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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 €2571per 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
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
from €1399per night
Private Villa
Villa Cortona masters a blend of Tuscan heritage and contemporary design, just 15 mins away from the renowned hilltop town of ...
  • 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 €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
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
  Special Offer

#4
  1. Italy
  2. Tuscany
  3. Siena
from €470per 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: Balcony / Terrace / Patio
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, 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, 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: 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, 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: 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, 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, 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, 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, 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, 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: 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 €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
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 €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
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards: Autumn, Garden, Pool, Scenic View, Spring, Summer, Winter
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
Capanna al Lago, Chianti Heritage in Vineyards
  •   6
  •   3
  •   3
  •   200 m2
  Special Offer
from €380per 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
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 €656per 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