Siena. Tucked behind an exclusive private courtyard, this sanctuary offers a ...

• In Village
• Internet Wifi
• Baby Crib
• Fridge
• Washing Machine
• Dishwasher

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• Sleeps   12
• Bedrooms   6
• Bathrooms   6
• Word_Label_Floor_Area   800 m²

  Special Offer

Medieval Castle Living: Vineyards, Swimming Pool & Rustic Tuscan Charm

#38 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Sovicille

from €1162per night

Private Castle Apartment

Step back in time and live the "Castle's Life" at our family’s private estate. Enclosed by ancient medieval walls just 15 ...

• Garden
• Internet
• Parking
• Bike
• 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   5
• Word_Label_Floor_Area   200 m²

La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti

#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

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

Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience

#22 Category: 5 stars out of 5

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

from €342per 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

1 Reviews

5.0

Average rating: 5.0 out of 5 based on 1 reviews

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• Sleeps   12
• Bedrooms   6
• Bathrooms   7
• Word_Label_Floor_Area   650 m²

Luxury Villa Ripa Di Galgano

#37 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Frosini

from €2228per night

Private Villa

Settled in a strategic position, yet conveniently located—just a 10-minute drive from everything (with the charming village of ...

• Garden
• Near Village
• Internet
• Maid Service
• Parking
• Bike

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• Sleeps   4
• Bedrooms   2
• Bathrooms   3
• Word_Label_Floor_Area   300 m²

Elegant Suite: Florence Apartment with View on Medici Chapels

#26 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Florence

from €714per night

Private City / Village Apartment

Magnificent historic residence 300 sqm, situated in the heart of Florence, just behind the Basilica of San Lorenzo, with ...

• Internet
• In Village
• Internet Wifi
• Business
• Panoramic View City
• Baby Crib

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