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Villa holiday rentals in Casentino

Find and book unique villas on Airbnb

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Popular amenities for Casentino villa rentals

Private villa rentals

Guest favourite
Villa in Castiglion Fiorentino
4.98 out of 5 average rating, 65 reviews

Tuscany Villa Mammi

ClarissaRating, 5 stars1 week ago
There were 10 of us staying in Simone’s villa and it was such a lovely place to relax. The outside area was huge with many different seating areas. The pool looking over the town below was stunning. Simone was really responsive to any questions we had and gave us suggestions for wine tours and taxis. The indoor kitchen is a little small but still has everything you need. We used the outdoor bbq and pizza oven much more as this was perfect for cooking outside in the sunshine. Thank you for a great stay!
Top Guest favourite
Villa in Anghiari (Arezzo)
4.99 out of 5 average rating, 94 reviews

In a sunny, quiet and rustic area.

JolandeRating, 5 stars2 weeks ago
Ik kan mij volledig aansluiten bij alle positieve reviews, de ontvangst was aller hartelijkst de koelkast was gevuld de wijn en de chocolade taart stond op tafel. we werden regelmatig verrast met heerlijkheden waaronder kersen uit eigen boomgaard . Kortom aan het onderkomen ontbrak niks. Ook de aanwijzingen voor parkeren in Arezzo, fietstochten etc waren geweldig. Heb nog nooit zulke fijne verhuurder mee gemaakt. Hartelijk dank voor alles Jolande en Gert Jan
Top Guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Sestuccina

RubyRating, 5 starstoday
Wunderschöne Unterkunft! • super schön gelegen (sehr viel Natur und sehr ruhig) • Kommunikations immer reibungslos • tolle Restaurants und leckeres Eis innerhalb 5 Minuten Fahrtzeit • Ausstattung genau wie angegeben würde ich immer wieder weiterempfehlen! Luciano und Brigitta sind super Gastgeber 😊
Guest favourite
Villa in Asciano
4.93 out of 5 average rating, 88 reviews

Casa Bianca gorgeous Tuscan home, Crete Senesi

Johannes KarlRating, 5 stars1 week ago
Entspannend, angenehmer Aufenthalt mit toller Aussicht, schön angelegtem Garten und nicht zu weit von Siena entfernt
Superhost
Villa in Campogialli
4.68 out of 5 average rating, 25 reviews

VILLA DI CHARME NEL CHIANTI

LlucRating, 5 stars1 month ago
Cuando piensas en un siitio tranquilo, bonito, donde descansar y con todas las comodidades… este sitio encaja perfectamente!! Desayunos buenísimos y todo hecho en casa!! Por último, destacar su amabilidad y saber hacer… un 10!!
Superhost
Villa in Terranuova Bracciolini
4.86 out of 5 average rating, 7 reviews

Casa al Fiume - Villa with exclusive pool

JaninaRating, 5 stars1 week ago
Wir hatten eine unvergessliche Woche in diesem liebevoll eingerichteten Haus mitten im toskanischen Tal. Alles war super sauber, die Lage traumhaft – absolute Ruhe und Natur pur. Barbara und Fulvio sind echte Herzensmenschen: herzlich, aufmerksam, einfach wunderbar! Unsere 3-jährige Tochter hat sich genauso wohlgefühlt wie wir. Wir können diesen Ort aus tiefstem Herzen empfehlen – volle Punktzahl!
Guest favourite
Villa in Poppi
5 out of 5 average rating, 27 reviews

Country house with private pool (2 villas, 10 pax)

HelenRating, 5 stars3 weeks ago
The two apartments and the pool are brilliant, perfect for two families with children. The pool especially is clean and large - a little cold in May but that didn't stop the kids being in all day! The kitchens are well equipped and the dining table outside is lovely for eating, games and hanging out. Elena was an amazing host being very helpful and making us a restaurant reservation at a great place nearby with an amazing view. Good base to visit Poppi, the castle is worth seeing. The only thing to mention - don't bring an SUV as it is a tight fit down the drive! And there are no walkable restaurants, but we knew that beforehand and the local supermarket has everything you could want. There is also a takeaway pizza place ten minutes drive away. we had a wonderful time and would love to come back.
Superhost
Villa in Pierle
4.9 out of 5 average rating, 30 reviews

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

HaisamRating, 5 stars1 week 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

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 Montecucco
4.91 out of 5 average rating, 43 reviews

Villa Angiolina

PamelaRating, 5 stars1 week ago
Laura was an amazing host and made sure we knew all the details of the house and was very responsive if we had a question. The house itself is gorgeous and so are the surroundings. Highly recommend staying here as a home base in the Tuscany area! We visited many surrounding cities as well as a winery 40 minutes south. We would also recommend the restaurant Nuevo Ranch right done the street! Wonderful!
Superhost
Villa in Greve in Chianti
4.84 out of 5 average rating, 32 reviews

Romantic Villa with private pool and fabulous view

ReubenRating, 5 stars1 week ago
Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!
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!
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

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!!
Guest favourite
Villa in Tignano
4.95 out of 5 average rating, 171 reviews

Villa Isabella

DouglasRating, 5 stars4 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 stars5 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
Top Guest favourite
Villa in Cortona
5 out of 5 average rating, 11 reviews

Villa Leopoldina, 6 pax, Private Pool

MaximeRating, 5 stars9 months ago
Gigi’s place is one of the most peaceful places we’ve stayed in in Italy. The location is gorgeous and perfectly located between different towns to explore (Cortona, Arezzo, Montepulciano to name a few). A car is necessary but you can get to the town center for groceries and local produce in 10 minutes. We enjoyed spending our days by the pool, cooking and barbecuing in the garden. The kitchen was the most equipped I’ve ever seen for an Airbnb and the house was spotless. Extra supplies were left for us as well if we needed which was a nice touch. Gigi was always available for recommendations and extremely friendly. If you’re looking for calm and quiet this is your place!!

Villa rentals with a pool

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 stars2 months ago
Bereits im Vorfeld wurden wir von Emanuele kontaktiert. Er hat uns die Wegbeschreibung geschickt, damit wir das Haus problemlos finden können. Wir wurden sehr herzlich mit regionalen Spezialitäten und Wein empfangen. Der Aufenthalt war super, wir haben uns sehr wohl gefühlt. Während des Aufenthalts haben wir ganz viele Tips bezüglich Essen und Ausflugsmöglichkeiten von Emanuele erhalten. Er war sehr hilfsbereit und immer erreichbar. Wir werden bestimmt wiederkommen.
Top Guest favourite
Villa in La Cima
4.94 out of 5 average rating, 32 reviews

- 20% Last Minute 21June-2July Lake View Villa

BenRating, 5 stars2 weeks ago
Wir hatten einen tollen Aufenthalt bei Sheetal und Vittoria. Die Unterkunft sowie der Garten/Pool waren wunderschön, wie beschrieben und alles ist sehr ordentlich und sauber. Die Küche war sehr gut ausgestattet und hatte alles, was man benötigt. Die Unterkunft liegt etwas erhöht in einem kleinen Dorf oberhalb von Touro, was einen wunderschönen Blick auf den See ermöglichte. Wir würden definitiv wieder kommen!
Guest favourite
Villa in Civitella in Val di Chiana
4.91 out of 5 average rating, 76 reviews

Villa with Pool Casa la Quiete

Harald SkagestadRating, 5 stars2 weeks ago
Better than expected! We loved staying at Milenas house in beautifull Toscana.
Guest favourite
Villa in Passignano sul Trasimeno
4.9 out of 5 average rating, 31 reviews

Villa con piscina panoramica • Lago Trasimeno

MelanieRating, 5 stars1 week ago
An amazing hideaway in the hills! Takes you into holiday mode & switching off in the beautiful setting surrounded by nature & incredible views. So glad we booked & would love to go back again. Paulo, and family, were so helpful, kind & responsive. The area whilst quiet is very welcoming to tourists & we met many friendly people who would always help us out on our way. The house itself is stunning & huge. The bathrooms are dated but they work fine & everything functions as it should so it really isn’t a problem so don’t be put off by that. The linens are incredible & the beds very comfortable. Air conditioning works well. Kitchen well equipped & house has an abundance of space and beautiful furniture to relax in, inside and out. Honestly the scenery outside was incredible & we spent every minute we could outside which is a shame only because the house was also beautiful. The pool was fabulous & it was hot enough that heating wasn’t needed.Didn’t use sauna or spa,needed longer! Miss it!
Top Guest favourite
Villa in Marciano della Chiana
4.95 out of 5 average rating, 78 reviews

La Bacaia

JorgeRating, 5 stars1 week ago
We thoroughly enjoyed our stay. The house is conveniently located in the heart of the Valdichiana with easy and clear access to the surrounding towns. The grounds were beautifully landscaped with a combination of olive trees, grapevines, flowers and even herbs like rosemary, basil and mint that we used in our cooking. The rooms were spacious and very private. Our group of 6 were more than comfortably accommodated, each with its own bathroom and AC units that worked well. The two kitchens served us well. We mainly utilized the outside kitchen as the weather throughout our stay was perfect. The kitchens were well stocked with all of the necessary cooking items. There were some items that we needed to purchase at the local supermarket, including shower gel, paper towels, napkins, etc. For a one week stay we would recommend extra towels, especially for the pool. Overall, I would highly recommend La Bacaia as a base to fully enjoy your Tuscan vacation.
Top Guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 75 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

DavidRating, 5 stars1 week ago
We had an amazing time in Francesco's place. The house is wondefull. Spacious, clean and very modern. The garden and surroundings are very beautiful. Francesco is an excellent host. He is responsive and his service is ourstanding. He welcomed us with pizza and wine en he even brought us a box with delicious treats for breakfast every morning. I can recommend Francesco's place for everyone who want to stay in a central location to discover Tuscany and stay in a charming house full of luxury. Couldn't be better.
Guest favourite
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.
Guest favourite
Villa in Scrofiano
4.86 out of 5 average rating, 94 reviews

SacroFanum Villa

ClaudiaRating, 5 stars2 days ago
Wir hatten eine wundervolle Zeit in der Villa! Die Aussicht auf die toskanische Landschaft und auf Scrofiano ist einfach atemberaubend . Der Pool war ein echtes Highlight: gepflegt, ruhig gelegen und perfekt, um die Seele baumeln zu lassen. Manola und Martha waren sehr freundlich und hilfsbereit, standen bei Fragen jederzeit zur Verfügung. Insgesamt eine rundum entspannte Zeit – wir kommen bestimmt wieder!

Destinations to explore

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