Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Top rated by guests
Pool
Fully equipped kitchen
Fully equipped kitchen
Pool
Exterior
review stars
9.8Outstanding
(78 Ratings)
"Deciding to spend our summer holiday under the Tuscan sun at Villasimo was the gift that kept on giving. The pictures for this posting on VRBO, while beautiful, do not do this place justice. We have s..."
Joan P.
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(78 Ratings)

Villa in Tuscany

10 guests · 5 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this villa rental

Welcome to Villa Simo!
Our stone farmhouse sits on a hillside in Chianti, just 15 km from the center of Siena. We invite our guests to relax in the garden, take a walk on our 25 acres of private woods, and take in the view of the Chianti hills from the private pool.
Villa Simo sleeps 10 people in 5 comfortable, spacious bedrooms with exposed wooden beam ceilings and terracotta floors. All the 5 bedrooms have AC.

The pool is for your exclusive use.
Villa Simo has 5 bedrooms, 3 bathrooms, 1 living room, 1 dining room and 1 fully equipped kitchen.

You can make your own pizza and use the working wood burning oven next to the barbecue!
Villa Simo is perfect for families and groups of friends who want to spend a relaxing holiday immersed in a tranquil and peaceful environment.
Unlimited internet WiFi available.

Amenities at Villa with private pool on 25 acres in the heart of Chianti, close to Siena

Non-smoking
Pets allowed
Family friendly

Map of Tuscany


Ratings and reviews

9.8 / 10
Outstanding(78 Ratings)
10 / 10Outstanding·Jul 2025
Deciding to spend our summer holiday under the Tuscan sun at Villasimo was the gift that kept on giving. The pictures for this posting on VRBO, while beautiful, do not do this place justice. We have stayed at other homes in the area before, but this one had the perfect mix.Situated between old live trees and Chianti vineyards, with a pool sitting out on a perch overlooking a valley and hills with villages, ancient castles, vineyards - along with absolute peace and exclusivity - this place was amazing. The view from the pool was like being in a live-painting - the clouds even had personality. We enjoyed evenings watching the dusk settle over the valley from the outdoor patio. Balanced with being secluded, the villa is also near towns, a 5-star hotel with a michelin star restaurant next door, and vineyards for winetasting. The road which we jogged could see views of Siena over the vineyards right from the other side of their hill. Last, but certainly not least, the hosts Cristiano and Simonetta were fantastic. The house was in great condition, had everything we needed, a thorough walk through, welcome treats, and were very attentive. They made sure we had privacy and were able to enjoy our weeks in their family home. Would love to stay here again and recommend it.
10 / 10Outstanding·May 2025
We were 3 adults, and we spent 5 lovely days at the Villa. We loved the house and the surroundings very much!We couldn't stop admiring the view from every window and from the yard. The serenity in the mornings was so calming.The house has a good atmosphere, and we liked the design. The kitchen is well equipped.There is a washing machine which we didn't use (no dryer).There is a lovely swimming pool, but we didn't use it either.There are few steps between each 2 rooms in the house, so we wouldn't recommend it for very young kids or elderly people.2 important things to know:- The road from the main road to the house was in VERY poor condition. This could be very challenging for a 'regular'/low rented car. Luckly, we rented a Jeep.We understood this is not the usual condition of the road but one needs to take it into consideration.- Please note there is an additional fee per electricity and gas consumption. This was not a surprise. But take into account this can sum up to a considerable amount. For us, not spending the daytime there (just nights) it was around 250 Euro for 5 nights. The area is also lovely and there is also much you can do without driving too far:Visiting Siena, Wine tasting in one of the many wineries in the area, Visiting 'Parco sculture di Chianti' which we strongly recommend – it's an open park with sculptures integrated in the natural environment.To summarize: The Villa was a great place to spend our Tuscany vacation and we LOVED it!
10 / 10Outstanding·May 2025
Our family of five stayed here for a week. It was a great place to come back to after day trips to Sienna, Florence, Pisa, Volterra, etc. Super quiet and relaxing. It’s a little bit out of the way, but the extra driving was worth it to us.
10 / 10Outstanding·May 2025
Excellent location to go exploring the Chianti region! Great old villa well away from everything.

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FAQs

Is parking included with this villa?

Parking is not specified as an available amenity at Villa with private pool on 25 acres in the heart of Chianti, close to Siena. For more information, we encourage you to contact the property about where to park.

Is there a pool at this villa?

We didn’t find pool listed as an amenity for this villa. It may be worth double checking if a pool is important for your stay.

Is Villa with private pool on 25 acres in the heart of Chianti, close to Siena pet friendly?

Yes! This villa is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Villa with private pool on 25 acres in the heart of Chianti, close to Siena?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.