We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

House Rentals in Pienza, Italy

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    Travelers to Pienza are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $121
    / Night
    Payment Protection
    View Details
    1 / 23
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
    Overview Make Inquiry
    From
    $182
    / Night
    Payment Protection
    View Details
    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    From
    $1,818
    / Week
    View Details
    1 / 33
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    From
    $1,433
    / Week
    View Details
    1 / 16
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Il Ristoro is a country house which was originally one of the first examples of European hospitals. The building, completely refurbished in 2012, is in the heart of the Val d’Orcia valley, an area marked by enchanting landscapes and the most varied Medieval towns. From its central location, you... View all property information
    Make Inquiry
    Location Information
    53026, Pienza, Province of Siena
    From
    $7,980
    / Week
    Payment Protection
    View Details
    1 / 64
    6 Bedrooms / 6 Bathrooms / Sleeps 13
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Highlights Independent farmhouse that sleeps 13 people. The main house sleeps 6. On the ground floor there are a large living room with fireplace, library, hi-fi, TV, DVD, small kitchen, a double bedroom with a separate entrance from the outside with an en-suite bathroom with washing machine.... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $6,412
    / Week
    Payment Protection
    View Details
    1 / 54
    Monticchiello
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Highlights This very well furnished farm is situated in one hundred and fifty hectares of farm land producing excellent extra virgin olive oil, the farmhouse is set on a natural terrace overlooking the beautiful valley below. The house was built in the first half of the 18th century and has been... View all property information
    Make Inquiry
    Location Information
    Monticchiello, Pienza
    From
    $11,390
    / Week
    Payment Protection
    View Details
    1 / 42
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Highlights This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin. A beautiful garden surrounds the elegant farmhouse and a lovely swimming pool looks over the Val... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $495
    / Night
    View Details
    1 / 35
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    6 Double Bedrooms - Pool Villa Calanchi is a 19th century Tuscan farmhouse divided into three. It is hard to believe that seven years ago the property lay in ruins.“All the materials we used to restore the building were reclaimed” the owners explain “some we found lying around in the fields, and... View all property information
    Make Inquiry
    Location Information
    53026, Pienza, Province of Siena
    From
    $3,632
    / Week
    Payment Protection
    View Details
    1 / 63
    7 Bedrooms / 7 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Highlights This beautiful farm house is situated in fifty hectares of land with olive trees, a vineyard and also walnut trees. A very well appointed and furnished residence. Air conditioned in apartment four only. An independent farm house that sleeps 11+1. Apartment 1 (sleeps 3) on the ground... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $14,875
    / Week
    View Details
    1 / 47
    4 of 5 stars (1) Very good
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Hot Tub
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 and... View all property information
    Make Inquiry
    Location Information
    53026, Pienza, Province of Siena
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $4,273
    / Week
    View Details
    1 / 25
    Monticchiello
    6 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Monticchiello is a magical place. A village enclosed by medieval walls but connected to the world through the vibrant culture that has characterized it for years, this villa is very near Monticchello and overlooks the most beautiful section of Val D'Orcia.L'Apparita is situated under a kilometer... View all property information
    Make Inquiry
    Location Information
    Monticchiello, Pienza
    From
    $4,063
    / Week
    View Details
    1 / 31
    6 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 swimming... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $3,553
    / Week
    View Details
    1 / 45
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Hidden at the end of a long drive through never ending fields of wheat, guests will find this enchanting farmhouse surrounded by a typical Mediterranean garden with rosemary, lavender, sage and flowers in every season. The colours of the countryside surrounding Pienza Villa inspire the interior... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $3,853
    / Week
    View Details
    1 / 28
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa Fiordaliso is perfect for those looking to spend their holiday in a home away from home with stunning views of the Tuscan landscape. Perfect for families and large groups of friends. Additional amenities include: heating. View all property information
    Make Inquiry
    Location Information
    53020, Pienza, Province of Siena
    From
    $4,455
    / Week
    View Details
    1 / 29
    Monticchiello
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Situated on a farm of 150 hectares that produces excellent extra virgin olive oil, this farmhouse is set on a kind of natural terrace overlooking the lovely valley below. The house, built in the first half of the eighteenth century, has been renovated carefully by the couple who owns it and who... View all property information
    Make Inquiry
    Location Information
    Monticchiello, Pienza
    From
    $8,029
    / Week
    View Details
    1 / 25
    7 Bedrooms / 8 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This large farmhouse dates back to the 10th century as an important post-house for changing coaches and horses along the Via Francigena. This history is reflected in its architecture. The interior is finely decorated with wooden furniture and terracotta tile floors. On the first floor is a large... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $4,411
    / Week
    View Details
    1 / 54
    Monticchiello
    7 Bedrooms / 5 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    On a large estate surrounded by olive groves and flower fields, this Italian villa is just the place if you and your group are looking for beauty and tranquility. Whether its sunrises in the morning, sunsets in the evening, or midday gazing, you’ll have views that will take your breath away while... View all property information
    Make Inquiry
    Location Information
    53026, Monticchiello, Pienza
    From
    $3,302
    / Week
    View Details
    1 / 37
    5 Bedrooms / 6 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This marvelous villa is located in the heart of Tuscany, near the enchanting town of Pienza, and is the ideal villa for anyone looking for a relaxing and peaceful getaway in Tuscany. Additional amenities include: heating. View all property information
    Make Inquiry
    Location Information
    53020, Pienza, Province of Siena
    From
    $13,903
    / Week
    View Details
    1 / 40
    Monticchiello
    10 Bedrooms / 9 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    As a luxury villa, Villa Bandida works best as a place where friends and family come to relax, share meals, explore the countryside and drink wine late into the evening. For guests looking for the perfect location for a group get-together, relaxing break, birthday celebration or wedding, Villa... View all property information
    Make Inquiry
    Location Information
    Monticchiello, Pienza
    From
    $9,081
    / Week
    View Details
    1 / 26
    9 Bedrooms / 9 Bathrooms / Sleeps 19
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa Rombi is a beautiful Tuscan property located in Contignano. The spacious villa sleeps up to 19 guests in the main house and annexe. It is surrounded by breathtaking views over the Italian countryside.Villa Rombi has been beautiful decorated with a relaxed, modern Tuscan style. There is a... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    Get the List
    From
    $6,138
    / Week
    View Details
    1 / 23
    6 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Situated between Monticchiello and Montepulciano in a secluded and extremely quiet area is an attractive farmhouse surrounded by lavender and rosemary bushes. The large garden overlooks the valley like a terrace from where you can see one of the loveliest views in the area. The house has excellent... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $9,081
    / Week
    View Details
    1 / 24
    8 Bedrooms / 9 Bathrooms / Sleeps 19
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    For visitors in search of an exceptional and luxurious Italian retreat, Villa Casella is the perfect choice. The exquisite villa is located in Contignano and surrounded by spectacular views of rolling clay hills and countryside. The villa sleeps up to 19 in 8 very spacious bedrooms: 2 twin, 5... View all property information
    Make Inquiry
    Location Information
    Pienza, Province of Siena
    From
    $2,642
    / Week
    View Details
    1 / 17
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A charming holiday home for a relaxing break and good base for exploring Tuscany and beyond. Villa Torrita is an attractive 16th century property with a large garden and pool, surrounded by beautiful landscape of hills and valleys. Additional amenities include: heating. View all property information
    Make Inquiry
    Location Information
    53049, Pienza, Province of Siena
    From
    $1,259
    / Night
    View Details
    1 / 36
    8 Bedrooms / 7 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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. Additional amenities include: heating. View all property information
    Make Inquiry
    Location Information
    53026, Pienza, Province of Siena