Tuscan Villa with private swimming pool

Top rated by guests
Exterior
Dining
Private kitchen
Property grounds
Pool
review stars
9.6Outstanding
(5 Ratings)
Guests enjoyed the spacious pool and rustic charm of the villa, with convenient access to nearby towns and excellent gelato. They appreciated the beautiful surroundings, privacy, and helpful owner.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.6 / 10.0
Outstanding(5 Ratings)

Villa in Castellina in Chianti

8 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

The Cypresses Villa – Elegant Tuscan Retreat with Private Pool

Located in Castellina in Chianti, in the heart of Tuscany’s famous Chianti wine region, The Cypresses Villa is a beautiful stone-built home that offers the perfect balance between luxury, tradition, and relaxation. Surrounded by rolling green hills, this spacious villa is ideal for guests who love outdoor activities, as well as for those who prefer to stay in and enjoy cooking with fresh local ingredients from the neighborhood markets.

Whether you dream of reading under the cypress trees, soaking in the sun by the private pool, or enjoying a Tuscan meal by the fireplace, this villa offers an unforgettable escape.



Sleeping Area (Upper Level)
• 3 Bedrooms:
• 2 bedrooms with queen-size beds
• 1 bedroom with a double bed
• 1 additional single bed
• 2 Bathrooms:
• 1 en-suite bathroom with a shower
• 1 shared bathroom with both a tub and shower
• Extra Room: A small gym area with a few pieces of equipment (not a fully equipped gym but great for a light workout).



Living & Dining Spaces (Ground Floor)
• Living Room – Cozy space with a working fireplace, perfect for relaxing.
• Reading Room – Features a piano for music lovers.
• Dining Room – Large table for up to eight guests.
• Kitchen – Fully equipped with:
• 6 stove burners, fridge, dishwasher, freezer, oven, utensils, and a large fireplace—great for barbecuing or preparing traditional Tuscan meals.
• Additional Spaces:
• Single bedroom with easy access
• Bathroom & laundry room



Outdoor Spaces & Private Pool
• Front Patio & Terrace – Perfect for relaxing with a glass of Chianti wine, reading a book, or enjoying the Tuscan sun.
• Private Green Area – With tables and chairs for outdoor dining.
• Private Swimming Pool (Freshwater) –
• Size: 4x5 meters, depth 1.2m
• Open from May 15th – October 15th
• Exclusively for villa guests (Note: Previously, guests shared a pool, but a new private pool was added in 2017.)



Additional Amenities

FREE Wi-Fi
FREE Parking (easy parking right in front of the villa)
FREE Access to the Private Pool
BBQ & Outdoor Dining Area
Linens and towels are provided
Heater costs 50 euros per day to pay cash at check-in


Guest Experience & Important Notes
• The villa is perfect for families, small groups of friends, and nature lovers looking for a peaceful, sun-filled retreat.
• Pets are allowed, but must be approved at the time of booking.
• The property is large and green, offering plenty of space for walking, hiking, and enjoying nature.
• The road leading to the villa is a countryside road. It is not ideal for sports cars, but it is easily drivable with a regular car (just drive slowly, especially at night when crossing through the wooded area).
• Wildlife Sightings! It’s not uncommon to spot a deer or a fox while driving through this beautiful rural landscape.

Pool Safety Rules:
• Children and non-self-sufficient persons must not be left unattended at the pool.
• No pets in the water.



Distances from Key Locations
• To Town (Castellina in Chianti): 1.5 km
• To the Airport: 45 km
• To the Beach & Harbor: 85 km
• To the Train Station: 25 km
• To the Motorway: 10 km
• To the Hospital: 25 km
• To the Police Station: 1.5 km





The Cypresses Villa is a peaceful, sunlit, and elegant retreat, offering guests an authentic Tuscan countryside experience. Whether you’re exploring the world-famous Chianti wine region, enjoying homemade Italian meals by the fireplace, or relaxing in the private pool, this home is designed to provide comfort, beauty, and a true taste of Tuscany.

We look forward to welcoming you to this special piece of history and nature!

Amenities at Tuscan Villa with private swimming pool

Pets allowed
Family friendly

Map of Castellina in Chianti


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Ratings and reviews

9.6 / 10.0
Outstanding(5 Ratings)
review starsSummary of reviews
Guests enjoyed the spacious pool and rustic charm of the villa, with convenient access to nearby towns and excellent gelato. They appreciated the beautiful surroundings, privacy, and helpful owner.
From real guest reviews summarized by AI
10.0 / 10.0
Danish-American extended family of 7 had 5 great days at the Villa, we might have needed a minute to adjust to the rustic charm but after that we thoroughly enjoyed our stay. After warm and exhausting days traveling to Siena and Florence, everybody loved playing in the spacious pool, especially if farm dog Leo came to play! House is 5 mins from Castellina, which was a favorite town on the trip, it has everything from great restaurants, fun shopping and world class gelato. It is also just 30 mins from Siena, which (while touristy) was a nice visit. Prepare for rustic charm and don't arrive in darkness, the 3-min dirt road to the Villa is best driven during daylight!
8.0 / 10.0
Authentic Tuscan Rental Property
Authentic Tuscan Rental Property
We recently stayed in Florence and then on a whim decided to search for a property with a little more seclusion. We found this villa close to Castellina in Chianti. The house was a little on the large size for our needs and could easily handle 2 families. The house has a great feel and is authentic to this area. It is not over developed inside but has retained it's character and was an excellent base for our exploration of the region. The realtor was efficient and the owner who lives close by extremely pleasant.
10.0 / 10.0
Piacevole soggiorno
Piacevole soggiorno
Perfetto posto per trascorrere un momento di relax. Luogo incantevole e sistemazione caratterizzata da comfort, pulizia e ordine. Merita ritornarci.
10.0 / 10.0
BEAUTIFUL HOUSE AND PLACE
BEAUTIFUL HOUSE AND PLACE
My family and I spent a week at the house , the house is even better than in the pictures and place is very charming. We had a great vacation in Tuscany and the house was in perfect location to explore around. the owner was there to help if we needed him, and he gave us some good tips. Okay we are used to the city life so I kind of miss all the services , the shops are not 24/7 but that is what you want to find in the Tuscany , right? authentic life.
10.0 / 10.0
Wonderful stay in a wonderful place
Wonderful stay in a wonderful place
I stayed 2 weeks with family and friends and we all fell in love with the place ! Such a large exquisite old house, a lot of inside and outside spaces for each to enjoy some privacy. Loved the quietness, the environment so beautiful and green, the pools so enjoyable. The neighboring village is in my opinion one of the nicest place in Chianti, with plenty shops and good restaurants. Access road is bumpy yes, but really manageable. Last but not least, the owner is a delightful person, helpful, attentive but discreet, wonderful ! We are definitely thinking about returning !

FAQs

Is parking included with this villa?

Parking is not specified as an available amenity at Tuscan Villa with private swimming pool. 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 Tuscan Villa with private swimming pool 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 Tuscan Villa with private swimming pool?

We found 2 amenities for this rental. This includes pets allowed, and family friendly.


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