See all properties
Entire home

Tuscan Villa with private swimming pool

Photo gallery for Tuscan Villa with private swimming pool

Exterior
Aerial view
Property grounds
Interior
Pool

Reviews

9.6 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 8400 sq m

Popular amenities

  • Private pool
  • Onsite parking available
  • Dogs and cats allowed
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Castellina in Chianti (SIENA), Tuscany
  • Place, Piazza di Santa Maria Novella
  • Place, Cathedral of Santa Maria del Fiore
  • Place, Ponte Vecchio
  • Airport, Florence (FLR-Peretola)

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Single Bed

Bedroom 5

1 Double Bed

3 bathrooms

Bathroom 1

Bathtub · Bidet · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Bidet · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Tuscan Villa with private swimming pool

The Cypresses Villa – Elegant Tuscan Retreat with Private Pool

Located in Castellina in Chianti, in the heart of Tuscany’s famous Chianti wine region, The Cypresses Villa is a beautiful stone-built home that offers the perfect balance between luxury, tradition, and relaxation. Surrounded by rolling green hills, this spacious villa is ideal for guests who love outdoor activities, as well as for those who prefer to stay in and enjoy cooking with fresh local ingredients from the neighborhood markets.

Whether you dream of reading under the cypress trees, soaking in the sun by the private pool, or enjoying a Tuscan meal by the fireplace, this villa offers an unforgettable escape.

⸻

Sleeping Area (Upper Level)
• 3 Bedrooms:
• 2 bedrooms with queen-size beds
• 1 bedroom with a double bed
• 1 additional single bed
• 2 Bathrooms:
• 1 en-suite bathroom with a shower
• 1 shared bathroom with both a tub and shower
• Extra Room: A small gym area with a few pieces of equipment (not a fully equipped gym but great for a light workout).

⸻

Living & Dining Spaces (Ground Floor)
• Living Room – Cozy space with a working fireplace, perfect for relaxing.
• Reading Room – Features a piano for music lovers.
• Dining Room – Large table for up to eight guests.
• Kitchen – Fully equipped with:
• 6 stove burners, fridge, dishwasher, freezer, oven, utensils, and a large fireplace—great for barbecuing or preparing traditional Tuscan meals.
• Additional Spaces:
• Single bedroom with easy access
• Bathroom & laundry room

⸻

Outdoor Spaces & Private Pool
• Front Patio & Terrace – Perfect for relaxing with a glass of Chianti wine, reading a book, or enjoying the Tuscan sun.
• Private Green Area – With tables and chairs for outdoor dining.
• Private Swimming Pool (Freshwater) –
• Size: 4x5 meters, depth 1.2m
• Open from May 15th – October 15th
• Exclusively for villa guests (Note: Previously, guests shared a pool, but a new private pool was added in 2017.)

⸻

Additional Amenities

FREE Wi-Fi
FREE Parking (easy parking right in front of the villa)
FREE Access to the Private Pool
BBQ & Outdoor Dining Area
Linens and towels are provided
Heater costs 50 euros per day to pay cash at check-in
⸻

Guest Experience & Important Notes
• The villa is perfect for families, small groups of friends, and nature lovers looking for a peaceful, sun-filled retreat.
• Pets are allowed, but must be approved at the time of booking.
• The property is large and green, offering plenty of space for walking, hiking, and enjoying nature.
• The road leading to the villa is a countryside road. It is not ideal for sports cars, but it is easily drivable with a regular car (just drive slowly, especially at night when crossing through the wooded area).
• Wildlife Sightings! It’s not uncommon to spot a deer or a fox while driving through this beautiful rural landscape.

Pool Safety Rules:
• Children and non-self-sufficient persons must not be left unattended at the pool.
• No pets in the water.

⸻

Distances from Key Locations
• To Town (Castellina in Chianti): 1.5 km
• To the Airport: 45 km
• To the Beach & Harbor: 85 km
• To the Train Station: 25 km
• To the Motorway: 10 km
• To the Hospital: 25 km
• To the Police Station: 1.5 km





The Cypresses Villa is a peaceful, sunlit, and elegant retreat, offering guests an authentic Tuscan countryside experience. Whether you’re exploring the world-famous Chianti wine region, enjoying homemade Italian meals by the fireplace, or relaxing in the private pool, this home is designed to provide comfort, beauty, and a true taste of Tuscany.

We look forward to welcoming you to this special piece of history and nature!

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Villa seen from the pool
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI
Vagliagli
  • Pool
  • Kitchen
  • Washing machine
  • Free Wi-Fi
10.0 out of 10, Exceptional, (68 reviews)
FAB 5BD DESIGNER VILLA, PRIVATE HEATED POOL & AMAZING VIEWS, TOP SIENA CHIANTI

House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
default

Smoking

Smoking is not permitted
I expect my guests to use common sense and pay attention to not damage the property. Pets are allowed but must be approved by the owner (fee applies)

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
On-site parties or group events are strictly prohibited
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
Property Registration Number IT052005C2IM4DT2G5

About the area

Castellina in Chianti

Located in Castellina in Chianti, this villa is in a rural area. Chianti Sculpture Park and Alta Val d'Elsa River Park reflect the area's natural beauty and area attractions include Chianti Observatory and Borgo di Vescine - Tenute di Castelvecchi. Looking to enjoy an event or a game while in town? See what's happening at Siena Stadium or Stadio Artemio Franchi. Relax and indulge in the area's winery tours, or seek out an adventure with hiking, mountain biking and cycling nearby.
View more Villas in Castellina in ChiantiOpens in a new window
Map
Castellina in Chianti (SIENA), Tuscany

Getting around

  • Monteriggioni Badesse Station - 18 min drive
  • Peretola Airport (FLR) - 66 min drive

Restaurants

  • ‪Albergo Casafrassi - ‬18 min drive
  • ‪Taverna Squarcialupi - ‬10 min drive
  • ‪Taverna di Vagliagli - ‬24 min drive
  • ‪Bar Pizzeria Italia - ‬8 min drive
  • ‪Riserva di Fizzano Hotel Castellina in Chianti - ‬20 min drive

Frequently asked questions

Does Tuscan Villa with private swimming pool have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Tuscan Villa with private swimming pool?

As of 9 April 2026, prices found for a 1-night stay for 2 adults at Tuscan Villa with private swimming pool on 28 June 2026 start from NZ$854, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Tuscan Villa with private swimming pool pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Tuscan Villa with private swimming pool?

On-site parking is available at the property.

What time is check-in at Tuscan Villa with private swimming pool?

Check-in begins at 4:00 PM.

What time is check-out at Tuscan Villa with private swimming pool?

Checkout is at 10:00 AM.

Where is Tuscan Villa with private swimming pool located?

This family-friendly Castellina in Chianti villa is located in a rural location, within 3 mi (5 km) of Castellina Fortress, Archaeological Museum of Chianti and City Hall Castellina In Chianti. Lilliano Estate Winery and Mazzei Winery are also within 6 miles (10 km).

Reviews

9.6

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. 4 out of 5 reviews
Rating 8 - Good. 1 out of 5 reviews
Rating 6 - Okay. 0 out of 5 reviews
Rating 4 - Poor. 0 out of 5 reviews
Rating 2 - Terrible. 0 out of 5 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Poul-Erik O.

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

5 great days in Italian countryside

Danish-American extended family of 7 had 5 great days at the Villa, we might have needed a minute to adjust to the rustic charm but after that we thoroughly enjoyed our stay. After warm and exhausting days traveling to Siena and Florence, everybody loved playing in the spacious pool, especially if farm dog Leo came to play! House is 5 mins from Castellina, which was a favorite town on the trip, it has everything from great restaurants, fun shopping and world class gelato. It is also just 30 mins from Siena, which (while touristy) was a nice visit. Prepare for rustic charm and don't arrive in darkness, the 3-min dirt road to the Villa is best driven during daylight!
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Adeline G.

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

Wonderful stay in a wonderful place

I stayed 2 weeks with family and friends and we all fell in love with the place ! Such a large exquisite old house, a lot of inside and outside spaces for each to enjoy some privacy. Loved the quietness, the environment so beautiful and green, the pools so enjoyable. The neighboring village is in my opinion one of the nicest place in Chianti, with plenty shops and good restaurants. Access road is bumpy yes, but really manageable. Last but not least, the owner is a delightful person, helpful, attentive but discreet, wonderful ! We are definitely thinking about returning !
Stayed 14 nights in Jul 2020
Verified

8/10 Good

James T.

Authentic Tuscan Rental Property

We recently stayed in Florence and then on a whim decided to search for a property with a little more seclusion. We found this villa close to Castellina in Chianti. The house was a little on the large size for our needs and could easily handle 2 families. The house has a great feel and is authentic to this area. It is not over developed inside but has retained it's character and was an excellent base for our exploration of the region. The realtor was efficient and the owner who lives close by extremely pleasant.
Stayed 5 nights in Jun 2018
Archival

10/10 Excellent

Carlo F.

Piacevole soggiorno

Perfetto posto per trascorrere un momento di relax. Luogo incantevole e sistemazione caratterizzata da comfort, pulizia e ordine. Merita ritornarci.
Archival

10/10 Excellent

Martin L.

BEAUTIFUL HOUSE AND PLACE

My family and I spent a week at the house , the house is even better than in the pictures and place is very charming. We had a great vacation in Tuscany and the house was in perfect location to explore around. the owner was there to help if we needed him, and he gave us some good tips. Okay we are used to the city life so I kind of miss all the services , the shops are not 24/7 but that is what you want to find in the Tuscany , right? authentic life.

About the host

Hosted by Owner/ Property Manager

Host profile image
Welcome to our family home, a special retreat nestled in the heart of the Tuscan countryside. I’m Lorenzo, your host, and I come from a long line of locals who have cherished this land for centuries. My family has owned this property since the 900s, preserving its history and traditions while adapting it to modern comforts.

When I’m not welcoming guests, I work as a professor at the University of Siena, where I share my passion for history, culture, and the rich heritage of this region. Hosting travelers allows me to connect with people from all over the world and introduce them to the beauty of Tuscany, from its breathtaking landscapes to its incredible food and wine.

This home is more than just a rental—it’s a piece of history, lovingly cared for over generations. Whether you’re here to explore the outdoors, indulge in local cuisine, or simply unwind in a peaceful setting, I’m delighted to share this special place with you. I look forward to making your stay a memorable one!

Feel free to reach out with any questions—I’m always happy to offer recommendations or help make your visit truly unforgettable.

Why they chose this property

Our home is set just outside the center of charming village of Castellina in Chianti, in the heart of Tuscany’s renowned wine region. This location offers the perfect balance between tranquility and convenience—far enough from the bustle to enjoy peaceful countryside views, yet close enough to explore the rich culture, history, and flavors of the area.

What I love most about this location is the breathtaking landscape—rolling vineyards, olive groves, and cypress-lined roads that seem straight out of a postcard. The fresh country air, the sound of birds in the morning, and the golden hues of sunset make it a truly magical setting.

The village of Castellina in Chianti, just a short drive away, is full of authentic charm with its medieval streets, local wineries, artisan shops, and family-run restaurants serving traditional Tuscan cuisine. Whether you’re here to explore historic castles, visit world-class vineyards, hike scenic trails, or simply relax by the pool, this area offers something for everyone.

This home has been in my family for centuries, and I love sharing this special piece of Tuscany with guests. I hope you’ll enjoy it as much as we do!

What makes this property unique

Our home is more than just a place to stay—it’s an authentic Tuscan retreat surrounded by nature, history, and timeless beauty. What truly sets it apart is the unparalleled scenery that changes with the light of the day, offering breathtaking views at both sunrise and sunset.

In the early morning, as the sun rises over the rolling Chianti hills, the mist gently lifts from the vineyards and meadows, creating a dreamlike atmosphere. Guests who wake early can enjoy the quiet serenity of the countryside, with nothing but the soft chirping of birds and the occasional rustling of leaves in the breeze. Sipping a morning coffee on the patio while watching the world slowly awaken is a moment of pure tranquility.

As the day unfolds, the Tuscan sun bathes the landscape in warm golden hues, making it perfect for outdoor activities—whether it’s a morning swim, a countryside walk, or an afternoon exploring nearby villages. In spring and summer, the area is full of life, with blooming wildflowers, fragrant herbs, and the vibrant green of vineyards and olive groves. Guests can experience the best of the season by tasting fresh local produce from nearby markets and wineries.

At sunset, the landscape transforms once again. The sky glows in shades of pink, orange, and deep red, reflecting off the hills in a way that feels almost surreal. This is the perfect time to unwind with a glass of Chianti wine in the private garden or on the terrace, soaking in the peaceful countryside as the last rays of sunlight fade behind the horizon. The evenings are calm, with a soft breeze and the distant hum of cicadas, creating a truly magical ambiance.

Whether you’re here for relaxation, exploration, or simply to experience authentic Tuscan living, our home offers a setting that is both timeless and unforgettable—a place where every moment feels special.

Languages:

English, French, Italian
Tell us how we can improve our siteShare feedback