All our Vacation Rentals in Monteguidi

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

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• Sleeps   20
• Bedrooms   10
• Bathrooms   11
• Word_Label_Floor_Area   900 m²

Tuscan Hamlet Relais Piettorri

#43 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Monteguidi

from €1392per night

Private Country Resort

Nestled in the rolling hills near Siena, San Gimignano, Volterra, and Florence, Tenuta Piettorri is a beautifully restored ...

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

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

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 €580per 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

Excellent

16 Reviews

5.0

Average rating: 5.0 out of 5 based on 16 reviews

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

Luxury Villa Ripa di Galgano in Frosini

#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   12
• Bedrooms   6
• Bathrooms   6
• Word_Label_Floor_Area   400 m²

  Special Offer

Villa Elsa di Bibbiano Pool, Sauna and View

#1 Category: 5 stars out of 5

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

from €640per night

Private Villa

Overlooking the rolling vineyards of Colle di Val d’Elsa from a panoramic promontory, Villa d’Elsa brings together a deep ...

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

Excellent

23 Reviews

5.0

Average rating: 5.0 out of 5 based on 23 reviews

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• Sleeps   12
• Bedrooms   6
• Bathrooms   6
• Word_Label_Floor_Area   900 m²

Poggiarelllo Apartments in Medieval Castle: Rustic Tuscan Charm

#38 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Sovicille

from €1160per 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

5 Reviews

4.8

Average rating: 4.8 out of 5 based on 5 reviews

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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 €325per 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

Excellent

6 Reviews

5.0

Average rating: 5.0 out of 5 based on 6 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 €189per 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

19 Reviews

5.0

Average rating: 5.0 out of 5 based on 19 reviews

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

Capanna al Lago, Chianti Heritage with Vineyards View

#5 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €320per 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

18 Reviews

5.0

Average rating: 5.0 out of 5 based on 18 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

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   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

43 Reviews

5.0

Average rating: 5.0 out of 5 based on 43 reviews

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

La Piazza Grand Vista Apartments

#41 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €400per 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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La Piazza Il Campo Apartment

#1

Sleeps   2 Bedrooms   1 Bathrooms   1 Floor Area   120 m²

from €400per night

Grand Terrace Apartment

#2

Sleeps   2 Bedrooms   1 Bathrooms   1 Floor Area   120 m²

from €400per night

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• Sleeps   4
• Bedrooms   2
• Bathrooms   2

La Piazza Grand Terrace Villa

#42 Category: 5 stars out of 5

1. Italy
2. Tuscany
3. Siena

from €760per night

Private City / Village Apartment

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

• Internet
• In Village
• Internet Wifi
• Business
• Stone Building
• Panoramic View City

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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 €287per 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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• 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 €267per 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

12 Reviews

5.0

Average rating: 5.0 out of 5 based on 12 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 €598per 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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