Isola Serena

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.​

A Stunning Revival of Tuscan Tradition

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. 

About the Villa

Experience the perfect blend of rustic charm and modern luxury at Isola Serena, which has 1 main house and 2 guesthouses and includes 10 elegant bedrooms, each with an ensuite bathroom, and all the amenities you can imagine for a perfect stay. The expansive terrace offers breathtaking countryside views with magical sunsets every night and enjoy dipping in the stunning infinity pool overlooking the vineyards. With a children's playground, multiple BBQ areas, fully equipped kitchen, gym, and all modern facilities, Isola Serena is designed for an unforgettable experience. Stay with us and create memories that will last a lifetime.

Restoration & Expansion

The villa was completely restored in 2014 and was expanded even further in 2023 to include 2 additional beautiful private guesthouses, each of them 600 sq ft and having 2 bedrooms with ensuite bathrooms.

This is perfect for families with kids, as 1 guesthouse bedroom has a kitchenette, and the other guesthouse is a private house with two bedrooms, a kitchen, and a TV area. The villa is ideal for groups of families and friends, as everyone can still have some privacy while still being together.

An Immaculate Countryside Experience.

Our unique location offers both serenity and accessibility to nearby charming Tuscan towns and cities, ensuring a memorable stay filled with breathtaking views and unforgettable daytrips and experiences.

High chair and baby crib available upon request. Hairdryer in every bathroom. Bath and pool towels provided.

No pets allowed | No smoking

The Facilities

Infinity Pool

Dive into our stunning infinity pool with panoramic views of the Tuscan countryside. Relax on the sun loungers and soak up the Italian sunshine as you enjoy the serene surroundings.


Enjoy leisurely meals or a glass of local wine on our spacious terrace. This is the perfect spot to watch the sunset over the rolling Tuscan hills.


Designed for those that love to cook, host, or entertain large groups, this fully equipped kitchen includes high-quality appliances and all the essential cooking tools and utensils a chef needs.

Poolside Dining

Unwind in our poolside dining area and enjoy a BBQ, meal, or drink with your family and friends, seating 24 people in this relaxing shaded area with beautiful panoramic views.

Luxurious Bedrooms

Retreat to one of our elegantly designed bedrooms, each with its unique character. Enjoy a restful night's sleep with plush bedding and modern amenities.

Modern Bathrooms

Each bedroom has an ensuite bathroom with a modern shower and sink. You'll find everything you need for a refreshing start to your day.

Hear from our Guests

Our average rating is 10/10 from 40+ Reviews on VRBO

Absolute PARADISE!!!

We cannot recommend this villa highly enough!! There are no words to fully describe the beauty of Isola Serena. The main villa & new guesthouses, along with the outdoor spaces, were so thoughtfully and beautifully restored – the property was both luxurious and authentic to Tuscan style. It was easily the most beautiful place we have ever had the opportunity to stay, with views that almost seemed like they couldn’t be real! The hosts, Serena and Peter, were so kind and communicative before & during our stay. They provided an extensive list of recommendations – each one we visited was excellent! We especially loved our private dinners @ home with Chefs Andrea & Paola. Raffaella, the property manager, was so kind and showed us around the villa at check in. Both Raffaella and Serena were quickly available for any questions we had throughout our stay. Castellina was a perfect location – we loved driving into town each morning and visiting many of the local restaurants and wineries (which were spectacular). It was also a central location to adventure out to Firenze, Montalcino, and Montepulciano (all within about 1 hour or less). Even in April, we loved lounging by the infinity pool – it was straight out of a magazine! Sunsets were completely picturesque from the upper patio. Every night, we used the smaller pool which was perfectly heated to serve as a hot tub. Thank you SO much, Serena, Peter & Raffaella – you made Castellina feel like home, and we can’t wait to return!!

Jaclene F.

Best week ever!

We stayed at Isola Serena for my 50th birthday trip/celebration. There were 3 couples and 3 single women in our group. The property was even more beautiful in person than the beautiful photos you see on the listing. It’s indescribably gorgeous. We loved that every bedroom was en suite. The kitchen was well appointed. Matteo and Natalia provided anything we needed and facilitated a smooth check-in and out process. The Sonos system was awesome! We would play music by the pool and different music in the kitchen. We hired Chef Matisse for 2 dinners. We would defined recommend him. The hikes around the property were a perfect way for us to work off the pasta and wine. The pool was also wonderful for laps or hanging out. The views are unbelievable. The location is perfectly central for visiting all of the adorable and historic towns around Chianti. The beds were comfortable and we woke up every morning rested and ready for a new day of exploring the region. The patio was also a wonderful spot to hang out. We had a few dinners outside, as well. This was literally one of the best weeks of my life and Isola Serena was a key part of it. I cannot wait to go back. I am in love with Italy and in love with this property. Thank you for sharing it with us.

Dave M.

THE Best Family Vacation!

Our stay at Isola Serena was hands down the best family vacation we’ve ever had! The villa is simply perfect- from the incredible views surrounding the property, to the gorgeous infinity pool, to the herb and tomato garden, to relaxing in the heated plunge pool – everything was a dream. The kitchen was fully stocked with everything you need- and the local grocery store is a short drive away! So many fantastic restaurants nearby to try. Going out for day trips to nearby towns was also straightforward. Coming back to relax and lounge by the pool was the perfect way to end the day! There’s something special about Isola Serena – you simply feel happy and calm once you step foot onto the property. Kudos to Natalia the property manager being so responsive, professional and helpful. For an extra special meal and experience, we highly recommend a private dinner and pasta making class with Paola. Thank you Isola Serena for being the perfect paradise escape for our entire family to enjoy!

Alex L.

Absolutely Incredible.

We had a dream getaway at Isola Serena. From the moment we arrived, we were blown away but the uniquely Italian character and breathtaking Tuscany views, with modern amenities for that extra level of comfort. Each of the six large bedrooms has its own ensuite washroom so no fighting over who gets which room, they’re all great! The kitchen is spacious for cooking large family meals and has a dishwasher to help with quick clean up. Or not into cooking on vacation, the hosts helped organize our own personal chef – what a treat! The large patio and pool looks out on the classic Tuscan view of endless rolling hills of vineyards and olive groves and the large patio table is perfect spot to enjoy a feast with family and friends – everyone will fit! It’s also less then a 10 minute drive into town to pickup fresh food from the market and visit the local shops. From there your in central Tuscany so it’s a quick drive to explore the unique neighbouring towns or go into Siena or even Florence where you can stop in at places like The Mall for some great designer shopping. I can’t say enough about how much our family enjoyed our stay other then, we can’t wait to be back! So many more hidden gems to explore. Thank you Serena and Peter for making our stay one to remember.

Jesica S.

Fantastic Week at Villa Isola Serena

We looked at many properties, both online and during a December visit to Chianti. This villa was by far best location we found. Everything was perfect, from our communication with Serena, to the reception by Raffaella, and then a stay in an amazing villa in an amazing setting. We were a group of maximum 9 persons, ranging in age from 20 to 60, and all were pleased with the amenities, especially watching the sunset across the vineyards and hills of Tuscany from the terrace. We will be looking to come back, maybe in the fall when the grapes have been picked and the tourists have all left for home. Bravo!

James A.

Planning a trip to Tuscany?

Escape to the heart of the Tuscan countryside for an exceptional stay and experience. Bask in the charm and breathtaking views that await you at our luxurious villa.

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