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

Family-friendly villa with a fitness center and an outdoor pool

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Exterior
Property grounds
Fridge, microwave, oven, stovetop
11 bedrooms, desk, iron/ironing board, travel crib
Exterior
At ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views, you can look forward to a terrace, a garden, and a playground. Treat yourself to a massage or other spa services. Stay connected with free in-room WiFi, and guests can find other amenities such as a library and laundry facilities.

Reviews

10 out of 10
Exceptional

Entire home

11 bedrooms12 bathroomsSleeps 23530 sq m

Popular amenities

  • Parking available
  • Dryer
  • Fireplace
  • Breakfast available

Add dates for prices

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.

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Massage
  • Outdoor pool
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transportation

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

Kitchen

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

  • Smoking not allowed
  • Note from host: Absolutely no smoking inside villa.

Services and conveniences

  • Concierge services
  • Housekeeping (limited availability)
  • Iron/ironing board

Location highlights

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

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 organized tours and activities
  • Unit size: 5,700 square feet
  • Water-efficient showers
  • Water-efficient toilets

Similar properties

Exterior
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region
  • Pool
  • Hot Tub
  • Pet friendly
  • Air conditioning
10.0 out of 10, Exceptional, 23 reviews
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in 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

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

Pets not 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

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 there is a carbon monoxide detector on the property
Host has indicated 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
Property Registration Number IT052005C2SZJXAFTJ

We should mention

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 USD 5000, due to national regulations; for further details, please contact the property using information in the booking confirmation
A car is required for transportation to and from this property

Property is also known as

Isola Serena New Private Luxury Chianti Pool Stunning Views
Isola Serena New Private Luxury Chianti Pool Stunning Views

About the neighborhood

Map
Siena, Castellina in Chianti

What's nearby

  • Casa Vinicola Luigi Cecchi - 1 min walk - 0.0 km
  • Montecalvario - 1 min walk - 0.0 km
  • City Hall Castellina In Chianti - 3 min walk - 0.3 km
  • Archaeological Museum of Chianti - 5 min walk - 0.4 km
  • Castellina Fortress - 5 min walk - 0.4 km

Getting around

  • Monteriggioni Badesse Station - 14 min drive
  • Florence Airport, Peretola (FLR) - 67 min drive

Restaurants

  • ‪Riserva di Fizzano Hotel Castellina in Chianti - ‬11 min drive
  • ‪Bar Brancaia - ‬1 min walk
  • ‪Ristorante Albergaccio di Castellina - ‬4 min walk
  • ‪Il Cantuccio - ‬4 min walk
  • ‪Lo sdrucciolo - ‬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?

Onsite 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?

Check-out 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 Casa Vinicola Luigi Cecchi, Castellina Fortress, and City Hall Castellina In Chianti. Archaeological Museum of Chianti is 0.2 mi (0.4 km) away.

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Reviews

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

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 64 out of 64 reviews
Rating 8 - Good. 0 out of 64 reviews
Rating 6 - Okay. 0 out of 64 reviews
Rating 4 - Poor. 0 out of 64 reviews
Rating 2 - Terrible. 0 out of 64 reviews

Reviews

10/10 Excellent

Jochem G.

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

10/10 Excellent

John S.

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

Fabulous in Chianti

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

10/10 Excellent

Michael M.

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

10/10 Excellent

Sam G.

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

10/10 Excellent

Sherry A.

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

10/10 Excellent

Ashley M.

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

Amazing Stay and Experience at Isola Serena!!

This was a trip we soon won't forget and we will 100% be back to visit. We <3 Isola Serena!!
Stayed 2 nights in Apr 2022

10/10 Excellent

Søren Z.

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

10/10 Excellent

Matthew J.

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

10/10 Excellent

Mark K.

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

10/10 Excellent

Rita S.

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

10/10 Excellent

B H.

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

10/10 Excellent

Ann V.

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

10/10 Excellent

Kristin H.

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

10/10 Excellent

Tim M.

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

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

Jessica P., USA

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

10/10 Excellent

Robert C.

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

10/10 Excellent

Geoffrey C.

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

10/10 Excellent

James A.

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

10/10 Excellent

Kurankye S.

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

10/10 Excellent

Roberto R.

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

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

Zhuowen Y.

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

10/10 Excellent

Alex L.

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

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!
Stayed 9 nights in Jul 2022

10/10 Excellent

Ivan L.

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

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

Jessica P.

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

DREAM VACATION - Paradise in the heart of Chinati

My stay with my family at Isola Serena, was nothing short of incredible. Our time there was a dream, that will continue to return to us forever. The Hosts Serena and Peter, as well as the Property Manager are lovely people. They were extremely helpful in assisting me with organizing my stay. Everything from getting to and from the villa, chefs, wine tours, activities etc. The villa itself was extremely clean, and welcoming. It truly felt like home. The pictures really do not do this property justice. The views from the terrace and the pool are absolutely breathtaking. So magnificent, that we often felt there was no need to leave the property. However, if we felt like getting out. Castellina in Chianti, is a short 10 minute drive from the villa. This allowed for easy and frequent day trips to markets and gelato for the kids. Everyone had their own space, with large bedrooms and ensuites, it felt like a mini hotel of our own. I can not wait to return! Until Next time! Ciao!
Stayed 2 nights in Apr 2022

10/10 Excellent

Jesica S.

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

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.
Stayed 1 night in Apr 2022