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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

Exterior
Property video
Exterior
Pool
Pool
5 bedrooms7+ bathroomsSleeps 104305.6 sq ft

Popular amenities

  • Gym
  • Dryer
  • Fireplace
  • Washer
  • Kitchen
  • Parking available

Explore the area

View in a map
  • 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.
Our prices include all fees. No hidden fees.

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Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Gym

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House Rules

Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
Must be requested in advance. T&Cs apply.
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Pets

No pets allowed
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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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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.
Map
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

  • Monteriggioni Castellina Station - 24 min drive
  • Peretola Airport (FLR) - 76 min drive

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

Does Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song?

Check-in begins at 3:00 PM.

What time is check-out at Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song?

Checkout is at 10:00 AM.

Where is Villa Le Rondini – In the Heart of Chianti, the Swallows Find Their Song located?

Situated in a rural location, this villa is 1.6 mi (2.5 km) from Castello di Radda Winery and within 6 miles (10 km) of Castello di Albola and Church of San Sigismondo. Borgo di Vescine - Tenute di Castelvecchi and Il Molino di Grace Winery are also within 6 miles (10 km).

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About the host

Hosted by Brandon Yeoh Cheng

Host profile image
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 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.

Languages:

English, Italian
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