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Villa I Cipressini Tuscany Private luxury pool spa

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Pool
Property video
Pool
Interior
Living area

Reviews

10 out of 10
Exceptional
5 bedrooms7 bathroomsSleeps 10

Popular amenities

  • Private pool
  • Hot tub on site
  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washing machine

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

2 Single Beds

7 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Bathroom 6

Bathroom 7

Spaces

Kitchen
Balcony
Separate dining area
Garden

About this property

Villa I Cipressini Tuscany Private luxury pool spa

The vacation villa is furnished in a simple, yet graceful country chic featuring comfortable spaces and terraces where you can gather as a group for meals and reminiscing, be it about your last Tuscan adventure or moments of friendship. The villa provides two large living rooms each providing soft cozy sofas gathered around a fireplace. From the first sala, you can access an incredible terrace which promises excellent views from morning till night. This terrace can also be reached from an external stairway.

Meals can be enjoyed outdoors or in the full dining room, with also provides direct access to the patio, garden and splendid country views. There is an eat-in kitchen which is supplied with complete sets of table and cookware, dishwasher and large fridge. It is here where you can experiment with the local recipes or you can arrange to have a private chef come in and tantalize you with the flavors of the region. This floor also includes a guest bathroom.

The villa will accommodate up to 10 persons in its 5 bedrooms with en suite bathrooms. In the main house, you will find 2 accommodating double bedrooms, each with an en suite bathroom complete with all bed, and bath linens. The villa includes a clothes washer (and dryer) and there's a easy WiFi access for emails and internet. There are two bedrooms arranged with two single beds, perfect for friends traveling together, children or young adults. The last bedroom suite is located in the dependancè only 5 meters from the main villa.

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About the area

Pienza

Pienza is home to this holiday home. Chiesa di San Francesco and Palazzo Piccolomini are local landmarks, and some of the area's activities can be experienced at Enoteca Di Ghino and Triacca Winery. Travelling with kids? Consider RI Crea RE and Art Studio di Adelina Quadri. Spend some time exploring the area's activities, including golfing.
Map
Pienza, Siena

What's nearby

  • Pieve di Corsignano - 16 min walk - 1.4 km
  • Historic Centre of Pienza - 18 min walk - 1.5 km
  • Palazzo Piccolomini - 18 min walk - 1.5 km
  • Pienza Cathedral - 19 min walk - 1.7 km
  • Piazza Pio II - 19 min walk - 1.7 km

Getting around

  • Foiano della Chiana Station - 29 min drive

Restaurants

  • ‪Pizzeria Bar L'Officina del Gusto - ‬10 min drive
  • ‪Bar Il Casello - ‬3 min drive
  • ‪Caffe Dante - ‬10 min drive
  • ‪Trattoria Vecchio Forno - ‬10 min drive
  • ‪Non Solo Bar - Rendezvous - ‬8 min walk

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 59 out of 59 reviews
Rating 8 - Good. 0 out of 59 reviews
Rating 6 - Okay. 0 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Susan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a wonderful week! The villa was better than expected highlights were: recently renovated bathrooms for every bedroom, the spa room with a huge hot tub to relax in after a day of touring, comfortable outdoor patio, gorgeous pool and views and an easy walk to town through fields and olive trees.
Stayed 7 nights in May 2026
Verified

10/10 Excellent

Ruth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This villa was AMAZING ! Perfect luxurious accommodations.. met all of our requirements… clean , spacious, lovely frie place and outdoor grill. Bath facilities were lovely, hot water plentiful, bed so comfy. Location was PERFECT! Short walk to beautiful Pienza.. easy quick drive to beautiful Montipulciano. Our host , Thiago , was superb. One guest lost luggage and Thiago retrieved it from Florence Airport and DROVE IT TO THE VILLA!! Amazing and above and beyond.. we so enjoyed our stay and will return when possible but would recommend to my dearest friends and family to stay in this most lovely place!!
Stayed 14 nights in Mar 2026
Response from VrboOwner on 3 Apr, 2026
Thank you so much for your kind words! It was a real pleasure hosting you, and I’m so glad to hear you enjoyed your stay. Knowing that you appreciated the space and the experience means a lot to me. You’re always welcome back anytime Ruth! I’d be happy to host you again in the future!
Verified

10/10 Excellent

Tucker J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thiago was very attentive. The house was great. Pienza and surrounding area were beautiful
Stayed 6 nights in Nov 2025
Response from VrboOwner on 7 Mar, 2026
Thanks for the description and compliments Tucker, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified

10/10 Excellent

leigh t.

Liked: Cleanliness, communication, location, listing accuracy

Lovely Stay

Beautiful villa in a beautiful setting, walkable to Pienza and overall great stay.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Leigh!
Verified

10/10 Excellent

Susan J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous Iconic Tuscan farmhouse!

Fabulous Tuscan farmhouse in a perfect location for a group of friends wanting to experience all that Val D’Orcia has to offer!
Stayed 7 nights in Oct 2021
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Susan!
Verified

10/10 Excellent

David H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay!

Stunning house and grounds. Thiago was a great communicator and arranged a chef for us one night. Just trying to figure out when we can return - thanks Thiago!
Stayed 7 nights in Jun 2022
Response from VrboOwner on 6 Sept, 2023
Thank you for taking the time to share your thoughts on I Cipressini. We are happy to learn that your recent stay was an enjoyable experience and it gives us great pleasure to read your kind words. We hope to welcome you at I Cipressini soon. Best regards and many thanks David! "I Cipressini"
Verified

10/10 Excellent

Christopher H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful spacious villa, great location, amazing pool, incredible sunsets!

Our family had a wonderful time staying at Villa I Cipressini! We had plenty of space with even a few beds to spare for our family of 5! Thiago was a wonderful host—check in and check out were a breeze, and communication was very easy and quick. The pool and spa area are top notch, and the sunsets were truly incredible. We enjoyed stayed here right in Pienza and made fun day trips to Montepulciano, Montalcino, and Siena. We will certainly try to stay here again on our next visit to Tuscany!
Stayed 5 nights in Jul 2024
Response from VrboOwner on 18 Feb, 2025
Thanks for the description and compliments Christopher, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified

10/10 Excellent

Jane H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Postcard perfect Tuscan family holiday

Our family group of 9 - 3 generations ages 15- 81 - had a wonderful stay at this villa. The layout was excellent - each bedroom with it’s own bathroom, large dining room with window facing the sunset and well equipped kitchen. We appreciated being able to walk into Pienza- and it is great location for exploring nearby towns. Thiago connected us to a chef - we enjoyed a cooking lesson and a gourmet meal over 2 evenings.
Stayed 7 nights in Sep 2022
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Jane!
Verified

10/10 Excellent

Marc M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay

Communication with Thiago was great and the house is just amazing. Very close to Pienza by walk and the location is just unbelievable. Whaouuuu no critic can be done. Jacouzy, laundry, swimming pool to relax, very practical kitchen… this a dream house
Stayed 7 nights in Aug 2022
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Marc!
Verified

10/10 Excellent

Lauryn M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home and great location!

We rented this home with a group of friends to celebrate my 40th birthday. The house was just as described and extremely convenient for getting into Pienza. We found it to be very clean and the bathrooms and spa room are newly renovated and very nice. Thiago was extremely helpful while we made reservations and planned our trip. Highly recommmend!
Stayed 5 nights in Mar 2022
Response from VrboOwner on 6 Sept, 2023
Thank you so much for the compliment Lauryn, we are very pleased to be able to give our guests a fabulous vacation. We appreciate your kind review, we put maximum effort and a lot of passion. Thanks again! I Cipressini
Verified

10/10 Excellent

Will S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Desn't get any better tha this villa!

The villa is even better than the pictures show. It is great! The proximity to Pienza - just beautiful a short walk- makes for full enjoyment of the villa and the town. Thiago, property manager, is very responsive and helpful. Our entire party was impressed and enjoyed their time at the villa.
Stayed 28 nights in May 2022
Response from VrboOwner on 6 Sept, 2023
Thank you for taking the time to share your thoughts on I Cipressini. We are happy to learn that your recent stay was an enjoyable experience and it gives us great pleasure to read your kind words. We hope to welcome you at I Cipressini soon. Best regards and many thanks "I Cipressini"
Verified

10/10 Excellent

Surrey W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A DREAM RENTAL!!!

We were six family members aging from four years old up to 74 years old and had the time of our lives at this house! Thiago was beyond helpful and answered my WhatsApp messages throughout the whole time. We were there with various questions we adored Pienza, which was only a two minute drive away and spent quite a bit of time there. We also took day trips to Montalcino and Montepulciano. We loved and used the hot tub room more than a few times. The scenery and sunsets were incredible. Seriously a dream location! Thank you, Thiago for all your help!
Stayed 5 nights in Mar 2025
Response from VrboOwner on 13 Apr, 2025
Thank you so much for your kind words! It was a real pleasure hosting you, and I’m so glad to hear you enjoyed your stay. Knowing that you appreciated the space and the experience means a lot to me. You’re always welcome back anytime — I’d be happy to host you again in the future!
Archival

10/10 Excellent

Spring break family holiday

We loved everything about Cipressini! It felt like we were staying in the country, but it was very near the wonderful town of Pienza! As the previous reviewer stated, the rooms are quite large, and had every convenience. The central location in Tuscany made it the perfect home-base for exploring other beautiful hilltop towns. We even took advantage of the train service in Chiusi to make a fun day-trip to Rome! We hope to stay here again, and would very highly recommend this beautiful holiday home to others who truly want an authentic Tuscan experience!
Response from VrboOwner on 6 Sept, 2023
We are very happy that you spent a good holiday. Thank you for your generous review; hope to see you again!
Verified

10/10 Excellent

Dee S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific family vacation

This was our second time staying at this amazing property. Thiago was very responsive after our booking and providing recommendations and even booking dinner reservations. The chef he recommended, Giancarlo from The Tuscan Chef, was absolutely amazing! It will be an unforgettable 85 birthday dinner. During our stay. Thiago was very responsive and is very easy to work with. The villa is just as breathtaking as we remembered. We were glad to share this trip with our spouses. Everyone was very comfortable and satisfied with their stay. The spa room was used frequently. Only regret is that we were not able to use the pool, with it’s amazing views, as much due to the cooler weather. I will definitely be returning for visit #3.
Stayed 11 nights in May 2025
Response from VrboOwner on 7 Mar, 2026
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Archival

10/10 Excellent

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Great Place to Stay

This was our second time to stay at Il Cipressini and we plan to go again. It is a very comfortable house with fine bathrooms and a very workable kitchen. The views from the house are lovely. The owner is very accomidating and takes care of everything. The location of the house is ideal for seeing the best of and most beautiful parts of Tuscany. It is anywhere from 10 minuets to less than an hour to all the sights of Tuscany. It is located a comfortable 10 minuite walk to downtown Piensa, a very historic hilltop town which has several good restaurants. We highly recommend staying at Il Cipressi.
Response from VrboOwner on 6 Sept, 2023
We are very happy when we are able to offer our guests a nice holiday. We make continuous improvements and new works to provide a holiday to remember with great pleasure. Thank you so much. Andrea & Elisabetta
Verified

10/10 Excellent

Kris F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home in Pienza Tuscany!!

We had a wonderful stay at I Cipressini!! The home is perfect for a large group. There were four couples and we each had a beautiful bedroom suite with amazing views of the country side. The house is immaculate and very comfortable. There are several areas to sit outside to take in the views! We enjoyed having the private chef for the evening and the wine tasting trip that Thiago arranged for us. The town of Pienza is nearby so we we’re able to walk into town for dinner. We all hope to return one day! Thank you!
Stayed 3 nights in Sep 2019
Response from VrboOwner on 6 Sept, 2023
We are very pleased to be able to give our guests a fabulous vacation. We appreciate your kind review, we put maximum effort and a lot of passion. Thank you so much for how you leave the house. Hope to see you soon. Thank you Kris!
Verified

10/10 Excellent

Maria P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise in Pienza

The most beautiful property we have ever stayed at! The amenities at the villa were wonderful and grounds were magnificent. it was peaceful and relaxing by the pool or in the hot tub. Pienza is a 15 minute walk and is a cute little town with the nicest people, restaurants, shops, and grocery store for any essentials needed. Communication with the host, Thiago, was excellent and he was very helpful with anything we asked for. He helped us arrange a private chef at the villa for my husband's birthday which was delicious and felt like we were at a restaurant. Book this villa, you will be very happy that you did!
Stayed 7 nights in Aug 2022
Response from VrboOwner on 6 Sept, 2023
Your review is stunning Maria! Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much!
Archival

10/10 Excellent

I Ciprissini, pienza

We rented this home for 2 weeks while we took italian lessons. It was perfect!! We had our road bikes with us and there are so many rides you can do from the house. The gentleman who meets you at the house and runs the Bar il Casello in town, Paulo, was wonderful. He met us, explained the house and area and even helped us make reservations for dinner. The house is big - 3 bedrooms and 3 bathrooms. It is located a perfect distance from the town of Pienza. A short walk to town for dinner. We loved the house and the area. We would highly recommend it.
Response from VrboOwner on 6 Sept, 2023
We are very pleased to be able to give our guests a fabulous vacation. We appreciate your kind review, we put maximum effort and a lot of passion. Hope to see you soon. Thank you.
Verified

10/10 Excellent

Katina R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Tuscan Villa

We took a trip with 6 of our friends to Tuscany for 4 days and were lucky enough to stay at this amazing villa. From the second we booked the trip, Thiago was amazing! He helped arrange wine tasting tours, a personal chef in the villa with cooking lessons and airport transfers. When we arrived he had left us a beautiful platter of cheeses and meats. The villa is truly beautiful with attention to every detail. The pictures do not do it justice. We loved everything about it, but the sunsets and views were our favorite. We plan to return and spend even more time! Thank you Thiago.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 13 Jun, 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Katina!
Verified

10/10 Excellent

Laura K.

Liked: Cleanliness, check-in, communication, listing accuracy

Experience of a Lifetime A+++++

Experience of a lifetime. Just returned from the most amazing week at II Cipressini. Family of 5. Three adult children in their 20s. Spacious, clean, walk to town, Pienza is a gem. Time has stood still in historic downtown Pienza. Views from Villa are breathtaking. The II Cipressini hosts will steer you to home chefs, tours, restaurants etc. Great spot for families, couples, and friends to explore all the neighboring towns and wineries in Tuscany as well as Siena and Florence. Book without hesitation. Family from Westchester NY.
Stayed 7 nights in Aug 2023
Response from VrboOwner on 13 Jun, 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Laura!
Verified

10/10 Excellent

Bryan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place to enjoy Tuscany!

We recently returned from an amazing stay at I Cipressini. The house itself was situated right outside the town of Pienza, offering a perfect location to both walk to a charming town, but also to explore different areas of Tuscany. The house was very clean, well stocked, and the views from the house were breathtaking. There is tons of room for a group to enjoy this house. Thiago is an amazing host. He is extremely responsive both before the trip and during the stay, and is ready to help you make the most of your trip. He helped us setup a private cooking class at the house, a wine tour, and helped provide recommendations and personally secured reservations on our behalf throughout our stay. All of which made the trip special. I'm grateful to have found Thiago and this property, and highly recommend.
Stayed 4 nights in Oct 2019
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments Bryan, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified

10/10 Excellent

William H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent property

We had 3 families with 6 adults & 4 children……great accommodations. …4 bedrooms & 4.5 bathrooms in the main house.& a 1 bedroom /1 bath guest cottage which was our “ grandparents “suite.We walked to Pienza every morning on the dirt path across the owner’s property; my guess is about 15 minutes ,maybe 1 km. Of course the grandchildren loved the swimming pool,especially after day trips plus the temperature was very high. The location is great for exploring Tuscany as Montepulciano is a 15 minute drive & Montalcino is 25 minutes. Thiago was most helpful & was available with quick responses to our questions. He also recommended private chefs to prepare dinners for our families; the cost was much less than going to restaurants & really enhanced our stay.
Stayed 6 nights in Jul 2022
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much William!
Verified

10/10 Excellent

Elizabeth D.

Beautiful escape in Tuscany near an amazing town

I stayed in this property for nearly 2 weeks with my family (2 adults and 3 young children). The house is wonderful: updated spaces, comfortable beds/bedrooms, updated bathrooms, classically beautiful (and fully stocked) kitchen. We could not have asked for more. The grounds and pool area were well-maintained and provided gorgeous views of rolling hills and beautiful sunsets. There were also some amazing running / biking paths across the road that wind through olive groves and mideval churches. Lastly - the property manager was extremely responsive and very helpful. We had several questions beforehand and during our stay and they were always reachable and prompt. They also helped us organize several dinners to be prepared at the home with a chef during our stay. I could not recommend this home more!
Stayed 11 nights in Jul 2018
Response from VrboOwner on 6 Sept, 2023
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. We hope to always meet the needs of all, we work for this. Thanks and see you soon.
Verified

10/10 Excellent

Michael S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Unique property

The house and property are fantastic. It is perfect size for a large, multi-generational family trip. Thiago was extremely responsive before and during our stay. He helped arrange for the outstanding chef, Giancarlo from Tuscan Chef, to come to the house. He also helped arrange day trip to Florence. Montepulciano, Siena, and smaller towns are easy drive. The views are incredible, especially to the West and North. The best and most unique aspect, though, is the walking path to Pienza. The only hard part is crossing the street; once over you are walking through fields and then a shaded path to the walls of the town. Air conditioning was typical for Europe and opening the windows was often better option; they had screens.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 13 Jun, 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Michael!
Verified

10/10 Excellent

Jeffrey S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Classic Beautiful Tuscan Villa

Our group of four couples had a great experience at this Villa. It was even more beautiful than the pictures. Great indoor and outdoor spaces for visiting with friends in the relaxed country side. The location is perfect for visiting Brunello focused wineries. Also a great spot for visiting nearby towns such as Montecino, Pienza, and Montepulciano. There is a pedestrian walkway with beautiful views if you don’t have a car and want to walk 20 minutes into Pienza for dinner. We also visited places like Voltara and San Gimignano by drier. Most evenings we brought in a Chef recommended by the house manager, Thiago. The cooking class at the Villa was a lot of fun for our group and the food very good. If you are staying more than two nights make sure to stop at a market on your way to the house for extra Shampoo, Coffee, and Tolite paper as stocked supplies at the house are very limited.
Stayed 5 nights in May 2023
Response from VrboOwner on 13 Jun, 2024
Thanks for the description and compliments, we are proud when our guests spend a nice holiday and appreciate what we offer with our property. Thank you so much Jeffrey!
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