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Pienza Luxury Rentals

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    $1,211 Average
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    Travelers to Pienza are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    24 Matching Rentals in PienzaView all 161 rentals
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    7 Bedrooms, 6 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
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    About this property
    Owner's description: VILLAthis property - Pienza Villathis property is a private property immersed in the Tuscan countryside. It is an excellent choice for a relaxing holiday enjoying privacy with the benefit of a private swimming pool and it is also an ideal location to explore central Italy....
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    53026, Pienza, Province of Siena
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 13
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Wi-Fi
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large home in the heart of the Orcia Valley region is perfect for those looking for incredible views as well as privacy. Set amidst a large estate, this vacation rental in Tuscany is comprised of three independent units making it perfect for three families. It also features a private...
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    Pienza, Province of Siena
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short...
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    53026, Pienza, Province of Siena
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate...
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    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 12 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Balcony
    • Washer
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casanova Relais is a wonderful podere dating back to the 1600s, that has painstakingly been restored with a perfect taste. The owners have tastefully created an extremely elegant and comfortable home for modern living with spacious bedrooms, a well equipped kitchen and a beautiful swimming pool....
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    53026, Monticchiello, Pienza
    Rental Home - 8 Bedrooms, 12 Bathrooms, Sleeps 16
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    6 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just out of the fortified town of Monticchiello, in the heart of the Val D'Orcia, one finds this typical Tuscan-Sienese farmhouse surrounded by vineyards, recently restored and refurbished to become a luxury villa. The house is characterized by a central squared unit, whose windows offer a...
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    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 10 Bathrooms, Sleeps 22
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Imposing farmhouse dating back to the 18th century comprising 2 independent units (rentable only together as a private property). This beautiful 5–hectare estate is situated in quiet and panoramic location, in the heart of the Val d’Orcia region, a short...
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • DVD Player
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Beautiful stone farmhouse situated in peaceful and panoramic location near the charming medieval town of Pienza, in the heart of the Orcia Valley region. This villa which has been recently restored with all its original details preserved, comprises 3 separate...
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Villa in Southern Tuscany with Privacy and Views - Villa Altare1 / 47
    (1)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Isn't it about time you organize that family reunion you've all been meaning to do, but can't seem to figure out where to go or where to stay? This farmhouse for rent in Tuscany is a perfect destination for families coming together once again! Large, spacious, and well equipped with enough room...
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    53026, Pienza, Province of Siena
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: VILLAthis property - SIENA The villa, close to Pienza and Montepulciano, sleeps comfortably 16 adults. It has elegantly furnished living areas opening out to the yard for dining 'al fresco', BBQ, stunning views over the valley and its own swimming pool open from the 26th of...
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    53026, Monticchiello, Pienza
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casale Tranquillo in Siena-Val d'Orcia, Tuscany is an authentic farmhouse dating back to the 19th century that has been transformed into a delightful six-bedroom villa with modern conveniences. From the moment you see the traditional stone structure tucked away in the Tuscan hills, you...
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Patio
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa is in the heart of the Val D'Orcia countryside offering luxurious accomodation with a fabulous HEATED swimming pool. The entire country chic house has 6 bedrooms, 6 bathrooms, living rooms with 3 kitchens, dining room, big patio with a stunning view and a special vegetable garden. Spoil...
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    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Podere Castelletto1 / 51
    (4)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 4, 2017
    I can't say enough about this property. I just loved it. It will literally move you emotionally and pictures will never do it justice. My advice.........just let yourself go...
    Reviewed March 22, 2017
    I never stay before in a so beautiful place... simply magic! I was there with my family and my son was so happy to discover this beautiful country. I hope to come back again!
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    53026, Monticchiello, Pienza
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Villa Pienza Large Italian villa rental in Pienza near Siena - Tuscany1 / 20
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2017
    Beautifully nestled in the rolling hills between Pienza and Montalcino, this stunning, well kept villa was a summer home from home for us. With its game room, pool, gym and...
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    About this property
    Additional amenities: Full Kitchen
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Wi-Fi
    • Parking
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casale Campagna in Siena-Val d\'Orcia, Tuscany is a classic country retreat in the heart of the Tuscan hills. This little gem of a home retains its traditional charm with all the modern conveniences, making it the perfect choice for those seeking an authentic Italian experience. Enter a...
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    Location Information
    Pienza, Province of Siena
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    8 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Terrace
    • Grill
    • Washer
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional amenities: Full Kitchen
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    Location Information
    53026, Pienza, Province of Siena
    Rental Home - 8 Bedrooms, 8 Bathrooms, Sleeps 14
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Villathis property - Siena This beautiful independent villa is located in the well-known valle d'Orcia. Monticchiello is the closest town and it rises on a hill surrounded by the countryside near the town of Pienza. From the surrounding country this small village shows its...
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    Location Information
    53026, Monticchiello, Pienza
    Rental Home - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    9 Bedrooms, 9 Bathrooms, Sleeps 23 Quick View
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    • Grill
    • Private Yard
    • Parking
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    53026, Monticchiello, Pienza
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 23
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    7 Bedrooms, 8 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Balcony
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional amenities: Full Kitchen
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    Location Information
    53026, Monticchiello, Pienza
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This exclusive villa works as the perfect starting point to explore the countryside and all the art cities in Tuscany and their surroundings. It is spacious, airy, welcoming and fully equipped and accommodates up to 16 people.
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    53026, Pienza, Province of Siena
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional amenities: Full Kitchen
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    Location Information
    53026, Monticchiello, Pienza
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    • Local time: 06:28 PM (CET)
    • Exchange rate: 1 Euros = 1.14 U.S. Dollars
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