Entire home
Tuscan Villa with private swimming pool
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Reviews
9.6 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 8400 sq m
Popular amenities
Explore the area
Castellina in Chianti (SIENA), Tuscany
- City Hall Castellina In Chianti
- Walls of Monteriggioni23 min walk
- Archaeological Museum of Chianti
- 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
⸻
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!
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
⸻
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
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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House Rules
Check in after 4:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs and cats less than 23 kg per pet (limit one pet total)
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
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
We should mention
All guests, including children, must be present at check-in and show their government-issued photo ID card or passport
Cash transactions at this property cannot exceed USD 5000, due to national regulations; for further details, please contact the property using the information in the booking confirmation
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 Gaiole in Chianti Stadium. Relax and indulge in the area's winery tours, or seek out an adventure with cycling, hiking/biking trails and mountain biking nearby.
Castellina in Chianti (SIENA), Tuscany
Getting around
Restaurants
- Villa Lecchi - 22 min drive
- Bar Brancaia - 9 min drive
- Il Cantuccio - 6 min drive
- Foresteria Villa Cerna - 14 min drive
- Ristorante Albergaccio di Castellina - 7 min drive
Frequently asked questions
About the host
Hosted by Owner/ Property Manager
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.
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 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.
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
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