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.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Tuscan farmhouse with stunning countryside views (from USD 885)
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.
Top guest reviews
Amenities & Room:
The kitchen is very well equipped with plenty of disheswe felt like we owned the expansive sky and the breath-taking Tuscan landscapeThere is outdoor furniture although only two of the chairs are loungersEvery 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 comfortablyCleanliness:
As the previous reviewer stated the rooms are quite large and had every convenienceThe vistas took your breath awayThe house is absolutely beautiful with plenty of roomsThe common areas had plenty of space for large groups to spread out and also offered areas to sit quietly and read a bookA 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 thereHost:
Owner was attentive and very responsive when neededThe owner provided us with a huge bowl of fruit a huge wheel of local Pecorino cheese as well as olive oilexplained the house and area and even helped us make reservations for dinnereat swim and watch a fabulous sun set each eveningWe had several questions beforehand and during our stayRead more reviewsLocation:
We found that the Pienza 491 wine shop in the village was great talk to Allessandro there for good suggestions and wine tastingsThe 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 beautyWe had a great time in Tuscany in this villa it has a wonderful location just outside Pienza about 250 m off the main roadI Cipressini Please note there are 15 stairs up to the entrance of the villa Not a problem for us but may be for someIt is located a perfect distance from the town of Pienza A short walk to town for dinner
2. Traditional villa with gorgeous mountain views (from USD 797)
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.
Top guest reviews
Amenities & Room:
The furnishings are very tasteful and high-quality from the bedding to the bathrooms to the fabulous and expansive kitchenThe kitchen is a delight and the appliances are top of the lineThere was plenty of seating for the 4 couples that were in our partyWe spent our days exploring and our evenings enjoying the comforts of the villa and cooking in the amazing kitchenThe views out over the valley could be seen from the 2 outside patios and the bedroomsCleanliness:
The views are breathtaking The house is well furnished with everything you can imagine and moreHost:
She is also a great cookThe housekeeper was also very knowledgeable and helpful with any questions we hadand she was so helpfulinformative and very generous and Samuela the kind and friendly housekeeper cooked wonderful meals for usthe owner was attentiveRead more reviewsLocation:
are out of this worldlovely shops and memorable restaurantsThe grounds surrounding the villa are perfectly maintained by the property's gardener and the views from every vantage point are breathtakingThe 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
3. Stunning Tuscan stone villa (from USD 321)
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.
Top guest reviews
Amenities & Room:
I loved cooking in the kitchenThe property itself is gorgeous as is the surrounding landscapeRooms great with their own bathrooms - a big plus for 8 people Only one room with air conditioningso it was a bit hot at night during this heat wave but fans made it fairly comfortable at nightlarge bathrooms well equipped with all the necessities and a kitchen dining and living area that accommodated our needs very nicelyCleanliness:
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)Host:
Anna met us when we arrived and she showed us around the villa and explained how appliancesShe gave us her contact number in caseShe was wonderful and responded quickly when contactedreplies helpful in coordinating our Chef experience patient with my many questions and our late arrival and so very welcomingThis made our visit even more enjoyableRead more reviewsLocation:
The best sunset over Pienza Very good location for visiting nearby townsThe villa location made our trips into Pienza for meals and shopping very easy Trips to Montepulciano MonticchielloBy far this was the very bestThe pool still needs a bit of work but it was fine for most of our stayThis 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
4. Villa with breathtaking views and swimming pool (from USD 171)
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.
5. Abode just within walking distance of Pienza (from USD 135)
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.
Top guest reviews
Host:
magnificent view friendly hosts and lovely Tuscan houseRead more reviewsLocation:
but once you get there you never want to leave
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.
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