Located in Castellina in Chianti in Tuscany, Italy, 'Isola Serena' is a beautiful private luxury villa on 4 acres of land with the most breathtaking views in the Tuscan countryside. Overlooking Siena and covered in vineyards, olive groves, and captivating forestry, this brand new villa just finished restoration in June 2014 and recently expanded in 2023 to include 2 additional guesthouses. The property now has a total of 10 bedrooms and can sleep up to 23 people, making this one of the biggest villas in Chianti and a self-contained private resort. The villa was restored by local Italians of the highest standard to maintain the Tuscan culture, artisanal tradition, and craftsmanship, whilst complemented by modern furniture and contemporary amenities.
Some of the finest quality local materials that were used include hand-made terra cotta floors, Italian marble and travertine for the terraces and bathrooms, chestnut windows and doors, and walnut for the kitchen and library.
The main house is 440 sq metres (4500 sq ft) with 6 bedrooms and all ensuite bathrooms and a library which can be used as a proper bedroom. It includes a large terrace overlooking the countryside, a beautiful brand new large 66 x 13 ft private infinity pool, a small plunge pool, multiple barbeque areas, a newly built children's playground with enclosed sandbox onsite, a gym, full kitchen, dining room, library, free WIFI, satellite TV, and all modern amenities that are perfect for cooking, entertaining, and relaxing.
In 2023, we recently expanded the property to also include 2 additional beautiful private guesthouses (each guesthouse is 600 sq ft) with each guesthouse having two bedrooms with ensuite bathrooms. 1 guesthouse has one bedroom with an ensuite bathroom and kitchenette, and adjacent to it, there is a second separated bedroom with an ensuite bathroom. The 2nd guesthouse is a private house with two bedrooms that each have ensuite bathrooms, a kitchen, and a TV area.
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Events allowed: family gatherings and birthday parties
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Pets
No pets allowed
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Smoking
Smoking is not permitted
Absolutely no smoking inside villa.
To secure your booking, a 25% reservation deposit is required at time of booking. Balance is due 60 days prior to your arrival.
Cancellations made between date of booking, up to 60 days before arrival date carry a 25% penalty of accommodation cost.
Cancellations made less than 60 days before arrival carry a penalty of 100% of accommodation cost.
Important information
You need to know
Property Registration Number IT052005C2SZJXAFTJ
Property # 3808832
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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 25
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 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
About the area
Castellina in Chianti
Located in Castellina in Chianti, this villa is in a rural area and in the mountains. Chianti Sculpture Park and Archeodromo di Poggibonsi are cultural highlights, and some of the area's activities can be experienced at Mazzei Winery and Lilliano Estate Winery. Travelling with kids? Consider Chianti Observatory, or check out an event or a game at Gaiole in Chianti Stadium. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with horse riding, hiking and mountain biking.
City Hall Castellina In Chianti - 3 min walk - 0.3 km
Via delle Volte - 3 min walk - 0.3 km
Castellina Fortress - 5 min walk - 0.4 km
Archaeological Museum of Chianti - 5 min walk - 0.4 km
Getting around
Monteriggioni Badesse Station - 14 min drive
Peretola Airport (FLR) - 67 min drive
Restaurants
Bar Pizzeria Italia - 2 min walk
Cecchini Panini Truck - 13 min drive
Antica Trattoria La Toppa - 16 min drive
Bar Brancaia - 1 min walk
La Perla Del Palazzo Ristorante - 11 min drive
Frequently asked questions
Does ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views?
As of 18 August 2026, prices found for a 1-night stay for 2 adults at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views on 17 October 2026 start from NZ$26,817, 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 ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views pet-friendly?
No, pets are not allowed at this property.
How much is parking at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views?
On-site parking is available at the property.
What time is check-in at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views?
Check-in begins at 4:00 PM.
What time is check-out at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views?
Checkout is at 10:00 AM.
Where is ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views located?
This family-friendly Castellina in Chianti villa is located in the mountains, within a 5-minute walk of City Hall Castellina In Chianti, Castellina Fortress and Archaeological Museum of Chianti. Walls of Monteriggioni is 1.7 mi (2.7 km) away.
About the host
Hosted by Kalen Properties
We are from Toronto, Ontario, Canada and have been travelling to Italy for vacation over the last 20 years. The first time we visited Tuscany, we instantly fell in love with the beautiful scenery, wine, food, and culture. In the summer of 2012 on our annual Tuscan vacation, a real estate agent showed us this farmhouse which is mentioned in written historical sources as early as 1077. With over 4 acres of private land and the most breathtaking views overlooking Siena and covered in vineyards, olive groves, and forestry, we knew this was our dream home. After embarking on a 1-year restoration project and hiring all local Italians to maintain the Tuscan culture, artisanal tradition, and craftsmanship, this beautiful luxury villa is truly an oasis of serenity and perfection. The official name of the farmhouse is Podere Isola, meaning “island farm”, which the owner renamed to “Isola Serena”, meaning “serene island” and after his wife.
Languages:
English, French, German, Italian
Premier Host
They consistently provide great experiences for their guests