Villa in Tuscany
14 guests · 7 bedrooms · 7 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this villa rental
Villa Simone is a beautiful stone villa rental in Tuscany dating back to the 15th century. It sits on a panoramic spot in the Chianti hills near San Gimignano.
Built around a watchtower, the villa has been restored in 2023 to preserve its original characteristics. It is furnished in Tuscan style, offers all amenities and can accommodate up to 14 people in 7 bedrooms.
Outside, guests can take advantage of a well-tended garden, private pool with deck chairs and umbrellas, an area for dining outside, and a tennis court: it is the perfect place for a fun, relaxing vacation immersed in the Chianti countryside.
The area is renowned all over the world for its food, wine, art and history. The house is a perfect base for exploring the characteristic villages and art cities of the Chianti and Tuscany, such as Certaldo, Volterra, San Gimignano, Colle Val d’Elsa, Florence, Siena, and Castelfiorentino.
At guests’ disposal: 7 bedrooms; large room with billiard table; private, fully-equipped garden; exclusive use of large swimming pool (16 x 8 m); tennis court; gym and welness area with sauna and Jacuzzi; barbecue; parking within the grounds; panoramic view; wi-fi internet.
Access to the property is via an unpaved road in good condition and suitable for all vehicles.
Distances: San Gimignano with shops of all kinds 5 km, Certaldo 15 km, Volterra 25 km, Siena 40 km, Florence approx. 50 km, Pisa (airport) 75 km.
Please carefully check if there are any extra costs to be paid on site!
===== ACCOMMODATION DESCRIPTION =====
450 m2.
Ground floor: entrance, large hall with dining and living area (Smart TV), billiards room, kitchen (oven, freezer, dishwasher, microwaves, toaster, boiler, wine cooler), store-room with washing machine and dryer, double bedroom with ensuite bathroom with shower, toilet, welness area with sauna and Jacuzzi.
1st floor: 4 double bedroms each with ensuite bathroom with shower, 1 double bedroom with ensuite bathroom with shower (without window), twin-bedded room with ensuite bathrom with shower (without window), gym.
Air conditioning is available in all of the rooms.
The following might be to be paid extra: Babycot, Final Cleaning, Heating, Late Arrival, Pets, Refundable Security Deposit by credit card, Tourist tax.
Built around a watchtower, the villa has been restored in 2023 to preserve its original characteristics. It is furnished in Tuscan style, offers all amenities and can accommodate up to 14 people in 7 bedrooms.
Outside, guests can take advantage of a well-tended garden, private pool with deck chairs and umbrellas, an area for dining outside, and a tennis court: it is the perfect place for a fun, relaxing vacation immersed in the Chianti countryside.
The area is renowned all over the world for its food, wine, art and history. The house is a perfect base for exploring the characteristic villages and art cities of the Chianti and Tuscany, such as Certaldo, Volterra, San Gimignano, Colle Val d’Elsa, Florence, Siena, and Castelfiorentino.
At guests’ disposal: 7 bedrooms; large room with billiard table; private, fully-equipped garden; exclusive use of large swimming pool (16 x 8 m); tennis court; gym and welness area with sauna and Jacuzzi; barbecue; parking within the grounds; panoramic view; wi-fi internet.
Access to the property is via an unpaved road in good condition and suitable for all vehicles.
Distances: San Gimignano with shops of all kinds 5 km, Certaldo 15 km, Volterra 25 km, Siena 40 km, Florence approx. 50 km, Pisa (airport) 75 km.
Please carefully check if there are any extra costs to be paid on site!
===== ACCOMMODATION DESCRIPTION =====
450 m2.
Ground floor: entrance, large hall with dining and living area (Smart TV), billiards room, kitchen (oven, freezer, dishwasher, microwaves, toaster, boiler, wine cooler), store-room with washing machine and dryer, double bedroom with ensuite bathroom with shower, toilet, welness area with sauna and Jacuzzi.
1st floor: 4 double bedroms each with ensuite bathroom with shower, 1 double bedroom with ensuite bathroom with shower (without window), twin-bedded room with ensuite bathrom with shower (without window), gym.
Air conditioning is available in all of the rooms.
The following might be to be paid extra: Babycot, Final Cleaning, Heating, Late Arrival, Pets, Refundable Security Deposit by credit card, Tourist tax.
Amenities at Villa Simone - Luxury Villa with swimming pool
Non-smoking
No pets allowed
Family friendly
Map of Tuscany
Ratings and reviews
10.0 / 10.0Outstanding·Oct 2025
Great for a group - nice mix of charming and updated in good location near quaint San Gimignano. We had some confusion about how to work the soaking tub, but they were responsive and willing to help ( I would recommend some clear signage about what the four valves do versus just verbal instructions on check in). We would have liked access to cleaning supplies like a broom, counter spray, cleaning towels. Some of the bathrooms were out of soap when we arrived. We were able to get most of these things at a store. Overall we would recommend and stay again.
10.0 / 10.0Outstanding·Sep 2025
The Villa was amazing and the pictures matched so expectations were met. Each en-suite bedroom was modern and spacious with well thought out design. There are three different living rooms so people can have their own space if wanted and the grounds are beautiful. Huge pool with plenty of lounging chairs and umbrellas and a very large dining g table inside and outside. The kitchen was equipped with anything needed for cooking, but I would highly recommend the chef you can hire- it’s a husband and wife and their daughter helped two of the nights. They bring everything they need and completely clean up, and they are delightful people. The food was delicious!!
10.0 / 10.0Outstanding·Aug 2025
Wow! This place is incredible, beyond the description and photos. It’s HUGE, so much space, so comfortable for a large group - each bedroom feels like a master, beautiful pool, kitchen, location. Sunsets under the covered verandah - I could have never left. Easy trip to the supermarket and town of San Gimignano. Emma was super helpful. This villa is truly a dream.
10.0 / 10.0Outstanding·Jul 2025
My family of twelve — two grandparents, three daughters, three sons-in-law, and four grandchildren — recently spent a week at Villa Simone. Over the years, we’ve stayed in several villas throughout Italy, each with its own charm, but I suspect our time at Villa Simone will always stand out as our favorite.
The house is perfectly suited for a group like ours, and the grounds are simply stunning. With panoramic views, a large pool, a tennis court, and a pool table, there was always something for everyone to enjoy. The estate produces excellent wines and olive oils, and Posarelli helped us arrange a truffle hunt that delighted all who participated. The grandchildren were especially enchanted by the little dog who found the truffles — which we later ate!
Our time at the villa was effortless and carefree. Emma, the onsite property manager, went above and beyond to ensure we had a truly memorable stay.
Five stars are not enough for Villa Simone. We hope to return — and soon.
$$$$
Top rated by guests
10.0Outstanding
(16 Ratings)
"Great for a group - nice mix of charming and updated in good location near quaint San Gimignano. We had some confusion about how to work the soaking tub, but they were responsive and willing to help..."
Monica M.Don't miss out! Price and availability may change
