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House holiday rentals in Casentino

Find and book unique houses on Airbnb

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Popular amenities for Casentino house rentals

House rentals with a pool

Top Guest favourite
Home in Poppi
5 out of 5 average rating, 51 reviews

Villa Podere Cerretino

Emma KamperRating, 5 stars2 weeks ago
Fabulous place in amazing surroundings. The pool area is wonderful and the garden beautiful. We had an amazing time and enjoyed the entire place - especially the outdoor pizza oven. Nicola was very helpful and fast in his responses.
Guest favourite
Home in Arezzo
4.9 out of 5 average rating, 166 reviews

Italian Interior

LloydRating, 5 stars8 months ago
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!
Superhost
Home in Pievescola
4.93 out of 5 average rating, 106 reviews

Antico Borgo Ripostena – n. 9 Oil Mill

DanielRating, 5 stars2 weeks ago
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 263 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Top Guest favourite
Home in Bagno A Ripoli
4.95 out of 5 average rating, 139 reviews

Casetta Melograno – Cozy farmhouse in Chianti

JacobRating, 5 stars1 day ago
I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 107 reviews

The Owl: view, pool and garden

StephenRating, 5 stars1 month ago
We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Superhost
Home in Florence
4.83 out of 5 average rating, 113 reviews

Country House w/ heated Pool near the City Centre

SandraRating, 5 stars2 months ago
We thoroughly enjoyed our stay at this wonderful place. The quiet surroundings were perfect for a break from the hustle and bustle of Florence. And it's still easily accessible by tram. Giacomo was a wonderful host and was always available. We truly enjoyed every day there.

Weekly house rentals

Top Guest favourite
Home in Castel Focognano
5 out of 5 average rating, 20 reviews

Tuscan Rustic

GrahamRating, 5 stars7 months ago
We loved our stay, the villa is beautifully done, has all of the amenities needed, was spotlessly clean and our hosts were so welcoming and provided lots of recommendations on places to visit and even made us a delicious pizza and shared a local wine. The view from the villa is breathtaking, watching the clouds roll through in the distance every morning whilst eating breakfast was amazing. Highly recommend.
Top Guest favourite
Home in Poppi
4.97 out of 5 average rating, 29 reviews

historical townhome in Poppi

JacobRating, 5 stars2 weeks ago
This is hands-down the best AirBnB in the best little town in Italy. It’s the first time I’ve ever driven into a literal castle to park my car. Hopefully it won’t be my last. Joana was incredibly kind, responsive, and helpful. And she gave very clear instructions for arriving at and entering her apartment—not an easy feat in Italy. My favorite part of my stay was opening my windows in the morning and being greeted by an adorable nonna in the apartment across the street—“Buongiorno!” If you’re looking for a bona fide, non-touristy Italy experience, this is the spot for you.
Guest favourite
Home in Bibbiena
4.96 out of 5 average rating, 47 reviews

Charming house of the past next to the stream.

NickRating, 5 stars4 days ago
Casa Lisa is a rustic, authentic sanctuary away from the hustle of today’s mayhem yet all the everyday amenities are a short driveway. We had a wonderful few days here our hosts went out of their way to ensure we had a lovely time, hopefully we will return in the future.
Top Guest favourite
Home in Pontassieve
4.96 out of 5 average rating, 82 reviews

The charming cottage in Tuscany with breathtaking views

SamiRating, 5 stars5 days ago
So Beautyful location and views. House is charming and clean. we recommend.
Guest favourite
Home in Quota
4.92 out of 5 average rating, 24 reviews

Casa Marta - Quota's houses

NicoleRating, 5 stars1 week ago
Our Italian tour could not have started better than in Claudia's cozy cottage, with her warm nature and the beautiful view of a wonderful landscape. We felt very comfortable and can only recommend this accommodation! It had everything you needed. The village immediately slows down and both the small village shop with bar and the altitude ensure peace and relaxation.
Top Guest favourite
Home in Chiaveretto
4.98 out of 5 average rating, 45 reviews

Oleandro, cozy studio in Val di Nima

CarolynRating, 5 stars1 week ago
Nicola bnb was amazing! Perfect to relax and such a lovely bnb. Nicola is the perfect host. Highly recommend. So very beautiful with surrounding huge mountains. A great base to explore surrounding areas. And a bonus, the cats are geougous. Thank you
Guest favourite
Home in Pelago
4.92 out of 5 average rating, 65 reviews

Chianti House Garden - 30m Florence center- A/C

DagmarRating, 5 stars3 weeks ago
Nice and spacious place to stay. Plenty of space and quietly located in the middle of a residential complex. Car is necessary. From Pontessieve, Florence is then easily reachable by train. Pamela has made many suggestions for activities and was quick to respond to questions and requests. It was a successful stay for us🍀
Top Guest favourite
Home in Chiusi della Verna
4.99 out of 5 average rating, 77 reviews

Casa Carla

DaniloRating, 5 stars1 week ago
The experience in Carla's villa is by far the best I've ever had with Airbnb. The house is close to other villas but with a large well-kept garden of roses and medicinal plants and with deck chairs in which to spend moments of absolute calm. Carla waited for us in person to offer us a very welcome tart and explain every detail of the apartment, equipped with TV, wifi and all the kitchen equipment (very, very nice), including a kettle, coffee machine and pods and a nice and welcoming decor. The bed is the best on Airbnb. Absolute peace. The only regret: we only stayed two nights.

Private house rentals

Top Guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars4 weeks ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Superhost
Home in Barberino Tavarnelle
4.76 out of 5 average rating, 55 reviews

7 min Cantina Antinori | Pool | Casa Sala & Pepe

RyanRating, 5 stars1 month ago
Beautiful home near Chianti. Clean and comfortable, with amazing vineyard/sunset views. The hosts were very responsive and friendly, and they gave clear instructions. One thing to note is that the property is listed as "Entire Home", but it is actually a condominium that shares walls and outdoor common areas with the neighbors. There is a divider in the backyard between us and the neighbors, but it is not completely private. Overall, we had a great time here.
Guest favourite
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars1 week ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Guest favourite
Home in Arezzo
4.88 out of 5 average rating, 24 reviews

Colonial house immersed in a natural park.

MarieRating, 5 stars10 months ago
We spent two weeks at Rolando and Patrizia's with our two one-year-old and three-year-old children. The place is absolutely beautiful with a sublime view. They had a lot of little touches for our children throughout the stay. It was always a pleasure to chat with them. Accommodating, very considerate. The kids were always happy to see them. As for the house, it is very nice and easy to live in. The two terraces are a real plus. And again the views filled us throughout our stay.
Superhost
Home in Reggello
4.8 out of 5 average rating, 82 reviews

House with pool among olive trees plantation

KarolinaRating, 5 stars8 months ago
The apartment is located in the picturesque surroundings. It takes quite a while to get there up the hill, but the views reward it! The place was clean and well-prepared for our stay. Good spot if you look for some peace and quiet and want to stay away from the noise!
Superhost
Home in Frassineta
4.78 out of 5 average rating, 9 reviews

La Fonte Casentino Guest House

LamineRating, 5 stars2 months ago
We had a great time in the middle of nature, tranquility, clean air and with a great view. Eleonora was always kind and helpful, very warm welcome.
Top Guest favourite
Home in Castelfranco Piandiscò
4.96 out of 5 average rating, 82 reviews

Villa close to Florence amazing view private pool

Ane ElineRating, 5 stars8 months ago
Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!
Superhost
Home in Londa
4.96 out of 5 average rating, 25 reviews

Luxury Country Retreat near Florence with Jacuzzi

BenediktRating, 5 stars1 month ago
We really enjoyed our stay there. Beautiful house and outside areas with great view. The hosts were really nice and welcomed us perfectly, we also received really good recommendations for local restaurants. I can definitely recommend staying there.

Destinations to explore

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