9 Best Vrbo Vacation Rentals In Pienza, Italy - Updated 2021

vrbo pienza italy

Visitors coming to romantic Tuscany will feel like they’re in a scene from Under the Tuscan Sun as they stay in traditional stone villas, drive through the rolling countryside, and visit villages and cities such as Florence for their historical landmarks, gardens, art galleries, and museums. Enjoy the scenic beauty of Mt. Amiata, the green meadows filled with cypress trees and poppies, and nearby vineyards and olive groves as you meander through the Tuscany region. During the summer months enjoy the numerous festivals and live music scene before returning to your villa and watching the tangerine-coloured sunsets over the famed Tuscan landscape. To enjoy your vacation to beautiful Tuscany more fully, please check out the list below of the best Vrbo vacation rentals in Pienza, Italy before finalizing your travel arrangements.

1. Tuscan farmhouse with stunning countryside views (from USD 1086)

Visitors will enjoy staying at this classic stone farmhouse in beautiful Tuscany with wood beams and stonework throughout while being surrounded by the rolling hillside and cypress trees. After a day biking throughout the medieval villages nearby or vineyards synonymous with the region, visitors will enjoy relaxing under the Tuscan sun at the pool area. Enjoy preparing veal Milanese or spinach manicotti in the fully stocked kitchen and then dining outside on the spacious patio with your family while enjoying the sun set over the hillside. Visitors can enjoy using amenities such as internet, the hot tub, fitness room, and washing machine while drying your clothes in the fresh air on a clothes line since there is no dryer.

The original symbol of Tuscany Private luxury villa, pool spa Pienza Siena Italy
31 reviews
villa 5 Bedrooms 7 Bathrooms
Top guest reviews
Amenities & Room:
The kitchen is very well equipped with plenty of dishes
we felt like we owned the expansive sky and the breath-taking Tuscan landscape
There is outdoor furniture although only two of the chairs are loungers
Every room was very comfortable with its own bathroom and two extra bathrooms were also very helpful (one in the spa room and one downstairs adjacent to the living room)
Odd when there is a beautiful dining room seating 6 to 8 people comfortably
As the previous reviewer stated the rooms are quite large and had every convenience
The vistas took your breath away
The house is absolutely beautiful with plenty of rooms
The common areas had plenty of space for large groups to spread out and also offered areas to sit quietly and read a book
A basic grocery list and dinner was waiting for us on the first night (we had arranged this prior to our trip) and it was perfect to start our adventure there
Owner was attentive and very responsive when needed
The owner provided us with a huge bowl of fruit a huge wheel of local Pecorino cheese as well as olive oil
explained the house and area and even helped us make reservations for dinner
eat swim and watch a fabulous sun set each evening
We had several questions beforehand and during our stay
We found that the Pienza 491 wine shop in the village was great talk to Allessandro there for good suggestions and wine tastings
The pool setting which overlooked the Tuscan valley was both a great relief from the August warmth and a great place to just hang out and enjoy Tuscany's beauty
We had a great time in Tuscany in this villa it has a wonderful location just outside Pienza about 250 m off the main road
I Cipressini Please note there are 15 stairs up to the entrance of the villa Not a problem for us but may be for some
It is located a perfect distance from the town of Pienza A short walk to town for dinner
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2. Traditional villa with gorgeous mountain views (from USD 1198)

After a day visiting Florence to check out the Accademia for Michaelangelo’s David, sample delicious gelato flavours at the the International Gelato Festival booths, or wander the gardens of the Pitti Palace, then return home and relax in one of two courtyards with beautiful hanging wysteria, lavender, and rose bushes. During the summer months, guests can enjoy swimming in the pool surrounded by olive trees and stunning views of the rolling hills and mountains. Enjoy dining on the terrace, eating a margherita pizza prepared in the fully stocked kitchen or wood oven and drinking a glass of wine from one of the nearby vineyards while gazing over the stunning Italian landscape. Visitors will enjoy provisions such as internet, a laundry room, and plenty of parking space for their vehicle during their stay.

Luxury Tuscan villa, heated pool, spectacular views, underfloor cooling
21 reviews
villa 5 Bedrooms 6 Bathrooms
Top guest reviews
Amenities & Room:
The furnishings are very tasteful and high-quality from the bedding to the bathrooms to the fabulous and expansive kitchen
The kitchen is a delight and the appliances are top of the line
There was plenty of seating for the 4 couples that were in our party
We spent our days exploring and our evenings enjoying the comforts of the villa and cooking in the amazing kitchen
The views out over the valley could be seen from the 2 outside patios and the bedrooms
The views are breathtaking The house is well furnished with everything you can imagine and more
She is also a great cook
The housekeeper was also very knowledgeable and helpful with any questions we had
and she was so helpful
informative and very generous and Samuela the kind and friendly housekeeper cooked wonderful meals for us
the owner was attentive
are out of this world
lovely shops and memorable restaurants
The grounds surrounding the villa are perfectly maintained by the property's gardener and the views from every vantage point are breathtaking
The main house has all the charm of a historic Tuscany farm house however every modern luxury convenience is provided for
- It does not get much better than that The Villa is perfectly located between Rome and Florence and nestled among numerous historic Hill Towns - Pienza Montepulciano
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3. Classic Tuscan home with sweeping vistas (from USD 482)

After spending some time enjoying the Saturnia and its thermal baths or some of the numerous vineyards throughout the area, enjoy sitting by the pool and soaking up the sun while enjoying a glass of prosecco. Enjoy dining al fresco in the gazebo while taking in a beautiful sunset over the stunning lush green landscape dotted with cypress trees, rolling hills, and mountains. Guests will enjoy traditional details such as the stone walls and archways and the exposed wooden beams while staying at this villa which is within driving distance of numerous villages. Amenities for visitors to use during their Tuscan escape include parking, internet, a fully stocked kitchen, and washing machine.

Beautiful private villa with private pool, WIFI, TV, pets allowed, parking, close to Montepulciano
Pienza, Tuscany, IT
13 reviews
villa 7 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
one of the apt has a larger fridge and a larger table to sit more people
What was great: If we wanted privacy each house could grant privacy since each section had kitchen bathroom
also kitchen little comfort when you like to Cook youself
A charming villa that felt communal yet offered privacy with the separate apartments Incredible views and the local town
We spent most of our time when we were their out side under the pergola drinking wine and reading
but we were surprised by the condition of the roads) better to access with small car-
Dino the owner was reserved but friendly and helpful
The owner Dino is very friendly and attentive
Only suggestion would be to update some appliances
but I recommend a good translation application to understand some of the explanations Other than that he is the type of guy you will love and could be friend with for a long time Overall ver...
We were 3 generations of family plus and a family friend
Beatiful setting breathaking vieuws
We used their bar-b-que a few time which was great Lots of stairs everywhere so something to think about
We really enjoyed feeling totally alone far away from traffic
The property is situated in a very peaceful area with beatiful views
The kids loved running around in and out of the house exploring this relatively large property with so many different little cornersThe view is the perfect tuscany postcard you can ever imagine f...
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4. Stunning Tuscan stone villa (from USD 388)

Enjoy taking cooking classes while staying at this Tuscan villa with immaculate stone work including stone arches, stone walls, and exposed wooden beams. Enjoy sleeping in the canopy bed while experiencing refreshing breezes flowing through the bedroom windows and waking up to the panoramic landscape of green meadows, oaks, cypresses, and nearby Pienza. After walking through the streets of Pienza and admiring its historical structures and monuments, return home and enjoy sitting on a lounger in the secluded pool area. Enjoy dining on the large terrace after preparing breakfast in the fully stocked kitchen before heading out to explore nearby Monticchiello.

Your piece of Heaven: Pure Relax in a charming & historical Villa
11 reviews
villa 4 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
I loved cooking in the kitchen
The property itself is gorgeous as is the surrounding landscape
Rooms great with their own bathrooms - a big plus for 8 people Only one room with air conditioning
so it was a bit hot at night during this heat wave but fans made it fairly comfortable at night
large bathrooms well equipped with all the necessities and a kitchen dining and living area that accommodated our needs very nicely
The property had cats (which we loved and fed) and small and large pigs
(the bath products were wonderful and there was always plenty of fresh towels)
Anna met us when we arrived and she showed us around the villa and explained how appliances
She gave us her contact number in case
She was wonderful and responded quickly when contacted
replies helpful in coordinating our Chef experience patient with my many questions and our late arrival and so very welcoming
This made our visit even more enjoyable
The best sunset over Pienza Very good location for visiting nearby towns
The villa location made our trips into Pienza for meals and shopping very easy Trips to Montepulciano Monticchiello
By far this was the very best
The pool still needs a bit of work but it was fine for most of our stay
This place is absolutely gorgeous not only because of its scene but also because of the beauty of the Villa So quiet and in harmony with nature felt like it was a magic spot on earth
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5. Villa with breathtaking views and swimming pool (from USD 218)

Enjoy breathtaking views of Mt. Amiata and the surrounding landscape from the travertine pool and garden area with roses and lavender during your stay at this traditional Tuscan villa. Visitors will enjoy being within driving distance to medieval villages and large centers, Siena and Florence, where they can enjoy the numerous festivals, art scene, dining spots, Boboli gardens, and other historical attractions. Amenities for guests to enjoy include parking, WiFi, a fully stocked kitchen to prepare meals, a spacious living room for families to relax and socialize, and a canopy bed to top off the romantic feel of the Tuscany region.

Podere Lamino with Swimming pool
1 review
House 4 Bedrooms 4 Bathrooms

6. Abode just within walking distance of Pienza (from USD 151)

After taking time in Florence to explore the fashion scene, including Museo Della Moda E Del Costume which houses the creative designs of fashion powerhouses Versace, Aramani, Valentino, and Saint Laurent, come home and sit in the shade under the many trees in the grove area outback. Enjoy the terracotta floors, exposed beams, and stonework of the villa while experiencing stunning views of the distant mountains from the villa’s many windows. Visitors can enjoy taking in the sunshine while sitting under an umbrella in the courtyard surrounded by flowers while sipping on wine from one of the local wineries. Enjoy cooking meals in the fully equipped kitchen and using the WiFi and parking during your stay.

Villa Arpicella Pienza Siena Italy Tuscany, a stunning, green, peacefull corner
7 reviews
villa 2 Bedrooms 1 Bathroom
Top guest reviews
magnificent view friendly hosts and lovely Tuscan house
but once you get there you never want to leave
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7. Holiday home by the rolling Tuscan hillside (from USD 163)

After spending a day in Florence admiring the Renaissance masterpieces, canvases of Michaelangelo, and sculptures at the Uffizi Gallery, indulging in gelato, and dining at one of the numerous restaurants in Piazza della Signoria, return home and cool off in the infinity pool while enjoying spectacular views of the hillside. Return home from exploring nearby Siena for its art, culture, and cathedral and sit out on the terrace enjoying the surrounding garden with olive, citrus, and cypress trees. Enjoy using the fully stocked kitchen during your stay to prepare meals before heading out on strolls through the lush hillside or driving around the surrounding vineyards for wine tastings. Visitors can enjoy the parking, WiFi, living room, and the cool terracotta floors during their stay in Tuscany during the summer.

Holiday house Pienza for 1 - 2 persons - Holiday home
2 reviews
House 0 Bedrooms 1 Bathroom

8. Lovely brick home in Pienza

Step out of the front door onto the lovely floral gardens and head a short distance to explore historical Pienza’s shops, Piazza Pio II, and restaurants. After spending a day checking out the village or nearby Tuscan vineyards, return home and enjoy sinking into one of the comfy armchairs located in the dining/living area. Enjoy preparing small meals in the fully stocked kitchen and dining under the white crystal chandelier while reminiscing about the day’s adventures before retiring to the bedroom decorated in calming green and white. During their stay visitors can enjoy WiFi and parking for their vehicle as they explore the nearby Tuscan hillside full of vineyards, olive groves, and medieval villages.

Small lovely house in Pienza
4 reviews
Apartment 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
the cookware and stemware is more than adequate and the furnishings are comfortable
the details in each room with the guests in mind were lovely
we enjoyed the many shops the local cooperative of wine and olive oil two minutes from the apartment
the bathroom was everything you would expect in a good hotel
it is clean and comfortable with all the modern conveniences and the location is excellent
the hosts were terrific
antonio was so helpful in making our stay enjoyable
Read more reviews

9. Beautiful stone apartment with views of Mt. Amiata

After spending time exploring nearby villages to enjoy some of the summer’s festivals, come home and take a refreshing dip in the pool while experiencing stunning views of Mt. Amiata. Visitors can enjoy cooking meals in the fully stocked kitchen and dining in the open plan dining area next to the living room where they can enjoy socializing afterwards. Enjoy cycling through the country side filled with fields of poppies while meeting some of the local deer, birds, porcupines, and hares during your exploring the surrounding region. Visitors can use amenities such as internet, parking, and an outdoor patio to dine in peace.

Agriturismo Selvoli - Istrice
1 review
farmhouse 3 Bedrooms 3 Bathrooms

Exploring the stunning region of Tuscany

Enjoy staying like a local in one of these traditional Tuscan villas while enjoying the beautiful countryside famed for its rolling hills, cypress trees, olive groves, and vineyards. Make certain to stop by in Florence to visit the Accademia and buy your tickets at the box office in Piazza della Signoria to avoid the lines, stop for an afternoon gelato break, visit the Pitti Palace and Boboli gardens with stunning views of the city, and walk along the Arno river watching the row boats pass under the Ponte Veccio. Enjoy wine tasting at some of the region’s oldest vineyards, indulging in award-winning cuisine, and checking out the numerous historical sights of the area. While visiting Tuscany, don’t forget to enjoy a cannoli, gelato, or tiramasu along with traditional pasta dishes before returning home for the evening to your accommodations at one of the best Vrbo rentals in Pienza, Italy.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Writer living in British Columbia who loves to travel and explore new destinations. I also enjoy engaging in new activities during my travels such as Hydrospeeding in France. Solo travelled to...Read more

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