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Villa holiday rentals in Casentino

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Casentino

Private villa rentals

Guest favourite
Villa in Pergine Valdarno
4.95 out of 5 average rating, 87 reviews

La Vignaccia (Farmhouse) - villa w/private pool

DominicRating, 5 stars1 month ago
La Vignaccia is wonderful. We were a family of 6 adults plus a baby, and the set up was great for spending time together but also having plenty of space. The kitchen is well equipped for cooking for a large group and the many private spaces were very relaxing. Working remotely was possible with the wifi but not super strong for calls. However there is 5G around the house, so hot spotting from a window worked fine.
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 Ortignano Raggiolo
4.94 out of 5 average rating, 71 reviews

Private Villa with swimming pool in Tuscany

CarrieRating, 5 stars1 month ago
Lacopo was very responsive each time I needed to contact him. The place was very nice but remote. it was about 1 1/2 hours to drive to some of the other medieval cities. It rained a lot but also was beautiful because of the rain. Lacopo and his family were fantastic. The homemade meal his parents prepared for us was absolutely delicious! One of the best meals we had while in Tuscany! It was nice to see how active his parents were and how well they took care of the place. We were surprised to be charged if we used the pool towels. There was nothing mentioned in the description. We would recommend this place. There were 4 adults and we had plenty of room.
Guest favourite
Villa in Casavecchia
5 out of 5 average rating, 28 reviews

Villa "Il Meriggeto"

PicconeRating, 5 stars3 weeks ago
Beautiful weekend, the property allows you to stay in different families with total privacy considering that each room has its own private bathroom. The outdoor area is beautiful and ideal for children, with a hot tub large enough to entertain adults and children. Possibility of super available home chefs to meet different needs (vegetarians, pregnant women), a really pleasant evening. The host was available at all times during the stay, always responding quickly and courteously. In short, highly recommended for a stay with friends or families with children
Guest favourite
Villa in San Gimignano
4.94 out of 5 average rating, 62 reviews

Fabulous 3Br Villa with 360° Views!

BarbaraRating, 5 stars1 month ago
This was my second stay at Cristiana's place and again, it exceeded expectations. The views from the home are pure Tuscany. Christiana is a generous host, providing a fully equipped kitchen, local olive oil to sample while there, and very comfortable, clean living spaces. As a host, Cristiana went above and beyond helping us with a difficult travel situation. She was prompt with her communications, researched solutions for us, and provided resources to help make our stay enjoyable. I can't thank her enough. I hope to return again next year.
Top guest favourite
Villa in Bucine
4.98 out of 5 average rating, 43 reviews

Villa Tontenano Capannole Chianti private pool 12

IndunRating, 5 stars3 weeks ago
This place is fabulous. Margherita was responsive so quickly. We had a 11 people six adults and five kids. Loved the pool and hot tub. Margherita made reservations for us and suggested day trips. She even got a wheelchair for me for the Hill towns. Take advantage of their cooking. they did meals for us, which were fantastic. And even organized a birthday dinner for the three young girls. They did the birthday cake and even gave them a gift. It was fabulous. Don’t hesitate to book. We did day trips to Sienna, pisa,Luca, panzano, pienza and multipulciano. And two trips to the luxury mall.!Her parents are so helpful too. Olive oil and their wine is fantastic. The only regret I have is that we didn’t have extra days and spend the time right around villa. I think we would have really enjoyed the wine tasting and olive tastings. I would’ve stayed easily another week. Do take advantage of her massages too. My kids thoroughly enjoyed our visit. It exceeded my expectations!!!!! Ten stars!!!!!!
Top guest favourite
Villa in Greve in Chianti
5 out of 5 average rating, 47 reviews

Villa Corte - Casine al Sole (Villa Court - Casine al Sole)

EniRating, 5 stars1 month ago
Wonderful villa in Greve, perfect for our large group. Everyone had their own bed and bath and the house was spotless when we checked in. Federico was always willing to answer questions about the house as well as local recommendations and even made us a few reservations. Would 100% stay here again when in Tuscany.
Superhost
Villa in Pierle
4.9 out of 5 average rating, 30 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

HaisamRating, 5 stars2 weeks ago
The villa is located in the heart of the hills, secluded from all the nuisances of today’s world. Check-in was a breeze with extremely straightforward instructions. The host recommended Gimmy for a cooking experience, and that didn’t disappoint. Jackamo was recommended for a trek alongside the property and that too didn’t disappoint. Jackamo was extremely knowledgeable and fun to talk to. To sum it all up, this was one of the most pleasant experiences through Airbnb and we can’t wait to visit again.

Luxury villa rentals

Guest favourite
Villa in Pozzuolo
4.91 out of 5 average rating, 43 reviews

Fabulous Farmhouse with Pool & 360 Panoramic View

Kaidy FendyRating, 5 stars3 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 favourite
Villa in Cortona
4.91 out of 5 average rating, 66 reviews

Villa Le Vigne, 8 pax, private pool, Top Comfort

ChiRating, 5 stars1 month ago
Good host and great communication!
Top guest favourite
Villa in Monticchiello
4.97 out of 5 average rating, 73 reviews

Villa with garden. The Cardinal's Garden.

ShaneRating, 5 stars4 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.
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars9 months ago
Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!
Top guest favourite
Villa in Florence
5 out of 5 average rating, 8 reviews

Florence best view villa Fiaccherella

DimitriosRating, 5 stars3 weeks ago
We booked the place for myself and my wife, my 2 daughters with thei husbands and my 4 grandchildren (aged 2 to 13) and their nunny. We all enjoyed our stay, we all felt we had privacy when we needed, and common areas to be all together. Excellent place for large families or parties. The host ready to answer all questions.
Top guest favourite
Villa in Monticchiello
4.98 out of 5 average rating, 154 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

MelindaRating, 5 stars1 month 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!!
Top guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 148 reviews

Tuscan farmhouse with private pool and views

MelissaRating, 5 stars1 week 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
Top guest favourite
Villa in Siena
5 out of 5 average rating, 13 reviews

L’Apparita del Peruzzi, pool, super view, save30% 7d +

AlexanderRating, 5 stars1 week ago
An enchanting place. The villa is steeped in history and the gardens with a small amphitheater and a distant view of Siena are spectacular. Great location from which to explore the rest of Tuscany. My family and I have enjoyed our stay.

Villa rentals with a pool

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

Villa Via Francigena

BettyRating, 5 stars1 week ago
Beautiful surroundings, peaceful, beautiful pool! Extremely well-appointed kitchen. Hosts responded immediately if we had any questions.
Top guest favourite
Villa in Colombella
5 out of 5 average rating, 95 reviews

Torre Villa Belvedere Luxury & Relax with pool

MaximilianRating, 5 stars3 weeks ago
We had a fantastic stay! The house was beautifully equipped with everything we needed — from the kitchen to the bedrooms, every detail was thoughtfully arranged. The garden was absolutely lovely, perfect for relaxing in the sun or enjoying a meal outdoors. The pool was a real highlight — clean, spacious, and a great way to cool off during the day. What truly made the stay special was the warm hospitality of our hosts. They were welcoming, helpful, and made us feel completely at home from the very first moment. Highly recommended — we would love to come back!
Guest favourite
Villa in Civitella in Val di Chiana
4.91 out of 5 average rating, 77 reviews

Villa with Pool Casa la Quiete

HannahRating, 5 stars5 days ago
Was a beautiful home to celebrate a 40th with friends and family. Highly recommend
Superhost
Villa in Vicchio
4.89 out of 5 average rating, 53 reviews

Villa in Tuscany with pool, sauna, outdoor jacuzzi

PaulRating, 5 stars2 weeks ago
Cristiana and Mauro were the most friendly hosts. They made us feel immediately comfortable and set us up for a great stay at their wonderful home, offering some fabulous nearby dinner recommendations, as well as directing us to local grocery stores, and train stations for easy day trips into Florence, etc. The farmhouse is beautiful and brimming with character throughout, offering spectacular views over Vicchio. The private swimming pool is bigger than the photos suggest, and not too deep - the kids loved it. The hot tub allows you to sit back and drink in the peaceful Tuscan views. The sauna was a great touch, which we enjoyed throughout our stay, along with the pool table/games room. The outdoor terrace is large and great for a BBQ. The road leading up to the house is a fun drive - we rented a 4x4 (highly recommended if you are planning to stay here) that made it relatively comfortable. We loved our stay and would definitely like to return as there is so much more to explore there!
Top guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 77 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

AmitRating, 5 stars3 days ago
Sometimes you’re lucky to find a great place, and other times a great host—but with this villa, we hit the jackpot and got both. From the moment we booked, Francesco was in touch and incredibly attentive. He went above and beyond to help us celebrate a birthday in our group, organizing flowers, balloons, and a cake for the occasion. He welcomed us in person with a fresh pizza, a fantastic bottle of wine, and garden picked plums. Every morning, he delivered the best pastries we had in Italy and offered excellent recommendations for restaurants and wineries. Villa Tonacato, a charming residence, itself is a private, beautifully maintained property with modern updates, including a well-equipped kitchen, stylish bathrooms, and thoughtful amenities. It’s about a 10–12 minute drive from the charming town of Monte San Savino, which has a lively restaurant scene worth exploring. We had a fantastic stay and are already looking forward to coming back.
Top guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviews

Montemarcoli

TorbjørnRating, 5 stars3 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, 45 reviews

The twigs

JeffreyRating, 5 stars3 weeks ago
Pictures don’t do it justice, prettier in person. Very relaxing get away after spending a few days in Florence.
Superhost
Villa in Greve in Chianti
4.89 out of 5 average rating, 85 reviews

Put down your luggage, this is just the beggining!

CliveRating, 5 stars9 months ago
The villa is situated on the outskirts of Greve in Chianti. For us it was a perfect location - enjoy country views yet walkable to the town centre for restaurants and shops. Four double rooms, each with an ensuite/shower. Everything you need for a great time - swimming pool, terrace with built in BBQ. Kitchen is well equipped with dishwasher, large fridge freezer and large range cooker. Kitchen table was ideal as we could all fit round and it made the kitchen the social hub as we used the comfy lounge for those quieter moments. Definitely recommend. We would be happy to go back.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Casentino
  6. Villa rentals