Villa in Castellina In Chianti
23 guests · 11 bedrooms · 11 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this villa rental
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.
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.
Amenities at ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Non-smoking
No pets allowed
Family friendly
Map of Castellina In Chianti
Ratings and reviews
10.0 / 10.0Outstanding·Sep 2025
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!
10.0 / 10.0Outstanding·Sep 2025
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 :).
10.0 / 10.0Outstanding·Sep 2025
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!
5.0 / 10.0·Nov 2019
I was looking for the perfect villa for a memorable vacation with my grown family (8 adults). Isola Serena checked all of the boxes for me.Centrally located in Castellina di Chianti, a great (not too) little town offering great views, restaurants, wine and some shopping.Castellina is the perfect launching point for regional day trips through central Tuscany as we easily traveled to Florence (north), Siena (south), San Gimingnano (west), Montepulciano (SE), and several other quaint smaller towns and wineries in between. The villa is beautiful, everything as advertised, so much space and privacy for everyone - bedrooms/modern bathrooms/appliances/internet, etc. - again, as advertised and more. The villa has extreme privacy, located at the end of a long, winding dirt road, in the middle of an olive grove and vineyard - just beautiful. For hikers - there is a hiking trail that starts along the driveway road (marked) and ends approx 2 miles later at the villa - perfect for a morning hike.The villa back patio is large with stunning views over the valley, comfortable patio furniture, and is conducive for family togetherness. The patio also has a covered area with a large table for meals and just hanging out for drinking the local wine. The local wine - try them ALL. In restaurants - the house wine is terrific!The check-in and check-out process with Natalia was so easy. She was so accommodating to answer all questions pre-trip and during our stay - easy communication thru What's App.This was a trip of a lifetime.
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Top rated by guests
10.0Outstanding
(64 Ratings)
"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 ..."
cathy h.Don't miss out! Price and availability may change
