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All our Vacation Rentals in Montepulciano

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

Results 1 - 12 of 12
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
Villa Petrosa: Your Private Escape Overlooking the Val D'Orcia
  •   10
  •   5
  •   6
from €2000per night
Private Villa
A hidden gem nestled in the heart of our estate, where the charm of the Tuscan countryside meets the timeless beauty of ...
  • Garden
  • Near Village
  • Baby Bed
  • Parking
  • Swimming Pool
  • Our Suggestion
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
Villa Cortona: Eco-Sustainable Luxury Estate with Private Spa & Gym
  •   14
  •   6
  •   6
  •   600 m2
  Special Offer
from €1399per night
Private Villa
Villa Cortona is a beautiful newly restored villa with annexe and private swimming pool, spa,jacuzzi and gym situated in a ...
  • Garden
  • Near Village
  • Baby Bed
  • Parking
  • Swimming Pool
  • Weddings
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
Marielena Authentic Chianti Retreat: Panoramic Views & Private Hot Tub for a Chianti Lifestyle Experience
  •   8
  •   4
  •   4
  •   250 m2
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
Capanna Di Elfo: Autumn, Building Exterior, Garden, Outdoor, Scenic View, Spring, Summer
Capanna Di Elfo: Autumn, Garden, Hot Tub, Outdoor, Scenic View, Spring, Summer
Capanna Di Elfo: Autumn, Balcony / Terrace / Patio, Building Exterior, Garden, Outdoor, Spring, Summer
Capanna Di Elfo: Autumn, Living Room, Spring, Summer
Capanna Di Elfo: Autumn, Living Room, Spring, Summer
Capanna Di Elfo: Autumn, Building Exterior, Garden, Outdoor, Spring, Summer
Capanna Di Elfo
Capanna Di Elfo: Autumn, Building Exterior, Outdoor, Spring, Summer
Capanna Di Elfo: Autumn, Dining Room, Spring, Summer
Capanna Di Elfo: Autumn, Living Room, Spring, Summer
Capanna Di Elfo: Autumn, Garden, Main Entrance, Outdoor, Scenic View, Spring, Summer
Capanna Di Elfo: Autumn, Hot Tub, Outdoor, Spring, Summer
Capanna Di Elfo: Autumn, Building Exterior, Garden, Outdoor, Spring, Summer
Capanna Di Elfo: Autumn, Living Room, Spring, Summer
Capanna Di Elfo: Autumn, Living Room, Spring, Summer
Capanna Di Elfo: Autumn, Building Exterior, Garden, Outdoor, Spring, Summer
Capanna Di Elfo: Autumn, Building Exterior, Garden, Spring, Summer
Capanna Di Elfo: Autumn, Building Exterior, Garden, Main Entrance, Scenic View, Spring, Summer
Capanna Di Elfo: Autumn, Dining Room, Spring, Summer
Capanna Di Elfo: Autumn, Dining Room, Kitchen, Spring, Summer
  •   8
  •   4
  •   4
  •   180 m2

#4
  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
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, City, Outdoor, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, Outdoor, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Hot Tub, Outdoor, Scenic View, Spring, Summer, Wellness, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Dining Room, Living Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Amenities, Autumn, Facilities, Living Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Balcony / Terrace / Patio
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, Outdoor, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Outdoor, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Living Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Dining Room, Living Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Building Exterior, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, Outdoor, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Dining Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Amenities, Autumn, Living Room, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Outdoor, Scenic View, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, Hot Tub, Outdoor, Scenic View, Spring, Summer, Wellness, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Balcony / Terrace / Patio, Building Exterior, Hot Tub, Outdoor, Planimetry, Scenic View, Spring, Summer, Wellness, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Amenities, Autumn, Dining Room, Facilities, Spring, Summer, Winter
Casamia Tuscan Oasis: 4Br Panoramic Penthouse, Sky-High Retreat with Private Hot Tub & Easy Parking: Autumn, Dining Room, Spring, Summer, Winter
  •   8
  •   4
  •   3
  •   200 m2
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
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
Luxury Villa with Infinity Pool & Breathtaking Views of Siena – Villa del Mangia
  •   11
  •   6
  •   6
  •   400 m2
  Special Offer
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
Capanna Al Lago: Autumn, Garden, Pool, Scenic View, Spring, Summer, Winter
Capanna Al Lago: Autumn, Balcony / Terrace / Patio, Building Exterior, Garden, Scenic View, Spring, Summer, Winter
Capanna Al Lago: Autumn, Building Exterior, Garden, Spring, Summer, Winter
Capanna Al Lago
Capanna Al Lago
Capanna Al Lago: Autumn, Garden, Hot Tub, Scenic View, Spring, Summer, Winter
Capanna Al Lago: Autumn, Pool, Scenic View, Spring, Summer, Winter
Capanna Al Lago: Autumn, Building Exterior, Garden, Spring, Summer, Winter
Capanna Al Lago
Capanna Al Lago
Capanna Al Lago: Autumn, Building Exterior, Spring, Summer, Winter
Capanna Al Lago: Autumn, Pool, Scenic View, Spring, Summer, Winter
Capanna Al Lago: Autumn, Building Exterior, Garden, Spring, Summer, Winter
Capanna Al Lago
Capanna Al Lago
Capanna Al Lago: Autumn, Pool, Spring, Summer, Winter
Capanna Al Lago: Autumn, Building Exterior, Spring, Summer, Winter
Capanna Al Lago: Autumn, Pool, Spring, Summer, Winter
Capanna Al Lago
Capanna Al Lago
  •   6
  •   3
  •   3
  •   200 m2
  Special Offer

#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
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
The Silent Courtyard Retreat: Spacious 2-Bedroom Sanctuary Steps from Piazza del Campo
  •   4
  •   2
  •   2
  •   90 m2
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
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
La Dimora del Chianti Dimora: Stunning Tuscan Stone Villa Surrounded by Vineyards in the Heart of Chianti
  •   8
  •   4
  •   5
  •   200 m2
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