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Villa I Cipressini Tuscany Private luxury pool spa

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Interior
Property video
A spacious living room with a fireplace, a sofa set, and a dining area with a table and chairs.
A dining table set for two with a view of a sunset through an arched window.
A heated pool

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms7 bathroomsSleeps 10500 sq m

Popular amenities

  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View map
Pienza, Siena
  • Place, Pieve di Corsignano
    ‪16 min walk‬
  • Place, Historic Centre of Pienza
    ‪18 min walk‬
  • Place, Pienza Cathedral
    ‪19 min walk‬

Room options

About the area

Pienza

A family-friendly stay in Pienza awaits you at this holiday home. Within a 20-minute stroll, you'll find Historic Centre of Pienza and Pienza Cathedral. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .You can enjoy a TV with a DVD player, and home features free WiFi, 7 bathrooms and a fireplace. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a dishwasher. A balcony, a living room and a dining area are also available. Limited housekeeping is available. .Enjoy the gym, Hot tub and sauna. Additionally, you'll find laundry facilities, a games room and a garden. .Sights within a 20-minute walk of this Pienza holiday home include Pieve di Corsignano and Artemisia Gallery.
View more Holiday homes in PienzaOpens in a new window

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
  • ‪Pummaro - ‬17 min walk
  • ‪Caffe Dante - ‬10 min drive
  • ‪Bar Il Casello - ‬3 min drive
  • ‪Trattoria Vecchio Forno - ‬10 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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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Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub
  • Massage
  • Private pool
  • Sauna

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Wheelchair-accessible parking available
  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 7 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Stereo
  • TV with cable/satellite channels
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • One pet total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Accessible parking space
  • In-room accessibility
  • Well-lit path to entrance
  • Wheelchair-accessible parking
  • Wheelchair-accessible pool
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Things to do

  • Arcade/game room
  • Bicycle parking
  • Cooking classes
  • Gym
  • Heated pool
  • Golfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
  • Fire extinguisher

General

  • Bicycle parking
  • Double-glazed windows
  • Electric car charging station
  • Garden
  • Locally-owned and organised tours and activities
  • Some LED lighting used
  • Unit size: 5,382 square feet
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 3:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Maximum 1 pets
    • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.

Events

Events allowed: family gatherings, birthday parties, weddings

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts debit cards
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30
Long-term renters welcome
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30. Long-term renters welcome. For guests' safety, the property includes a fire extinguisher in all accommodation.

Property Registration Number IT052021B5SFHQRFAA

We should mention

  • All guests (including children) need to be present at check-in to show their government-issued photo ID or passport.
  • On-site cash transactions can't exceed EUR 5000, due to national regulations. For more details, please contact the property using information in the booking confirmation.

Property is also known as

Original Symbol Tuscany Villa-pool Heart Tuscany Pienza-si
Original Symbol Tuscany Villa-pool Heart Tuscany
Original Symbol Tuscany Villa-pool Heart Tuscany Pienza-si
Original Symbol Tuscany Villa-pool Heart Tuscany Pienza-si
150822

Frequently asked questions

Does Villa I Cipressini Tuscany Private luxury pool spa have a pool?

Take your pick from a heated pool, a pool and a communal pool.

What luxury perks are available at Villa I Cipressini Tuscany Private luxury pool spa?

This property features a heated pool, as well as a private pool and a fireplace.

What makes Villa I Cipressini Tuscany Private luxury pool spa a romantic place to stay?

1 hot tub, private pools, and fireplaces all help set the scene for a sizzling getaway at Villa I Cipressini Tuscany Private luxury pool spa.

Is Villa I Cipressini Tuscany Private luxury pool spa family-friendly?

You bet! With amenities such as an arcade and laundry facilities, as well as highchairs and travel cots, it's no surprise that Villa I Cipressini Tuscany Private luxury pool spa is a winner with our family travellers.

Is there a private hot tub at Villa I Cipressini Tuscany Private luxury pool spa?

Yep, there is a hot tub.

Is there a free airport shuttle available at Villa I Cipressini Tuscany Private luxury pool spa?

No, Villa I Cipressini Tuscany Private luxury pool spa does not offer an airport shuttle service.

What time are check-in & check-out at Villa I Cipressini Tuscany Private luxury pool spa?

Check-in begins at 3:00 PM. Check-out time is 10:00 AM.

Villa I Cipressini Tuscany Private luxury pool spa Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 60 out of 60 reviews
Rating 8 - Good. 0 out of 60 reviews
Rating 6 - Okay. 0 out of 60 reviews
Rating 4 - Poor. 0 out of 60 reviews
Rating 2 - Terrible. 0 out of 60 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

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
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
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
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
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
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
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
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
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
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
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!
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.
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
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
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
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.
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
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
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
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
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
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
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
Verified

10/10 Excellent

scott h.

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

Better Than Imagined

From the very first moment we drove onto the property of I Cipressini we knew we were in for something very special! The property photos, while quite stunning in themselves, simply don't do justice to how beautiful the property is in person. The layout of the villa was easy to navigate and designed to take advantage of Tuscany's sunsets. The added bonus of having a separate one-bedroom annex building was perfect for our family as it gave our adult kids their own space while my wife and I enjoyed our privacy. 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! I should note that Thiago was quite wonderful throughout the entire process, from booking to arrival, to all the other small requests/needs we had during our stay. It would be an understatement to say that I Cipressini is a wonderful villa...it is so much more!!!
Stayed 7 nights in Aug 2019
Verified

10/10 Excellent

Cindy H.

Everything we dreamed of!

If you have ever dreamed of renting a home in Tuscany and exploring the surrounding villages, this is your dream come true! This home is immaculate, beautiful, and comfortable. The owners are friendly, welcoming, and responsive to any needs you may have. The house is within close walking distance to Pienza, which is perfect for your morning coffee and people watching. The town is lovely! The owner referred us to a local chef who came to us for a full evening of cooking together and it was one of the highlights of our trip. There is so much to do and see within day trips of this house that we wished we had more time there instead of moving on! The owners have recently completed the addition of a beautiful Spa to the property, complete with a large window for viewing the Tuscan sunset from the jacuzzi. This lovely home is perfect for all types of groups traveling together. The bedrooms are large, the beds comfortable, AND each bedroom has its own bathroom. If we ever get opportunity, we will definitely stay here again! If you are lucky enough rent this home, you won’t be disappointed!
Stayed 4 nights in Apr 2019

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