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Villa holiday rentals in Greve in Chianti

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Popular amenities for villa rentals in Greve in Chianti

Private villa rentals

Guest favourite
Villa in Palaia
5 out of 5 average rating, 10 reviews

Villa La Gemma

JoshRating, 5 stars3 days ago
I was genuinely impressed by this place. So beautiful! The pool is incredible, they had prosecco and limoncello for us and provided several supplies for a successful stay. I would 100000% come back here!
Top guest favourite
Villa in Poggibonsi
4.93 out of 5 average rating, 45 reviews

Villa with pool in Chianti Area

RickRating, 5 stars5 days 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 favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars1 week 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.
Top guest favourite
Villa in Gaiole in Chianti
4.92 out of 5 average rating, 26 reviews

Sestuccina

ClaireRating, 5 stars3 weeks ago
We spent part of our Honeymoon staying at this beautiful villa and quite honestly, we could not have picked a more perfect place. Check in was quick and easy. We met Luciano’s daughter, Birgitta on site and she talked us through the villa and all nearby amenities we may need. She was extremely kind and helpful. The little village is close by and the villa has everything you need to cater for yourselves and have a completely private get away. We cannot recommend enough. The villa was beautifully clean and the surroundings were stunning.
Guest favourite
Villa in Asciano
4.93 out of 5 average rating, 87 reviews

Casa Bianca, a gorgeous Tuscan home in Crete Senesi

PattiRating, 5 stars2 weeks ago
Spacious, private, well decorated Tuscan villa. Very peaceful yard with beautiful views including a hot tub we enjoyed (not as hot as hot tubs in USA but still relaxing) - kitchen was well stocked also with thoughtful bread eggs and pasta and caffe. Grazie!!
Guest favourite
Villa in Greve in Chianti
4.81 out of 5 average rating, 58 reviews

Beautiful villa in Greve in Chianti

SophieRating, 5 stars3 weeks ago
We had an amazing stay at Roberto's place! The villa was just as described and perfect for a group of 10 - the location was great, lovely and quiet with stunning views from the pool. We would not hesitate to stay here again, thank you Roberto!
Superhost
Villa in Lucca
4.91 out of 5 average rating, 23 reviews

Villa Lina, Luxury Farmhouse with Pool and Amazing

BrookeRating, 5 stars1 month ago
Villa Lina was even more beautiful than the pictures showed. The house was clean, had new and comfortable bedding, had plenty of space for our family, and the view was outstanding. The place is very private, high up on the hill, but with the instructions from our host we had no trouble finding it, even in the dark. The driveway is about 1/4 mile, steep, with parts of it gravel, and has several sharp turns, but we made it no problem with the small jeep we rented (without 4WD). Just take it slow. It is about a 15 minute drive back down to the town center of Lucca and the train station and 10 minutes to a grocery store. The back roads are very narrow until you get to a main road so use caution and we were lucky enough that others backed up for us when we met on the narrow spots. The view and seclusion were well worth the drive up for us. If you want an amazing view of the Tuscan countryside, but also a short drive to a neat town and a train station, Villa Lina is a great choice!
Superhost
Villa in Greve in Chianti
4.83 out of 5 average rating, 30 reviews

Romantic Villa with private pool and fabulous view

WilliamRating, 5 stars1 week ago
This is one of the most beautiful and unforgettable locations we have ever visited. To be able to wake up in a centuries old villa and look out over the hillside with olive groves and vineyards was spectacular. Janine was so helpful to meet us and help us get acclimated and then provide a list with local wineries, restaurants, small towns to visit and things to do. We are so very grateful for her hospitality and ready to book another trip soon. Thank you Janine for everything.

Luxury villa rentals

Top guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 123 reviews

Casale in Val D’Orcia

DanielaRating, 5 stars1 month ago
Absolutely beautiful home! We very much enjoyed our stay and the area of Sarteano. We will be back again!
Top guest favourite
Villa in Barberino Tavarnelle
5 out of 5 average rating, 36 reviews

Valluccia 51

FlorisRating, 5 stars4 weeks ago
We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.
Top guest favourite
Villa in Rignano sull'Arno
5 out of 5 average rating, 14 reviews

villa "La Fonticina"

AmiraliRating, 5 stars3 weeks ago
We had a wonderful stay! The property sits on a stunningly large lot surrounded by trees, which gave it a peaceful and private feel. The pool was a highlight — spacious, clean, and with beautiful views that made every swim feel special. Inside, the decor was tasteful and thoughtfully done, blending comfort with style. Everything was clean and well-maintained. Highly recommend for anyone looking for a relaxing escape in nature without compromising on style!
Top guest favourite
Villa in Monsummano Terme
4.98 out of 5 average rating, 125 reviews

Le Maggioline Your Tuscany country house

SarahRating, 5 stars1 week ago
We had the most wonderful stay at Olga’s place. We had 6 adults and two children and there was still plenty of space. The house was beautifully appointed and the outdoor space with the view was the perfect place to relax.
Top guest favourite
Villa in Montepulciano
5 out of 5 average rating, 48 reviews

Terra Antica Suite & Ville - Montepulciano

JohnRating, 5 stars3 weeks 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.
Top guest favourite
Villa in Monticchiello
4.98 out of 5 average rating, 154 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

MelindaRating, 5 stars3 weeks ago
This was true Tuscany! We enjoyed the quaintness of the village with amazing restaurants and views! Tony transported us to and from the villa! Seamless planning. Deborah arranged transportation for us to visit other villages where we enjoyed the day, people and food! Wished we had more time!!
Guest favourite
Villa in Lastra a Signa
4.98 out of 5 average rating, 60 reviews

"La Falterona" Villa 15 km Florence

DominicRating, 5 stars2 weeks ago
Domizio’s house was the perfect house for our family trip! The house is huge and the pool is stunning. The road in is pretty easy and the house is so secluded yet 5 min drive to the train (20 min to Florence). The one con was the wifi is hit or miss but it wasn’t an issue for the most part. You must stay here if you’re in the area and looking for a house!
Top guest favourite
Villa in Orentano
4.98 out of 5 average rating, 101 reviews

Villa Gourmet Food, Pizza, Chef, Pool and Nature

MikeRating, 5 stars3 weeks ago
We had a wonderful stay at Stefano’s villa, he was incredibly attentive and couldn’t do enough for us. The villa was delightful. The highlight was the Pizza cooking workshop which Stefano arranged, we will remember this evening for a long time. Thank you Stefano for a wonderful stay

Villa rentals with a pool

Top guest favourite
Villa in Barberino Tavarnelle
4.94 out of 5 average rating, 53 reviews

Villa Spoianello, amazing holiday in Chianti.

CashRating, 5 stars4 days ago
We had the most unforgettable stay at this stunning villa in the heart of Tuscany! From the moment we arrived, Anna was the most welcoming and attentive host – she went above and beyond to ensure our stay was seamless and special. The villa itself is picture-perfect, nestled among rolling hills and olive trees, offering a true escape into the Tuscan countryside. One of the absolute highlights of our trip was the incredible private cooking class with Vilma, our chef for the evening. She brought so much warmth, expertise, and joy to the experience – we learned how to make traditional Italian dishes from scratch, and the meal we shared afterward on the terrace was unforgettable. The pool area was a dream – peaceful, beautifully maintained, and the perfect spot to relax after a day of exploring nearby towns like Siena and San Gimignano. We spent hours lounging in the sun, soaking in the views, and enjoying the quiet tranquility of the countryside.
Top guest favourite
Villa in Cortona
5 out of 5 average rating, 75 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

CherieRating, 5 stars4 days ago
Immaculate villa with plenty of space for everyone. Exceeded our expectations. Remote location best for people who have a car however peaceful and very close to drive into town in 10 minutes. Amazing restaurants nearby. Spectacular views. Beautiful pool area. Attentive friendly hosts. Especially beautiful Elmo the dog.
Top guest favourite
Villa in Figline e Incisa Valdarno
5 out of 5 average rating, 18 reviews

Mathis House Best View in Chianti, Exclusive Pool

LaylaRating, 5 stars1 month ago
We were already contacted by Emanuele in advance. He sent us the directions so we can easily find the house. We were very warmly welcomed with regional specialties and wine. The stay was great, we felt very comfortable. During the stay we received a lot of tips regarding food and excursion options from Emanuele. He was very helpful and always available. I'm sure we'll be back.
Top guest favourite
Villa in Poppi
5 out of 5 average rating, 15 reviews

Villa Lux Poggelleri with a unique view of the Casentino

KasperRating, 5 stars1 week ago
We are a family of 5 who had a fantastic stay. The house is huge and very nice and the view is not better. 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!
Guest favourite
Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 63 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

ChrisRating, 5 stars1 week ago
Family loved the villa and pool. The closest village is only a few minutes away and has stunning views. There's a great butcher in town as well.
Guest favourite
Villa in Gaiole in Chianti
4.9 out of 5 average rating, 68 reviews

Podere il Trebbio

PiaRating, 5 stars1 week 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.
Top guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 146 reviews

Tuscan farmhouse with private pool and views

JamieRating, 5 stars1 month ago
Wow! A real retreat nestled in the Tuscan hills. It’s a short drive from everything you need, but well clear of any commotion. The house has everything you could desire for an enjoyable stay. Best to hire a car as taxi services come far and few between. Charly and Ann were very helpful and will facilitate you well. Thanks guys!
Guest favourite
Villa in San Donato
4.85 out of 5 average rating, 48 reviews

Vintage 70s Home in the heart of Chianti

BruceRating, 5 stars4 weeks ago
Amazing! We only stayed two nights but wish we could have stayed 2 weeks! Beautiful home and surroundings but what made it special was the hosts. Wonderful people, I highly recommend!

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