Entire home
Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song
Villa in Radda in Chianti with fitness centre and outdoor pool
Photo gallery for Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song





5 bedrooms7+ bathroomsSleeps 104305.6 sq ft
Popular amenities
Explore the area

- Place, Castello di Albola
- Place, Castello di Radda Winery
- Place, Borgo di Vescine - Tenute di Castelvecchi
- Airport, Florence (FLR-Peretola)
Rooms & beds
5 bedrooms (sleeps 10)
Camera Avorio
1 Queen Bed
Camera Azzurra
1 Queen Bed
Camera Gialla
1 Queen Bed
Camera Rosa
1 Queen Bed
Camera Verde
1 Queen Bed
7 bathrooms, 1 half bathroom
Ensuite Bathroom of Camera Avorio
Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Ensuite Bathroom of Camera Azzurra
Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Ensuite Bathroom of Camera Gialla
Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Ensuite Bathroom of Camera Rosa
Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Ensuite Bathroom of Camera Verde
Soap · Towels provided · Bathtub or shower · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Garden-Level Bathroom (Patio Entrance)
Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer
Hallway Half Bathroom (Ground Floor)
Soap · Toilet  · Shampoo
Watchtower Bathroom
Soap · Bidet · Toilet · Shower only · Shampoo
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area
About this property
Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song
Just a 5-minute walk from the heart of Radda in Chianti, the capital of the Chianti Classico wine region, Villa Le Rondini is the only luxury villa in Chianti within walking distance of a town. This unique 17th-century estate unites noble Tuscan heritage with refined modern comfort—offering guests both the charm of village life and the serenity of a private countryside retreat.
Perched between Siena and Florence, the villa’s ancient watchtower, built over 450 years ago to guard Siena, now offers breathtaking panoramas of vineyard-clad hills glowing in golden evening light. Once a noble residence and winemaking centre, the property has been meticulously restored over five years with the finest Tuscan artisans, reviving stone walls, handmade terracotta floors, vaulted ceilings, and Renaissance-inspired detailing.
Each of the five suites is individually styled in soft hues of blue, pink, green, yellow, or ivory, with curated artworks and bespoke furnishings creating a sense of timeless elegance. While steeped in history, the villa provides every modern comfort, including a Loxone smart-home system, ambient lighting, and underfloor radiant heating and cooling for year-round comfort.
Outdoors, guests can unwind by the private pool, dine al fresco beneath covered verandas, or relax on panoramic terraces surrounded by manicured gardens softly illuminated at night. The expansive lawn offers both a peaceful retreat and an elegant setting for intimate events and celebrations. A private service entrance and on-site parking ensure convenience and discretion.
Perfectly positioned between Siena, Florence, and San Gimignano, Villa Le Rondini is more than a holiday home—it is a living piece of Tuscan history, restored with devotion to offer an authentic and unforgettable escape in the heart of Chianti.
Perched between Siena and Florence, the villa’s ancient watchtower, built over 450 years ago to guard Siena, now offers breathtaking panoramas of vineyard-clad hills glowing in golden evening light. Once a noble residence and winemaking centre, the property has been meticulously restored over five years with the finest Tuscan artisans, reviving stone walls, handmade terracotta floors, vaulted ceilings, and Renaissance-inspired detailing.
Each of the five suites is individually styled in soft hues of blue, pink, green, yellow, or ivory, with curated artworks and bespoke furnishings creating a sense of timeless elegance. While steeped in history, the villa provides every modern comfort, including a Loxone smart-home system, ambient lighting, and underfloor radiant heating and cooling for year-round comfort.
Outdoors, guests can unwind by the private pool, dine al fresco beneath covered verandas, or relax on panoramic terraces surrounded by manicured gardens softly illuminated at night. The expansive lawn offers both a peaceful retreat and an elegant setting for intimate events and celebrations. A private service entrance and on-site parking ensure convenience and discretion.
Perfectly positioned between Siena, Florence, and San Gimignano, Villa Le Rondini is more than a holiday home—it is a living piece of Tuscan history, restored with devotion to offer an authentic and unforgettable escape in the heart of Chianti.
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Amenities
Pool
Kitchen
Washing machine
Dryer
Air conditioning
Gym
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- Pool
- Free WiFi
- Air conditioning
- Outdoor space
House Rules
Check in after 3:00 PM 
Minimum age to rent: 18 
Check out before 10:00 AM 
Children
Children allowed: ages 0–17 
Events
Events allowed: family gatherings, birthday parties, weddings 
Must be requested in advance. T&Cs apply.
Pets
No pets allowed 
Smoking
Smoking is not permitted 
Check-out instructions
The host requires you to complete the following before checking out: 
Remove personal items 
Turn off the lights and return the keys 
Check-Out Step 1 – Before Leaving the Villa
- Please make sure you have collected all your personal belongings.
- Return all keys to the designated place. 
Check-Out Step 2 – Before Closing the Villa
- Switch off all lights, air conditioning, and water taps.
- Help us save energy and keep the villa sustainable. 
Failure to complete these may result in a negative review from the host.
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 cash 
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 77 
Note from host: Must be requested in advance. T&Cs apply. 
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property 
Host has indicated that there is a smoke detector on the property 
Safety features at this property include a fire extinguisher and a first aid kit 
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 
Property Registration Number 052023LTN0124, IT052023C2ZAOYP98I
We should mention
This property does not have any lifts 
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 EUR 5000, due to national regulations; for further details, please contact the property using the information in the booking confirmation
About the area
Radda in Chianti
Located in Radda in Chianti, this villa is in a rural area. Castello di Radda Winery and Castello di Albola are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chianti Sculpture Park and Arno River. Borgo di Vescine - Tenute di Castelvecchi and Gianfranco Carla Fineschi Botanical Rose Garden are also worth visiting. Relax and indulge in the area's health/beauty spas, or seek out an adventure with hiking/biking trails, cycling and horse riding nearby. 

Radda in Chianti, Province of Siena
What's nearby
- Castello di Albola - 6 min drive - 6.1 km
- Castello di Radda Winery - 7 min drive - 2.2 km
- Il Molino di Grace Winery - 12 min drive - 10.7 km
- Meleto Castle - 13 min drive - 10.7 km
- Borgo di Vescine - Tenute di Castelvecchi - 19 min drive - 7.9 km
Getting around
Restaurants
- Osteria Al Ponte - 11 min drive
- Locanda Podere Le Vigne - 16 min walk
- Lo sdrucciolo - 1 min walk
- Badia a Coltibuono - 11 min drive
- BAR Ucci - 11 min drive
Frequently asked questions
Reviews
Reviews
No reviews yet
Be the first to leave a review for this property after your stay.
About the host
Hosted by Brandon Yeoh Cheng

I’ve always been drawn to the art of meaningful connection — the kind that happens around a table, through stories, and through care in the smallest details. Inspired by the idea of “unreasonable hospitality,” I believe genuine warmth comes from thoughtfulness — from noticing the little things that make someone feel truly seen. Hosting in Tuscany allows me to express that philosophy fully, creating moments that feel both effortless and deeply personal.
Why they chose this property
Radda in Chianti is one of those rare places where time seems to slow down just enough for you to truly see. Set among rolling hills and heritage vineyards, it offers an unmatched combination of history, authenticity, and quiet sophistication. Each evening, the valley transforms under golden light, with sunsets that spill across olive groves and ancient stone walls — a view that never fails to feel magical, no matter how many times you’ve seen it.
What I love most about this area is its balance — refined yet unpretentious, deeply rooted yet endlessly inspiring. It’s a place for those who appreciate heritage, comfort, and the beauty of life lived slowly.
What I love most about this area is its balance — refined yet unpretentious, deeply rooted yet endlessly inspiring. It’s a place for those who appreciate heritage, comfort, and the beauty of life lived slowly.
What makes this property unique
The property is the only 17th-century villa located just a short three-minute walk from the centre of a village in Chianti, and that village is Radda in Chianti, the capital of the Chianti Classico wine region. The house is equipped with state-of-the-art smart-home lighting and underfloor heating and cooling, eliminating the need for traditional air conditioning or radiators.
Being right by the village centre, there are numerous public parking areas nearby, and the villa itself offers two large on-site parking spaces, ideal for weddings and private events. Its unique location allows you to stroll into Radda for an evening drink and return to the villa feeling as though paradise lies just within reach.
Being right by the village centre, there are numerous public parking areas nearby, and the villa itself offers two large on-site parking spaces, ideal for weddings and private events. Its unique location allows you to stroll into Radda for an evening drink and return to the villa feeling as though paradise lies just within reach.
Languages:
English, Italian
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