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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 1377 Villas in Pienza with updated reviews, rates, and availability.

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Pool

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi

10.0 out of 10, Exceptional, (45)
"Luigi went above and beyond in providing suggestions of restaurants and things to do in the area. He was also helpful when we were have trouble calling our car rental….always willing to help out and answer questions. The home is very clean and has the old Italian rustic charm. The beds were comfortable. There is no AC but fans are provided for every room. There were beautiful sunsets every night by the pool. The views of the rolling Tuscan hills were spectacular. The color and intensity of the...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (48)
"We received a warm welcome from the family and a thorough explanation of the facilities, the surrounding area and places of interest. Fabrizio communicated easily with us using the translation phone app. The apartment is very clean, well equipped and offers a genuine Italian experience. Simply wonderful."
The price is SAR 578
SAR 661 total
includes taxes & fees
17 Feb - 18 Feb
Il Poggio dell'Eremita
Villa with private pool and panoramic view in beautiful Val d'Orcia
Pool

Villa with private pool and panoramic view in beautiful Val d'Orcia

10.0 out of 10, Exceptional, (5)
"We had stayed at this property for years before Jennifer purchased it. And do hope to continue. We appreciate the effort and care to details she put into updating it and providing an excellent experience. This property is well located to see numerous villages in the area."
Villa with private pool and panoramic view in beautiful Val d'Orcia
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Water, Plant, Sky, Building, Swimming Pool, Azure, Tree, Shade, Outdoor Furniture, Grass

Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the

Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Villa Podere Belvedere
Beautiful villa with private pool, terrace, large lawn, and panoramic Tuscan views

Villa Podere Belvedere

9.8 out of 10, Exceptional, (11)
"Our stay at Villa Podere Belvedere was just wonderful. Our family had the most relaxing time at the Villa, enjoying morning walks in the picturesque country side, lovely lunches by the pool and driving to the many charming Towns in the area all contributed to a wonderful stay. My only negative comment is that it would have been helpful if we had been informed that absolutely no household cleaning products or catering supplies would be provided, we could have brought these items with us. Given...
Villa Podere Belvedere
Villa in Montalcino, exclusive for you, stunning view!!!
Exterior

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (78)
"We absolutely loved our stay at this villa! It was just wonderful, and Luigi was a fantastic host! The views from every part of the villa are amazing! It was so fun to see all of the sheep each morning and watch the sunset in the evenings. We were fortunate enough to be in town for the olive festival in Montisi, the quaint little village just a few miles away. We had a blast! The recommended chef who cooked for us at the villa, Giancarlo from the Tuscan Chef, was incredible! What a fantastic...
Villa in Montalcino, exclusive for you, stunning view!!!
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Pool, house, & garden with Tuscan farms below & medieval town of Cortona.

Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool

10.0 out of 10, Exceptional, (46)
"This property is all it explains to be. The stay included myself, my husband, my daughters and their families. The property is spectacular, the rooms as beautiful as shown. The guesthouse was perfect for my daughter, her husband and 2 young children. The travel cots were perfect and opening the chest of toys brought so much joy to my 2 year old granddaughter. We utilized the kitchen and pizza oven and have such wonderful memories to hold. Our only disappointment was that the pool heater was not...
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool
Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Pool

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi

Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo

Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo

10.0 out of 10, Exceptional, (25)
"Xx"
Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo
Villa Casale Silvia Large Private Pool, A/C, WiFi
Beautiful villa with two annexes, private pool, jacuzzi, terrace, and garden

Villa Casale Silvia Large Private Pool, A/C, WiFi

9.8 out of 10, Exceptional, (18)
"Very nice villa to relax in the countryside. The town of Fabro is only a 15 minute ride to restaurants, train station(free parking) and other shops. We found the villa to be very spacious and relaxing. One item to note, there was seven cats (at the time of our stay) living outside the doors of the property. We were told to feed, some bring some cat food."
Villa Casale Silvia Large Private Pool, A/C, WiFi
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Pool

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

9.4 out of 10, Exceptional, (21)
"Family of 7 adults spent 1 week in beautiful secluded Tuscan farmhouse. Great location for visiting the region - Arezzo short drive. Florence Pisa approx. 1.5 hours. Beautiful hilltop villages, olive groves and vineyards. Quintessential Tuscany!"
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Country House With Private Pool
Pool

Country House With Private Pool

10.0 out of 10, Exceptional, (3)
"This is a larger authentic Tuscan farmhouse with a lovely lush garden. The house has a rustic feel with lots of the furniture made by the hosts, the pool and garden are beautiful to relax and take in the views. Many of the sights in southern Tuscany and Umbria are close by (by car). The property is clean and the beds and bathrooms are very comfortable. The hosts are very discreet but will make you feel very welcome. Definitely would visit again! "
Country House With Private Pool
Villa Il Melograno - Four Bedroom Villa, Sleeps 8
Pool

Villa Il Melograno - Four Bedroom Villa, Sleeps 8

10.0 out of 10, Exceptional, (8)
Villa Il Melograno - Four Bedroom Villa, Sleeps 8
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Pool

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (10)
"We were a family group of 15 ranging in age from 20 to 92. We used the pool every day. Laughed at the clothes dryer because they have the same kind in Portugal where we vacationed. Many people walked into Camucia and enjoyed the restaurants grocery stores etc. Several of us have been to Italy before my first time in Assisi but we shared experiences with them. Staff was prompt to arespond to any problems. And a week of perfect weather makes it all the better"
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Villa Larniano, With Private Pool And View On Vineyard
Pool

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (64)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (7)
"Our Anglican Church friends (three couples) from Texas began our Italy tour in Rome and then continued to Florence for a few days. We spent our final four days at the beautiful Villa Santa Chiara, a short walk from the gates of downtown Siena, Italy. This wonderful villa could accommodate more people than our group of six, but it was an excellent choice for our three couples. Each couple had their own private apartment with a bathroom, kitchen, and spacious living area. The villa was...
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Villa Miralaghi from the private heated swimming pool 5x8 1,40 constant depth.

Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,

9.4 out of 10, Exceptional, (41)
"Our group of five women thoroughly enjoyed our two-week stay at Miralaghi. We were in the main house (old hunting lodge) with 4-bedrooms, 3 baths, huge living space, kitchen, carport, and private pool. Miralaghi is a unique property, located between Paciano and Moiano, high up on a hillside. It is very peaceful, quiet and provides lovely hiking trails on the huge, 750 acre property. It's a perfect retreat at the end of a day of visiting nearby hill towns. Our host, Mausi, was a delight and so...
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren

Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren

10.0 out of 10, Exceptional, (1)
"Bellissimo casolare ben tenuto con magnifico giardino e grande piscina. La padrona di casa gentilissima e molto discreta. Abbiamo soggiornato in agosto con amici e ci siamo trovati benissimo. Assolutamente consigliato!"
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Outdoor

Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino

Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Pienza

Hotel San Gregorio
Outdoor pool

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (110)
"Very nice staff, great service, super clean. Will stay again."
The price is SAR 477
SAR 548 total
includes taxes & fees
19 Feb - 20 Feb
Hotel San Gregorio
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
D'ell Osteria

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (1)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Casanova - Panoramic Rooms and Suites
Aerial view

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (42)
"It was a nice property- unfortunate what they charge to just swim"
The price is SAR 651
SAR 736 total
includes taxes & fees
13 Mar - 14 Mar
Casanova - Panoramic Rooms and Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do villas in Pienza cost?
Rates for villas in Pienza range between SAR 578 and SAR 578 per night. No matter your budget, you’ll find something that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Pienza?
Pienza has 1377 villas to choose from. Find your ideal stay quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
Why book your villa in Pienza with Expedia?
Use Expedia to find your ideal villa in Pienza. Taking the kids on a break? Use our filters to search for stays with perks like a swimming pool. If you have a set budget, select how much you want to spend and your preferred star rating. We’ll help you find the perfect fit that suits your taste and style.
How can I find cheap villas in Pienza?
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