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ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

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A large stone house with a swimming pool and outdoor seating area, surrounded by hills and trees.
A large stone house with multiple rooms and a swimming pool, surrounded by forested hills.
A wicker outdoor seating area with a stone wall backdrop and a scenic view of rolling hills.
A dining area with a table set for two, a chandelier, and a view of the countryside.
A spacious living room with a beige sofa, a wooden coffee table, and a vase of flowers. Large windows provide a view of the outdoors.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Castellina Fortress

Popular amenities

  • Balcony
  • Massages in spa
  • Limo or town car service available
  • Kitchenette
  • Private pool
  • On-site fitness centre

Explore the area

View in a map
Castellina in Chianti, Siena
  • Place, City Hall Castellina In Chianti
    ‪3 min walk‬
  • Place, Castellina Fortress
    ‪5 min walk‬
  • Place, Archaeological Museum of Chianti
    ‪5 min walk‬
  • Airport, Florence (FLR-Peretola)
    ‪65 min drive‬

Rooms & beds

11 bedrooms (sleeps 23)

Bedroom 1 - Main House, 2nd Floor, Master

1 King Bed

Bedroom 2 - Main House, 2nd Floor

1 King Bed

Bedroom 3 - Main House, 2nd Floor

1 King Bed

Bedroom 4 - Main House, 2nd Floor

1 King Bed

Bedroom 5 - Main House, 2nd Floor, with balcony and extra twin bed

1 King Bed and 1 Single Bed

Bedroom 6 - Main House, Main Floor

1 King Bed

Bedroom 7 - Guesthouse 1, bedroom with kitchenette

1 King Bed

Bedroom 8 - Guesthouse 1

1 King Bed

Bedroom 9 - Guesthouse 2, guesthouse with 2 bedrooms and kitchen

1 King Bed

Bedroom 10 - Guesthouse 2, guesthouse with 2 bedrooms and kitchen

1 King Bed

Library - Main House, Main Floor with pullout sofa (king bed)

1 King Bed

11 bathrooms, 1 half bathroom

Bathroom 1 - Main House, 2nd Floor, Master ensuite

Towels provided · Bathtub · Bidet · Toilet · Shower only · Hair dryer

Bathroom 2 - Main House, 2nd Floor, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3 - Main House, 2nd Floor, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 4 - Main House, 2nd Floor, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 5 - Main House, 2nd Floor, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 6 - Main House, Main Floor, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 7 - Guesthouse 1, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 8 - Guesthouse 1, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 9 - Guesthouse 2, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 10 - Guesthouse 2, ensuite

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 11 - Main Floor, Powder Room

Soap · Towels provided · Toilet

Bathroom 12 - Infinity Pool

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Kitchenette
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

Add dates for prices

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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 Lilliano Estate Winery and Casa Emma. 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 mountain biking, horse riding and mountain climbing.
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Map
Castellina in Chianti, Siena

What's nearby

  • Montecalvario - 1 min walk - 0.0 km
  • 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 Brancaia - ‬1 min walk
  • ‪Chianti Bar - ‬4 min walk
  • ‪La Perla Del Palazzo Ristorante - ‬11 min drive
  • ‪Fondaccio - ‬5 min walk
  • ‪La Cantina Di Colle Bereto - ‬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.

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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 69 out of 69 reviews
Rating 8 - Good. 0 out of 69 reviews
Rating 6 - Okay. 0 out of 69 reviews
Rating 4 - Poor. 0 out of 69 reviews
Rating 2 - Terrible. 0 out of 69 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Gorgeous property - we had a wonderful stay
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Isola Serena is truly a magical place. We stayed here with 15 friends to celebrate my husband Bryan’s 50th birthday, and it could not have been a more perfect setting for such a special occasion.The villa is majestic, incredibly spacious and beautifully appointed. Every couple had the privacy of their own bedroom and bathroom, while the generous shared spaces made it easy for everyone to gather and enjoy time together.The property itself is spectacular. The patio quickly became our favourite place to sit with a glass of wine and watch the most beautiful Tuscan sunsets, and the pool was the perfect place to spend a lazy afternoon.We also followed Serena’s recommendations and hired a local pizza maker one evening, which was such a fun and memorable experience. We also had a chef come to the villa twice, once for dinner and once for a beautiful lazy day brunch. Both meals were absolutely spectacular especially the lasagna at brunch.The location is ideal for exploring the best of Tuscany, while still feeling completely private and peaceful. Castellina di Chianti is a local gem.Serena and her entire team were wonderful, and a very special mention must go to Raffaella, the house manager, who was warm, helpful and incredibly attentive throughout our stay.Isola Serena gave us memories we will treasure forever. We would return without hesitation to enjoy this extraordinary villa again and discover even more of the hidden gems in this beautiful corner of Tuscany.
Stayed 7 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this outstanding villa and its guest houses near the lovely town of Castellina in Chianti in Italy. The property is over-the-top beautiful, with buildings and outdoor spaces that embrace the sloping terrain. Every addition and renovation feels thoughtful and lovingly done. The quality of everything is of the highest quality. Nothing was cheaply done!Our group of 18 had plenty of room and never felt cramped. We made full use of the expansive pool, cabanas, more than enough chaises and chairs on many decks, top tier huge umbrellas, as well as the two barbecues and pizza oven. There was space to gather and enjoy one another’s company, with separate living areas when we wanted a quieter moment. The main kitchen was all well stocked for at least 25 people. It had 2 frigs and 2 freezers. They even had some oil, salt, coffee, etc supplies to get started. There were washer and dryers in each building along with the bar area. The photos don’t fully show the newer improvements to the property. There is now an enclosed bar by the pool with glasses and dishes to serve 25 people. An addition to guest house #2 has also created two separate living spaces with bedrooms. The 5 new cabanas by the pool were of highest quality and they had lovely soft cushions. The manager, Raefela was just amazing! Always there to answer or to help.I know you will enjoy this fantastic place as much as we did! It is the most private place we have ever stayed at.
Stayed 14 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous in Chianti

Great villa - perfect for large family stay
Stayed 7 nights in May 2024
Response from VrboOwner on 23 Jul, 2024
Thanks so much, John! We hope to welcome you back to Tuscan paradise again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magical!

We had a company retreat at this amazing location. Everyone was in love with the place and the facilities!
Stayed 7 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Week

Better than the pictures. A fantastic view, and the location suited our family group very well.
Stayed 7 nights in May 2023
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy

Wonderful villa

We can highly recommend this villa. Well placed close to a charming little village, nice bedrooms and living rooms, a great pool and a fantastic view. A wonderful place for a big group of people, in our case our entire family. The local host, Rafaella, is very helpfull and nice.
Stayed 7 nights in Jul 2024
Response from VrboOwner on 23 Jul, 2024
Thanks so much, Soren! So wonderful to hear you had a great time with your entire family! We hope to welcome you back to Tuscan paradise again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

My take

Loved the view, loved the pool, loved the whole stay.
Stayed 7 nights in Oct 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Mark! We hope to welcome you back to Isola Serena one day soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spectacular views

Fantastic private location lends to day trips to various towns and wineries. The villa is amazing-ample space for dining and relaxing. Breathtaking views both day and night. Sunsets are stunning. Carefree stay was facilitated by the property manager. We felt like we were home.
Stayed 7 nights in Sep 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Rita, and we hope to welcome you back to Tuscan paradise again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Perfect Tuscan Oasis

Our stay for my mother’s milestone birthday was everything we could have asked for and more. The property was stunning, comfortable, spacious, and was equipped with every amenity one could think of. Raffaella the property manager was so communicative and incredible. She helped with recommendations, was so prompt with answering any questions, and even delivered wine to us during the national holiday when the shops were closed. The kids and adults had the vacation of their dreams, and I know we’ll be back again!
Stayed 7 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Isola Serena

Great villa. Stunning window and outdoor patio hilltop views of Tuscan countryside. Minor issue with heat that property manager alleviated. Definitely hope to return.
Stayed 7 nights in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional Villa for Business Group

As CEO of a boutique professional services firm, I rented this villa for my leadership team and their spouses. It was ideal with 6 bedrooms all with ensuite bathrooms. Every detail was covered flawlessly.
Stayed 7 nights in Sep 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful retreat in heart of Tuscany

What a truly amazing experience! The house, with its views and central location made for an unforgettable stay in Tuscany. The house has everything you need and the new pool is stunning. The property manager, Natalia is extremely attentive and helpful throughout the stay. We cannot wait to book our next trip to Chianti! Grazie Mille Isola Serena!
Stayed 7 nights in Aug 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Kristin, and we hope to welcome you back to Tuscan paradise again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Large home with beautiful views

Our group had a wonderful stay at Isola Serena. The views are amazing and the house is well stocked with everything needed. The pools are lovely and kids enjoyed swimming. We can’t say enough good things about the house manager, Natalia. She helped us many times with dinner reservations, recommendations and made sure we knew to get groceries as things are closed sundays. She is one of the best managers we’ve encountered in our travels! We highly recommend this house for a big group.
Stayed 7 nights in Aug 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Jessica, and we hope to welcome you back to Tuscan paradise again soon! So glad Natalia was so helpful and we've ensured we've passed along your kind words - she is truly amazing!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a Way to Relax!

Isola Serena is a hidden gem between Florence and Siena and many other beautiful Tuscan towns and wineries in between. The Villa is very private and immaculate in every respect - lots of space, modern, yet with an old Tuscan farm-like appeal. And the views? Absolutely amazing. Personally, I would look no further if you want a true Tuscany Villa adventure all your own.
Stayed 7 nights in Jun 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Geoffrey, we hope to welcome you back to Isola Serena again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding and Family Holiday

We had booked the villa for our wedding week to host 23 of our closest friends and family. It exceeded expectations in everyway, the views are breathtaking, the outside living areas are perfect for hosting large lunches and dinners, all the rooms are beautiful, and Raffaella and her team made sure we had everything we needed and more during our stay. It is so peaceful and quiet to enjoy the true beauty of Tuscany but also so close to the local town for dinners and shopping. The list of recommendations was really helpful during our stay. I would 100% recommend holidaying at Isola Serena - you will.not be disappointed. We will definitely be back again
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful villa

The pictures do not do the villa justice. The views from the villa’s terrace, infinity pool deck and splurge pool patio are all amazing…looking over the Tuscan countryside. Spectacular sunsets too. The interior is nicely decorated and perfect for our group of 9 adults. Each bedroom has its own ensuite and all are spacious. The house manager Natalia is very responsive - even to an urgent maintenance issue. We will definitely be back!
Stayed 7 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the most fabulous stay at Isola Serena! Our group of 10 adults and 9 children fit comfortably, with plenty of indoor space and beautiful outdoor areas. The 20m infinity pool was a highlight for both swimming lengths and kids’ games, while the large hot pool was the perfect spot to relax and watch the sunset.The kitchen was spacious and well equipped for cooking big family meals, and we loved dining outdoors or using the excellent BBQ area. Evenings indoors were cozy, with lots of comfy seating for everyone.The villa is comfortable, well equipped, and set in a stunningly peaceful location. Nearby villages have wonderful restaurants, gelato, and shops, with Siena just 30 minutes away and Florence airport under an hour.Communication with the owner and manager was excellent — they truly cared about making our holiday perfect.A fantastic villa for large groups and families! We’d return in a heartbeat!
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tuscan Delights for the whole Family

From our greeting on arrival by Raffealla and her team, we found the impeccable spaces and glorious Tuscan views a feast for the eyes.Accomodations were all clean, well-appointed, and as-advertised. (Some in our group found the beds firm, so be aware if you need a lot of cushion.Every suggestion, from drivers to chefs and photographer, was an introduction to another lovely, highly qualified professional. Inquiries were responded to promptly, and always with such warmth.We are each so thankful to have experienced Isola Serena, and I believe you will be delighted if you have an opportunity to visit this special place.Grazie mallie!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Isola Serena Review

The villa property is more stunning than the pictures indicates. Ensuite bathrooms in every bedroom makes for a great spot with larger groups. The short drive to the centre of Castellina in Chianti and other surrounding Tuscany towns was great. We can't say enough about the pool. Wow! The property manager Natalia was very responsive and was quite helpful in securing drivers and restaurants reservations. We'll be back! Ciao!
Stayed 7 nights in May 2022
Response from VrboOwner on 21 Sept, 2023
Thanks so much Kurankye, we hope to welcome you back to Tuscan paradise again soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in May 2024
Response from VrboOwner on 23 Jul, 2024
Thanks so much, James! It's so wonderful to hear you all had a great time! The Tuscan sunsets will be waiting for your return and we hope to welcome you back to Tuscan paradise in the fall!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Isola Serena is truly a special corner of the world. For two weeks, our extended family of 22 spread out comfortably across the main house and two beautifully appointed cottages and enjoyed the showstopping infinity pool and breathtaking views of the Chianti hills. There were wonderful surprises around every corner, from the pollinator and fresh herb gardens to the walking trails around the property. The attention to detail the owners have taken, and the love they have for Isola Serena, is evident. From the booking process through the end of our stay, they were responsive to our every request, and words cannot express our appreciation for our new friend, Raffaella, who went above and beyond to make sure we were comfortable during our entire stay. Thank you for allowing us to share and experience your slice of Tuscan paradise.
Stayed 14 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We celebrated our honeymoon with our friends in this amazing villa. The Check In process & contacting the property manager was super easy. Half way through the week there was a change of towels and they even took some of the garbage with them (as the disposal was not easily accessible. The road to the villa is a bit adventurous, but all guests with all types if cars were able to make it to the villa. The many outdoor spaces are perfect for larger groups and thanks to the three seperate houses (all equipped with their own kitchen) each group has the option to retreat and have some time to themselves. Unfortunately the Jacuzzi was broken during our stay, this would have been nice for the cooler september nights. All in all we had an amazing stay! We hope to come back again maybe as our 5 year anniversary :).
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Most beautiful villa for our family for a big birthday. I wanted a fabulous outdoor patio dining table that could manage our group of 12 over looking views and vineyards. I wanted comfortable updated bathrooms, bedrooms for all guests with air conditioning. I wanted a dreamy pool experience sipping wine laying out at the pool while looking out magical views. I wanted a villa close to a village where we could go grocery shopping and dinners. This all came true in this most incredible villa. We hired a chef for one dinner, a family cooking class another night and brought in the pizza chef another night … all a 10!! I researched for 6 months to find the best villa. Isola Serena was all I dreamed of and more! We have never witnessed more beautiful sunsets. Rafaella was fabulous always available to help with reservations and anything you need. This place is magical!
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Stay

Isola Serena is just a dream come true for anyone seeking a slice of Italian paradise! We were blown away by the panoramic view of the Tuscan countryside – the pictures just don’t do it justice! We stayed in the guest house, Casa Oliviero, and it has one of the best views overlooking the beautiful large infinity pool and vineyards. The other guesthouse, Casa Matteo, was furnished with Italian style windows and doors that also made it super charming. We spent most of our time relaxing at the villa and the infinity pool was perfect for lounging and soaking up the sun. Our group also loved the location of the villa and how convenient it was to pick up groceries and supplies at the local town, Castellina in Chianti, which has everything that you need, including a great grocery store, restaurants, cafes, shops, gelato, and wine tasting. It was a week we'll never forget, and we can’t wait to be back again with a drink in our hands watching the sunset behind the rolling Tuscan hills every night!
Stayed 7 nights in Mar 2024
Response from VrboOwner on 23 Jul, 2024
Thanks so much, Zhuowen! So glad to hear you all had a great time! We hope to welcome you back to Tuscan paradise again soon!
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