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

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Dining
Outdoor pool
Exterior
11 bedrooms, desk, iron/ironing board, travel cot
Outdoor dining

Reviews

10 out of 10
Exceptional

Entire home

11 bedrooms12 bathroomsSleeps 23530 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Castellina in Chianti, Siena
  • Place, Montecalvario
    ‪1 min walk‬
  • Place, City Hall Castellina In Chianti
    ‪3 min walk‬
  • Place, Castellina Fortress
    ‪5 min walk‬
  • Airport, Florence (FLR-Peretola)
    ‪73 min drive‬

Room options

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Exterior
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  • Free Wi-Fi
  • Restaurant
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4.7 out of 5, Exceptional, 209 reviews
The price is €246
includes taxes & fees
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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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.
During your stay at this villa, you're just a quick walk from City Hall Castellina In Chianti. Features include an outdoor pool, a gym and breakfast (surcharge). Enjoy your stay with amenities like free WiFi and a private pool in the villa.
  • Air-conditioned villa with private pool, kitchen and washing machine
  • Free WiFi
  • Breakfast is offered for a fee
  • Take a swim in the outdoor pool
  • Services include a concierge, limo or town car service and babysitting
  • On-site recreation includes a gym and a playground
  • Steps from City Hall Castellina In Chianti and 4 minutes on foot from Castellina Fortress
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views offers its guests an outdoor pool and a fitness centre. A library, a terrace, and barbecue grills are also featured at the family-friendly ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views. The villa can provide concierge services and limo/town car service.

This Castellina in Chianti villa is smoke free.

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Massage
  • Outdoor pool
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transport

  • Limo/town car service
  • Car required
  • Parking on site

Kitchen

  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Kitchenette
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Breakfast available for a fee
  • Chef service
  • Dining table

Bedrooms

  • 11 bedrooms
  • Bedsheets provided

Bathroom

  • 11.5 bathrooms
  • Bidet
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • Library
  • Music library
  • Smart TV with cable/satellite channels
  • Stereo
  • Video games
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Terrace

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Absolutely no smoking inside villa.

Services and conveniences

  • Concierge services
  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • In a rural location
  • In a village
  • In the mountains
  • Near a hospital
  • Near an outlet shopping centre

Things to do

  • Gym
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Swimming nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit

General

  • Composting
  • Comprehensive food waste policy
  • Comprehensive recycling policy
  • Garden
  • Locally-owned and organised tours and activities
  • Unit size: 5,700 square feet
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Rules

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.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

Events allowed: family gatherings and birthday parties

Smoking

Smoking is not permitted

Absolutely no smoking inside villa.

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
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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
Property Registration Number IT052005C2SZJXAFTJ

We should mention

  • All guests (including children) need to be present at check-in to show their government-issued photo ID or passport.
  • On-site cash transactions can't exceed USD 5000, due to national regulations. For more details, please contact the property using information in the booking confirmation.

Property is also known as

Isola Serena New Private Luxury Chianti Pool Stunning Views

Isola Serena New Private Luxury Chianti Pool Stunning Views

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

Reviews

10

Exceptional

Rating 10 - Excellent. 65 out of 65 reviews
Rating 8 - Good. 0 out of 65 reviews
Rating 6 - Okay. 0 out of 65 reviews
Rating 4 - Poor. 0 out of 65 reviews
Rating 2 - Terrible. 0 out of 65 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Douglas S.

Liked: Cleanliness
All we could have hoped…and more! The place was ‘spectacular’
Stayed 7 nights in Apr 2026

10/10 Excellent

cathy h.

Liked: Cleanliness
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

10/10 Excellent

Annina S.

Liked: Cleanliness
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

10/10 Excellent

Lizzy C.

Liked: Cleanliness
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

10/10 Excellent

Michelle D.

Liked: Cleanliness
Gorgeous property - we had a wonderful stay
Stayed 7 nights in Aug 2025

10/10 Excellent

Michael M.

Liked: Cleanliness
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

10/10 Excellent

Sherry A.

Liked: Cleanliness

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

10/10 Excellent

Sam G.

Liked: Cleanliness

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

10/10 Excellent

Nick R.

Liked: Cleanliness

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

10/10 Excellent

Tim M.

Liked: Cleanliness

Spectacular Everything

As many have said before, Isola Serena is just wonderful. We had a group made up of 10 couples and to a person they were just blown away at the villa and individual accommodations. Everything you need is there including an abundance of stunning views - from morning til dark, the changing light alters the panoramic landscape so that every minute you feels looking at some new and remarkably beautiful. It’s amazing how much time we spent just gazing across the valley. Raffaella took great care of us during our stay and the cleaning crew made sure everything was refreshed mid-week. We mostly used a private chef (Mattisse) for four of the seven nights and it was a god-send as we were often running all day. We did cook one big meal for our last night there and the villa had everything we needed to pull it off. Getting provisions requires a little planning as the market closes from 1:00-4:00p so you have to keep that in mind. I sure hope we have an opportunity to stay again at this wonderful, magical, and majestic villa.
Stayed 7 nights in May 2025

10/10 Excellent

Kenneth M.

Liked: Cleanliness

NA

A+
Stayed 7 nights in Oct 2024

10/10 Excellent

Roberto R.

Liked: Cleanliness

Simply a dream come true

We were a group of 23, ranging from 18-70. We used Isola Serena as our base to take day trips to Florence, Pisa, Lucca, Siena and the location is perfect. The Villa is simply a dream come true. Everything you can read about it is far from what you will experience. The rooms, the kitchen, the pools, and the insane terrace view is one we will never forget. Then the attention from the online booking from the Kalen Property team to the onsite personal attention with Rafaella who was always on top of everything made this perfect. Don’t hunk about it.. book this beautiful Villa and enjoy a Tuscan life! You will remember it forever.. I know we will. Grazie!
Stayed 7 nights in Jul 2024

10/10 Excellent

James A.

Liked: Cleanliness

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

10/10 Excellent

John S., Christchurch

Liked: Cleanliness

Fabulous in Chianti

Great villa - perfect for large family stay
Stayed 7 nights in May 2024

10/10 Excellent

Jaclene F.

Liked: Cleanliness

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!!
Stayed 7 nights in Apr 2024

10/10 Excellent

Ivan L.

Liked: Cleanliness

An unforgettable experience.

Our stay at Isola Serena was an unforgettable experience! The villa was very clean and the private gym and infinity pool are fantastic perks, especially after a day of sightseeing to nearby towns, cities, and vineyards, all of which were in great proximity to the villa. The property is perfect for large groups of families or friends, as every bedroom has an ensuite bathroom and there is 1 main house and 2 guesthouses, so everyone could still have some privacy while still being together. It is also very kid-friendly as the villa has a children's playground and sandbox, so the kids kept themselves busy as well as spent time in the large infinity pool and small plunge pool. The owners were excellent and made booking very easy as they answered all of our questions, gave us many great recommendations, and their onsite local property manager, Raffaella, was great and very attentive, showed us around the entire property, and continuously checked in on us throughout the week. Highly recommended Isola Serena for those seeking a luxurious yet cozy retreat with the full Tuscan experience! We will definitely be back again!
Stayed 7 nights in Mar 2024

10/10 Excellent

Zhuowen Y.

Liked: Cleanliness

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

10/10 Excellent

Robert C.

Liked: Cleanliness

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

10/10 Excellent

Matthew J.

Liked: Cleanliness

Wonderful Week

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

10/10 Excellent

B H.

Liked: Cleanliness

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

10/10 Excellent

Mark K.

Liked: Cleanliness

My take

Loved the view, loved the pool, loved the whole stay.
Stayed 7 nights in Oct 2022

10/10 Excellent

Dave M.

Liked: Cleanliness

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.
Stayed 7 nights in Sep 2022

10/10 Excellent

Rita S.

Liked: Cleanliness

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

10/10 Excellent

Kristin H.

Liked: Cleanliness

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

10/10 Excellent

Jessica P., USA

Liked: Cleanliness

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