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Villa vacation rentals in Civitella in Val di Chiana

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Popular amenities for Civitella in Val di Chiana villa rentals

Private villa rentals

Guest favorite
A charming stone-crafted villa is set among lush greenery, with terraced levels adorned by landscaped gardens. A private pool with sun loungers is positioned in the lower terrace, while the villa overlooks rolling hills, providing a tranquil backdrop for relaxation.
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars2 weeks ago
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.
Guest favorite
A spacious terrace features a stone wall and a round dining table surrounded by several chairs. Potted plants adorn the area, with scenic views of the countryside visible in the background under a partly cloudy sky.
Villa in Scrofiano
4.98 out of 5 average rating, 57 reviews

Villa Il Tollino

MelRating, 5 stars1 week ago
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!
Guest favorite
A shaded outdoor seating area is furnished with comfortable sofas and a stone table, surrounded by lush greenery and colorful potted plants. A hot tub is visible in the background, providing a tranquil setting with views of the picturesque landscape.
Villa in Asciano
4.93 out of 5 average rating, 88 reviews

Casa Bianca, a gorgeous Tuscan home in Crete Senesi

JulieRating, 5 stars1 week ago
Photos do not do justice to the amazing views. Very special place.
Top guest favorite
The exterior of the villa showcases a rustic stone facade under a clear blue sky. A swimming pool is visible in the foreground, with white lounge chairs positioned nearby. A covered patio area features a dining set, providing a welcoming space for outdoor relaxation.
Villa in Poppi
5 out of 5 average rating, 15 reviews

Villa Lux Poggelleri with a unique view of the Casentino

KasperRating, 5 stars2 weeks ago
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!
Superhost
A serene outdoor space features a sparkling pool bordered by a well-maintained lawn and vineyards. Lounge chairs are positioned alongside the pool, and a table is set with snacks and cups, inviting relaxation. A cloudy sky adds depth to the tranquil atmosphere.
Villa in Campogialli
4.68 out of 5 average rating, 25 reviews

CHARMING VILLA IN CHIANTI

LlucRating, 5 stars1 month ago
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!!
Top guest favorite
An outdoor dining area is set with a green stone table, featuring neatly arranged plates, silverware, and glassware. A blue ceramic pot and a bottle of wine are included. The background reveals an infinity pool overlooking a lush forest with rolling hills under a partly cloudy sky.
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars2 weeks ago
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.
Top guest favorite
A modern kitchen area is seen, featuring white cabinetry and a stone backsplash. Kitchen appliances, including a microwave and coffee maker, are visible. A dining table with wooden chairs occupies the corner, while a comfortable sofa is positioned nearby. Warm lighting enhances the inviting atmosphere.
Villa in Montepulciano
5 out of 5 average rating, 48 reviews

Terra Antica Suite & Ville - Montepulciano

JohnRating, 5 stars1 month ago
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.
Guest favorite
An inviting outdoor area features a rectangular pool surrounded by a tiled patio. Lush greenery and flower beds line the space, while a rustic stone house with a tiled roof is visible in the background, completing the tranquil atmosphere.
Villa in Paciano
4.98 out of 5 average rating, 45 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

JenniRating, 5 stars3 weeks ago
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

Top guest favorite
An exterior view of a stone building is showcased, surrounded by lush greenery. A gravel pathway leads to the entrance, where a shaded terrace with sun umbrellas is visible. A weathered wooden table and chairs are positioned in the foreground, inviting relaxation.
Villa in Modine
5 out of 5 average rating, 30 reviews

Agriturismo il Friscello, your natural pool

ChristianRating, 5 stars1 week ago
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.
Top guest favorite
An aerial view captures the expansive countryside, dotted with vineyards and olive groves. The large swimming pool is framed by lush greenery, while the villa's garden offers a serene atmosphere. Gentle hills roll in the background under a clear, blue sky.
Villa in Poggibonsi
4.93 out of 5 average rating, 45 reviews

Villa with pool in Chianti Area

RickRating, 5 stars1 week ago
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!
Guest favorite
A serene outdoor space is presented, featuring a black stone pool surrounded by lush green grass and trees. The villa's rustic structure is visible in the background, with a shaded area provided by a large tree. Sun loungers are positioned nearby for relaxation.
Villa in Castiglione d'Orcia
4.97 out of 5 average rating, 118 reviews

Wp Relais Borgo Vignalunga

SumeRating, 5 stars1 week ago
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.
Top guest favorite
An arch adorned with blooming wisteria frames a lush garden, featuring greenery and vibrant flowers. A terracotta pot sits nearby, while a picturesque tower rises in the background, adding a historic charm to the tranquil outdoor setting.
Villa in Centro Storico
5 out of 5 average rating, 40 reviews

Charming villa 15' walk to center stunning view

ChristineRating, 5 stars1 day ago
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.
Guest favorite
The villa is set against a backdrop of rolling hills and gardens. A large pool is visible in the foreground, featuring a circular shape and steps leading into the water. The stone structure with a tiled roof complements the natural surroundings.
Villa in Montepulciano
4.91 out of 5 average rating, 125 reviews

Villa in Montepulciano with a Pool

SantiagoRating, 5 stars6 days ago
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!
Top guest favorite
An infinity pool sits on a green terrace, surrounded by lush greenery and olive groves. Several loungers are positioned on the lawn, offering views of the expansive valley and distant hills under a clear blue sky.
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars1 week ago
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!
Top guest favorite
The aerial view captures the charming layout of Monticchiello, showcasing terracotta-roofed buildings surrounding a lush green garden adorned with soft lighting. A winding pathway leads to the garden, providing a serene outdoor area amidst the medieval architecture.
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars2 weeks ago
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.
Superhost
The spacious kitchen and dining area features rustic wooden beams and well-lit windows that invite natural light. A large dining table is surrounded by white chairs, accommodating several guests. An inviting seating area with a sofa and decorative elements enhances the communal atmosphere.
Villa in Arezzo
4.94 out of 5 average rating, 51 reviews

Tuscany Country House with swimming pool

VictorRating, 5 stars2 weeks ago
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

Guest favorite
The garden features a swimming pool surrounded by olive trees, offering a picturesque natural setting. Lounge chairs are positioned on the lawn, inviting relaxation. A small stone wall provides a backdrop, while distant greenery completes the serene outdoor atmosphere.
Villa in Monte San Savino
5 out of 5 average rating, 9 reviews

Private villa with pool

DelanoRating, 5 stars1 month ago
Very friendly hosts, clean house, and perfect view. Everyone was very pleased with the stay and would recommend it highly!
Guest favorite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo
4.91 out of 5 average rating, 43 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

Kaidy FendyRating, 5 stars2 weeks ago
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!
Guest favorite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
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!
Superhost
Villa in Castelnuovo Berardenga
4.9 out of 5 average rating, 10 reviews

Elegant Chianti Villa w/ Stunning Views + Starlink

JenniferRating, 5 stars1 week ago
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.
Top guest favorite
An aerial view of a rectangular swimming pool set in a spacious green lawn. Surrounding the pool are six loungers positioned on the stone deck. The tranquil water features steps leading into it, while shaded seating areas are visible in the background.
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars1 week ago
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.
Guest favorite
A rustic Tuscan farmhouse, restored with care, features a tall tower and expansive windows. Surrounding greenery includes cypress trees and shrubs, complementing the natural landscape. The lawn offers open space for relaxation, enhancing the serene atmosphere of the property.
Villa in Buonconvento
5 out of 5 average rating, 11 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
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.
Guest favorite
Villa in Gaiole in Chianti
4.9 out of 5 average rating, 68 reviews

Podere il Trebbio

PiaRating, 5 stars2 weeks ago
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.
Guest favorite
The villa's outdoor area is illuminated under a twilight sky, showcasing a tranquil saltwater pool surrounded by spacious terraces. Comfortable sun loungers are positioned beside the pool, with elegant gazebos visible in the background amidst lush greenery.
Villa in Arezzo
5 out of 5 average rating, 58 reviews

Villa Cristina Tuscany,your dream!!

JaniceRating, 5 stars8 months ago
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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