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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 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.
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.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 25 reviews

Luxury Tuscany Villa on the hill with private pool

EmmaRating, 5 stars3 weeks ago
We booked this for a girls holiday and we had the best week. We didn’t hire a car, we walked to a few of neighbouring towns and got a taxi to Lucca, and a train to Florence one day. Neighbouring towns have small supermarkets and the walks to them were enjoyable, the scenery is truly incredible. Lucca is beautiful and has incredible markets, it’s a must see if you stay here. The villa itself is exactly as shown in the pictures, the pool area is gorgeous, we sat around the table every night for dinner, and when it’s dark there’s clusters of fireflies sparkling in the roses, it was magical. Stefania was great, very responsive and there if we needed her. We’d definitely recommend and book this villa again in the future!
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 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.
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. 🙏
Top Guest favourite
Villa in Monticchiello
4.98 out of 5 average rating, 154 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

MelindaRating, 5 stars4 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!!

Luxury villa rentals

Top Guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Stone farmhouse in Val D'Orcia

Theng JuhRating, 5 stars2 weeks ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
Guest favourite
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 favourite
Villa in Monsummano Terme
4.98 out of 5 average rating, 126 reviews

Le Maggioline Your Tuscany country house

BradleyRating, 5 stars1 week ago
The place was exactly as described. Clean, comfortable and well-equipped. The location was perfect for spending time with the family in a private setting but being close enough to the local town. I’d definitely stay here again and highly recommend it to others!
Guest favourite
Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 64 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

Devon And DavisRating, 5 stars3 days ago
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!
Top Guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars3 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.
Top Guest favourite
Villa in San Leolino
4.99 out of 5 average rating, 109 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

ElkeRating, 5 stars1 week ago
Our stay with Marta and her family could not have been nicer. We felt absolutely comfortable from the first moment. The property is absolutely spacious, lovingly furnished, incredibly well maintained and run with love. Marta and her family are absolutely lovely and take care of their guests very nicely. All wishes are fulfilled. The pizza evening was wonderful and a successful conclusion to our stay. If you are looking for a dreamy, secluded Tuscan ambience and loving hosts, "Poggio del Fattore" is the right place for you.
Guest favourite
Villa in Tignano
4.95 out of 5 average rating, 171 reviews

Villa Isabella

DouglasRating, 5 stars3 weeks ago
The home was located about 1/2 mile from several quaint small towns. Many great restaurants and tours through the beautiful hills and wine country. Very relaxing for family, friends or just to see you unwind by yourself. I highly recommend this location. Take advantage of tours arranged by Nicollo'and his family. We had a ball! Thank you.
Top Guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 148 reviews

Tuscan farmhouse with private pool and views

MelissaRating, 5 stars4 days ago
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann

Villa rentals with a pool

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

Stunning Tuscan Villa & Panoramic Infinity Pool

CherieRating, 5 stars1 week 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.
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 stars5 days ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top Guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 27 reviews

Sestuccina

EmmaRating, 5 stars2 weeks ago
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.
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 Sovicille
5 out of 5 average rating, 16 reviews

TRUE TuscanProperty Exclusive useSiena20P A/C Pool

CelineRating, 5 stars2 weeks ago
A timeless moment. The house is even better than in the photos. Liesbeth and her husband are incredible. We had two meals with them (Tuscan specialties and pizza oven) and we spent two unforgettable evenings, everything was delicious. We were 12 adults and 5 children. We'll be happy to go back!
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!

Destinations to explore

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