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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 1375 Villas in Pienza with updated reviews, rates, and availability.

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Outdoor dining

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

9.4 out of 10, Exceptional, (51)
"Great host, location as we wanted in Tuscany. We had villa for only our family and it was enjoyable. It is a good WiFi there, TV, kitchen. And everything you need. "
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area
Villa with pool and garden
Pool

Villa with pool and garden

Villa with pool and garden
Il Poggio dell'Eremita
Interior

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 AED 586
AED 678 total
includes taxes & fees
16 Mar - 17 Mar
Il Poggio dell'Eremita
Villa Dipendenza, Historic Holding with wonderful swimming pool
Outdoor pool

Villa Dipendenza, Historic Holding with wonderful swimming pool

10.0 out of 10, Exceptional, (36)
"We spent a week at this charming property and had an absolutely magical time with friends. The house was cozy and comfortable, with a beautiful balcony perfect for enjoying evening meals. The shared pool offered breathtaking views, and the other guests were incredibly friendly, adding to the warm atmosphere. Our host, Eloise, was exceptional—her hospitality and attention to detail made our stay even more special. She provided wonderful restaurant recommendations that we thoroughly enjoyed. We...
Villa Dipendenza, Historic Holding with wonderful swimming pool
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Outdoor pool

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

10.0 out of 10, Exceptional, (7)
"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."
Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Terrace/patio

Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany

9.8 out of 10, Exceptional, (23)
"This property is exactly as we'd imagined it to be! Very charming, great location, beautiful views! Franco and his brother were wonderful. We would definitely stay here again!"
Villa Corolle - Country House with private swimming pool in Montepulciano, Orcia Valley, Tuscany
Villa with private pool and panoramic view in beautiful Val d'Orcia
Outdoor 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
Winery Villa in the heart of Nobile Vineyards.
Interior

Winery Villa in the heart of Nobile Vineyards.

9.8 out of 10, Exceptional, (10)
"We love our stay. House and property are beautiful."
Winery Villa in the heart of Nobile Vineyards.
Stunning private villa for 4 people with A/C, WIFI, pool, TV, terrace and parking
Pool

Stunning private villa for 4 people with A/C, WIFI, pool, 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...
Stunning private villa for 4 people with A/C, WIFI, pool, TV, terrace and parking
Beautiful villa with private pool located in the hilly territory of Valdichiana, about 1 km from the
Pool

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
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Outdoor 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
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

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

The price is AED 3,893
AED 3,893 total
includes taxes & fees
31 Mar - 1 Apr
Holiday Home 'Casale I Cascetti' with Pool, Garden & Wi-Fi
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 Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (43)
"Villa Calcinaio was a beautiful place to spend our time while in Cortona. My goal was to get a slice of Tuscan life and this house gave me the opportunity to do just that. It was rustic but charming and updated ~20 years ago. Enrico was very responsive and even came to our rescue when we had trouble locating the house on the dark and rainy night when we arrived. I found the house stocked with all the basics and then some and I fell in love with the view of the beautiful dome from every...
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

I Cipressi, 5 bedrooms with pool near Cortona
Villa Montelisi, With The most Unique View On Siena (6km)
Fridge, microwave, oven, stovetop

Villa Montelisi, With The most Unique View On Siena (6km)

10.0 out of 10, Exceptional, (66)
"Villa Montelisi is now part of our family history. Everything about our stay was wonderful. Our host Lavinia made check in easy even though we arrived late. The villa with its old world charm, high ceilings, and amazing views overwhelmed us. We loved waking up to a beautiful painting of the Tuscan countryside, the large windows, balconies and patios enhanced the view, making us feel like we were in a movie. The kitchen had all the modern conveniences, so making breakfast or a late night snack...
Villa Montelisi, With The most Unique View On Siena (6km)
Villa Piandisette - Four Bedroom Villa, Sleeps 10
View from property

Villa Piandisette - Four Bedroom Villa, Sleeps 10

9.0 out of 10, Wonderful, (8)
"I really liked the villa. The rooms were ready, the beds were made. The owner welcomed us very kindly, showed us all the rooms and the pool. We were on vacation for 8 days and we really liked it, but there were a few details that spoiled our vacation a little or maybe not a little: The villa is suitable for a large number of people up to 10, but it is not very suitable for a longer stay, as I think longer than 3-4 days, because for a longer stay you want the first floor, which is the main one...
Villa Piandisette - Four Bedroom Villa, Sleeps 10
Villa Casale Silvia Large Private Pool, A/C, WiFi
Pool

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

9.8 out of 10, Exceptional, (19)
"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
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

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.
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
Seasonal outdoor pool, sun loungers

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (111)
"Very nice staff, great service, super clean. Will stay again."
The price is AED 432
AED 499 total
includes taxes & fees
16 Mar - 17 Mar
Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (43)
"It was a nice property- unfortunate what they charge to just swim"
The price is AED 648
AED 733 total
includes taxes & fees
27 Mar - 28 Mar
Casanova - Panoramic Rooms and Suites
Bosco della Spina
Exterior

Bosco della Spina

9.4 out of 10, Exceptional, (143)
"We were met by the property owner who was pleasant and informative. The room was exactly as depicted in the photos and property was in excellent condition. We would recommend to anyone staying the area at any time of year/ "
The price is AED 252
AED 277 total
includes taxes & fees
23 Mar - 24 Mar
Bosco della Spina
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 AED 586 and AED 3,893 per night. Whatever your budget, you’re sure to find a place that fits the bill with 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?
Pack your suitcase and pick from 1375 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.
Why book your villa in Pienza with Expedia?
With Expedia, it’s easy to find your dream villa in Pienza. Vacationing with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you’d like to spend and your preferred star rating. We’ll help you find the right stay in tune with your taste and style.
How can I find cheap villas in Pienza?
An excellent way to track down cheap villas in Pienza is with Expedia’s user-friendly filter tool. Narrow your search results by budget, star rating and amenities to find unbeatable rates in just a click or two.