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Villa holiday rentals in Casole d'Elsa

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Popular amenities for Casole d'Elsa villa rentals

Private villa rentals

Guest favourite
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 favourite
Villa in San Gimignano
4.88 out of 5 average rating, 72 reviews

Lilium,delux farmhouse in the chianti hills

CharlotteRating, 5 stars2 weeks ago
We had a fantastic stay at Concetta's beautiful home! The house itself is gorgeous and traditionally Tuscan. It is also in the most incredible scenery and sitting outside and taking in the view was an absolute joy. However, by far the best thing about our stay was Concetta and her husband Paolo. They could not have done more to make us feel more at home and it honestly felt like we were part of the family while we were there (including making us the most incredible meal, which I would strongly recommend you do if you stay!) Their hospitality, helpfulness and warmth made it feel like a true escape and I could not recommend it more.
Top Guest favourite
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 a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Top Guest favourite
Villa in Sinalunga
5 out of 5 average rating, 44 reviews

The twigs

NatalieRating, 5 stars2 weeks ago
Sandrine’s Airbnb was by far the best accommodation we’ve ever experienced—a peaceful paradise nestled in the hills of Tuscany. What made it truly unforgettable, though, was the incredible generosity of our hosts. Sandrine welcomed us with a warm smile and thoughtfully provided delicious food and drink throughout our stay. She also shared wonderful recommendations for places to visit and things to see. It was a true blessing to meet such kindhearted and gracious people. 🙏
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 People - Private Pool

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.
Top Guest favourite
Villa in Cavriglia
4.99 out of 5 average rating, 133 reviews

Villa Poggio in Mandria in Chianti

VaughnRating, 5 stars1 week ago
A beautiful place, beautiful surroundings, great hosts, great pool, just everything was perfect. Didn’t want to leave. Felt like home and couldn’t wait to get back there on the days we ventured out.
Guest favourite
Villa in San Gimignano
4.93 out of 5 average rating, 61 reviews

Fabulous 3Br Villa with 360° Views!

EileenRating, 5 stars8 months ago
Cristiana’s home is lovely and just as described. It would be a great house for a family with kids the set up is perfect for parents and children. The location is perfect for taking day trips through the province or just being lazy. The view of this house can only be described as breathtaking- morning, noon and night. During our stay we had some rain which was actually welcomed. We had a beautiful breakfast and sat with a fire in the lovely the house offers. There was not a thing to want for…Don’t hesitate to put this home on your list of must do’s in Tuscany.
Guest favourite
Villa in Radicondoli
5 out of 5 average rating, 51 reviews

Leo's Romantic House

MarcelRating, 5 stars1 week ago
We had a great week at the Belforte. The accommodation was spacious with many retreats and a great overgrown garden. Everything was very well maintained and the facilities were great. Communication with Leo was always smooth and friendly. We will be happy to come back. 👍🏼

Luxury villa rentals

Top Guest favourite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Top Guest favourite
Villa in Soffiano
5 out of 5 average rating, 39 reviews

Charming villa 15' walk to center stunning view

RuthRating, 5 stars1 week ago
Incredible property with a breath taking view over Florence. Hard to put into words how perfect the property is but the best part of the whole experience was the hospitality Marco, Stefania Grinza Carota and Filippo! The best hosts imaginable made us feel so at home, welcome and a part of the family. Now we want to move to Florence
Top Guest favourite
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 favourite
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 favourite
Villa in Buti
4.96 out of 5 average rating, 46 reviews

Villa sii felice

KristinRating, 5 stars3 days ago
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!
Top Guest favourite
Villa in San Ginese di Compito
4.99 out of 5 average rating, 129 reviews

Farmhouse , pool, 13 px. Lucca 10km

EduardoRating, 5 stars3 months ago
We had an amazing stay at Juri's beautiful villa in Tuscany! The place is super spacious, easily accommodating our group of 11, and it was spotless and very well maintained. Juri and his mom were incredible hosts—always responsive and ready to help whenever we needed anything. The location is also perfect for day trips to Florence, Pisa, and Lucca. If you're looking for a charming, well-kept and very clean villa with top-notch hospitality, this is the place. Highly recommend! Let me know if you'd like any tweaks!
Guest favourite
Villa in Lucignano
4.88 out of 5 average rating, 24 reviews

Unique Villa in Tuscany

KeithRating, 5 stars1 week ago
A stunning property, completely private and quiet. Large outdoor heated pool was well maintained with perfect outdoor eating and sitting areas. We ate out on the terrace every night. Luc recommended the closest Osteria which we all loved, and also recommended the spot to see those iconic views of Tuscany with the avenues of cypress trees. All 6 of us had joyful experience. Highly recommended.
Top Guest favourite
Villa in Gaiole in Chianti
4.98 out of 5 average rating, 49 reviews

Sestuccia

AnnieRating, 5 stars3 weeks ago
This was the most magical place so spend a week in Chianti! The villa is exceptionally beautiful, and has everything you could need for a comfortable stay. The grounds were spectacular, with many things to do and different areas to sit and enjoy. My toddler especially loved picking strawberries from the small garden and collecting eggs from the chickens for breakfast. The hosts were lovely and helpful with any questions we had, and took great care of us. The town of Gaiole in Chianti is very close and with great restaurants and things to do. A perfect spot I can’t recommend highly enough!

Villa rentals with a pool

Guest favourite
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!
Guest favourite
Villa in Gambassi Terme
4.96 out of 5 average rating, 54 reviews

Villa Via Francigena

BettyRating, 5 stars3 days ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top Guest favourite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 50 reviews

The Lazy Oak

JarrettRating, 5 stars2 weeks ago
There are very few times when a stay not only lives up to expectations, but exceeds them. Our stay at the Lazy Oak did just that. There are no adjectives to truly describe the beauty of the villa and the surrounding countryside. Sitting at the infinity pool, looking out over the olive groves before a dinner prepared in house by a Tuscan chef as the sun sets will go down as one of the greatest days of our lives. We visited the nearby town twice for gelato but the truth is we did not want to leave the property! If you are looking for a peaceful quintessential Tuscan vacation in the countryside, look no further than the Lazy Oak. Mario is on property to tend to any needs but keeps to himself unless called upon. We actually loved his company and called him over to talk on multiple occasions…with the help of Google translation of course. Thank you Mario and Alesandro for an unforgettable stay. We hope to see you again in the future.
Superhost
Villa in Murlo
4.94 out of 5 average rating, 17 reviews

Pompana Rustic Charm Casale

ArtemiyRating, 5 stars3 weeks ago
A great place for a retreat to enjoy the nature and the silence. The Airbnb has a fantastic location in the nature. It has everything that you need for a short an long stay. The view from the balcony is just amazing. Would definitely recommend it!
Top Guest favourite
Villa in Montaione
4.96 out of 5 average rating, 25 reviews

Private Villa with semi-Olympic pool and Tennis

JosephineRating, 5 stars4 weeks ago
absolutely amazing!! Francesca made us feel right at home. the place was amazing and we definitely want to come back. the property is beautiful and great if you want to play tennis , ping pong, or swim… super fun. Francesca was so sweet, gave us great recommendations, and helped us with all our questions. She even graciously helped our grandma get a doctor to see her when she sick. 10/10 amazing !
Guest favourite
Villa in Volterra
5 out of 5 average rating, 30 reviews

Detached villa with private pool

YannickRating, 5 stars3 weeks ago
We had a great stay here. The location is excellent, both in terms of the amazing view and how secluded it is, and in terms of how close it is to drive to nearby towns like Volterra and San Gimigniano. The pool and the spacious terrace were the highlights for us, as we wanted to relax and unwind.
Guest favourite
Villa in Radda in Chianti
4.96 out of 5 average rating, 93 reviews

la Balza

AlexRating, 5 stars2 weeks ago
Wonderful farmhouse and experience! Very peaceful! Alessandro invited us to a dinner/wine tasting at his family vineyard. Great and delicious experience! Thanks Alessandro!
Top Guest favourite
Villa in Poggibonsi
4.94 out of 5 average rating, 87 reviews

VILLA TALCIONA

MartynaRating, 5 stars3 weeks ago
The property is beautiful, the pool, garden, and view absolutely amazing! check in was easy as Francesco & Elena live upstairs. we used the house as a "base camp" for our wedding which took place in Poggibonsi and a few family members stayed there additionaly after the wedding. the owners were VERY helpful, resourceful and nice. We could use everything and had the most relaxing time. important to know: 3 beds are in the hallway

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Casole d'Elsa
  6. Villa rentals