
Villa vacation rentals in Civitella in Val di Chiana
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Top-rated villa rentals in Civitella in Val di Chiana
Guests agree: these villas are highly rated for location, cleanliness, and more.
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Popular amenities for Civitella in Val di Chiana villa rentals
Private villa rentals

Casanova of Bricciano
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.

Villa Il Tollino
We had a wonderful stay at this place! Ginacarlo and Gabriella are extremely friendly hosts who have a lot of helpful recommendations and are always very responsive. Moreover, they not only brought us homemade pizza, sweet treats, fruits and wine, they also brought toys for our 1.5year old daughter! The home is clean and has everything you need for your stay. The views from the patio of the surroundings are amazing!! The entire area is also very peaceful and relaxing and close to many interesting locations (Siena, Arezzo, Montepulciano etc). We highly recommend this place and would come back again!

Casa Bianca, a gorgeous Tuscan home in Crete Senesi
Photos do not do justice to the amazing views. Very special place.

Villa Lux Poggelleri with a unique view of the Casentino
We are a family of 5 who had a fantastic stay. The house is huge and very nice and the view is unbeatable. All stress leaves the body when you are there. Everywhere you looked, there were exceptionally beautiful views. In addition, Lucia and Frederico were so warm people and made us feel very welcome. We will definitely be back!

CHARMING VILLA IN CHIANTI
When you think of a quiet, beautiful place to rest and with all the amenities… this place fits perfectly!! Great breakfasts and everything homemade!! Finally, I'd like to highlight their kindness and know-how… a 10!!

Montemarcoli
We had an amazing stay at the villa. A modern house in quiet surroundings with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.

Terra Antica Suite & Ville - Montepulciano
Beautiful property. Staff were amazing, responsive and friendly. Location ideal for visiting other cities by car. Exactly as pictured. Breakfast which was added on a day to day basis was spectacular. Very relaxing sitting on patio and by the pool.

Villa Fortuna with Hot-Tub and pool near Tuscany
A Perfect Holiday – Like Heaven on Earth! This place exceeded all our expectations. A stunning and peaceful location with breathtaking views over the valley, lake, and mountains. The house and garden were beautifully maintained, and the accommodation was very clean and comfortable. A special thank you to Mrs. Lesley, who was an invaluable help throughout our stay. She provided us with plenty of useful tips and advice on various matters, such as train tickets and local attractions. Thanks to her, we were also able to arrange a wonderful dinner at the villa – truly an unforgettable experience. We wholeheartedly recommend this place – if we could give it 150%, we absolutely would!
Luxury villa rentals

Agriturismo il Friscello, your natural pool
Truly beautiful home. Majestic, mystical and refined. Our kids loved the river and had a blast in the gardens. Thank you Ginevra for a wonderful weekend getaway.

Villa with pool in Chianti Area
Our stay at Mariella's beautiful home was a highlight of our five week trip throughout Italy. Peacefully situated between Florence and Siena, this villa offers a welcoming respite from the hustle and bustle of the cities. It was also super convenient to the vineyards throughout Chianti. Waking up every morning to the sunrise views over the valley and enjoying a glass of wine in the evening were the perfect beginning and ending to each day. The pool was even larger than we imagined and provided days of entertainment sprinkled in during a week of sightseeing and wine tasting. I cannot recommend this home, location, or host enough. You will NOT be disappointed!

Wp Relais Borgo Vignalunga
We had a lovely stay — the villa is absolutely beautiful and we had a great time enjoying the space and surroundings. The location is also ideal, close to stunning towns like Pienza. A few improvement points: there was no proper coffee-making equipment, just a few filters; the fireplace hadn’t been cleaned and had no firelighters; and the air conditioning didn’t work in about half the rooms. Also, the check-in wasn’t smooth — the time was moved to 16:00, but the cleaners were still busy when all 14 of us arrived. With a bit more attention to these details, it could be a truly exceptional stay.

Charming villa 15' walk to center stunning view
Wonderful villa with a beautiful outdoor area- fruit trees, roses, and flowers. We enjoyed the wine, snacks and fresh fruit the host had for us upon arrival. This was our last stop in Italy. Bedding, mattresses and AC has not been great in the places that we have stayed, and never was there a fan. This villa had a comfortable bed , great ac, and a ceiling fan in the bedroom. My husband said his best night sleep the entire trip. We were missing our dogs and cats and we loved having theirs visit us daily! The hosts were traveling so we didn’t get the chance to meet them. They regularly checked in on us to make sure everything was good and provided local recommendations. Given the reviews and accommodation, I’m sure they are amazing! If you’re ever in Florence, this place is worth the stay.

Villa in Montepulciano with a Pool
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!

The Lazy Oak
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!

Villa with garden. The Cardinal's Garden.
Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.

Tuscany Country House with swimming pool
Cannot say enough about the gracious, responsive hosts. The location has a beautiful view, amazing places to sit and converse, super sleeping arrangements for a large group like ours, just a wonderful place to spend two weeks.
Villa rentals with a pool

Private villa with pool
Very friendly hosts, clean house, and perfect view. Everyone was very pleased with the stay and would recommend it highly!

Fabulous Farmhouse with Pool & 360 Panoramic View
Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!

Bellagatta, an Enchanting spot in Val d'Orcia
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!

Elegant Chianti Villa w/ Stunning Views + Starlink
We’ve visited many places in Tuscany over the years, but this villa truly stood out as one of the best-equipped homes we’ve stayed in. From the kitchen to the little day-to-day essentials, everything was there — it felt less like a rental and more like a very comfortable home-away-from-home. The space was more than enough for our group of five adults and one baby. There’s even a cellar that could easily accommodate a few extra people if needed. The house is beautifully maintained and spotlessly clean — the cleaning team really does a great job. The surroundings were wonderfully peaceful and serene, just the kind of setting that makes you take a deep breath and immediately relax. Evenings on the terrace were a highlight for us — we could enjoy a drink and a good conversation while the baby slept undisturbed inside. What you see in the photos is exactly what you get — no surprises, just a beautiful, quiet, well-kept villa. Gino, the owner, was kind and helpful.

villa "La Fonticina"
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.

Beautiful tuscan country house
The house is beautiful and very big. It is located just outside of Buonconvento and offers complete privacy. A car is an advantage. The rooms are spacious, there are mosquito nets above all beds and enough bathrooms and toilets for everyone. In general, the house is very well equipped, both in the kitchen and otherwise. The pool is slightly elevated, beautiful, large, with natural shade all around and offers a magnificent view on the surrounding countryside. In the huge garden you can eat, linger, play... There is even a small basketball court. But beware: right next door there are wild blackberries and the ball can be lost :) In Buonconvento there is a coop, a fine gelateria and a good coffee with the famous and fine products of Le Dolcezze di Nanni. For a good pizza, the drive to the Mulinum restaurant is worth it a little outside, they have their own mill and process their own grain. We highly recommend the house.

Podere il Trebbio
We - a family of seven adults - had a really great stay at Bernardino's house. The house itself was very cosy and charming and contained everything we needed. The pool and the pool area, to which only we had access, was a fantastic extra asset which we enjoyed a lot. The nearby surroundings were also very nice with vineyards and woods. We even spotted three seldom orchids and heard the pirol bird which is very exotic to us. At the same time, it was possible to walk to the nearby town of Gaiole in Chianti where many nice restaurants and cafes can be found.

Villa Cristina Tuscany,your dream!!
Absolutely beautiful property with spectacular views. Wonderful setting for a relaxing holiday. Minutes from town to have morning cappuccino’s. Must visit the Pomaio winery which is a 10 min drive. Leonardo and Marta were so welcoming and taught us so much about their winery.
Quick stats about villa rentals in Civitella in Val di Chiana
Total rentals
50 properties
Nightly prices starting at
R721 ZAR before taxes and fees
Total number of reviews
700 reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- Palazzo Vecchio
- The Boboli Gardens
- Santa Maria della Scala
- Nelson Mandela Forum
- Teatro Tuscanyhall