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House holiday rentals in Casentino

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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!
Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars2 days ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
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 San Miniato
4.92 out of 5 average rating, 133 reviews

Private villa/swimming pool in Tuscany

MārcisRating, 5 stars1 week ago
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 263 reviews

Charming estate with views

AndrewRating, 5 stars5 days 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, 138 reviews

Casetta Melograno – Cozy farmhouse in Chianti

JennaRating, 5 stars1 week ago
Sonia was extremely helpful from start to beginning. Gave us great recommendations which ended up being some of our favourite nights! The most stunning location and beautifully kept place, with everything you could possibly need to live in. 30 mins from Florence, 1 hour from Siena and miles of beautiful scenery and wineries as far as the eye can see As a british couple in our 20’s we loved our stay here ❤️
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

Weekly house rentals

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.
Top Guest favourite
Home in Bagno A Ripoli
4.99 out of 5 average rating, 161 reviews

Tuscany .Countryhouse on the Florence's hills

MaximilianRating, 5 stars2 weeks ago
It wasn't a holiday home - it was a home for us. Rarely have I felt so incredibly comfortable - the garden is a dream, the house is very cozy and there are well thought-out details everywhere. You can enjoy wonderful privacy in your own garden with your own entrance, but if you need something, Flora and Luca have always been there for us and we immediately took them to our hearts!!! Florence is of course also enchanting and you can go on great excursions! We will miss all of this very much and hopefully come back soon!
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 stars2 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 stars3 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, 44 reviews

Oleandro, cozy studio in Val di Nima

CarolynRating, 5 stars6 days 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
4.94 out of 5 average rating, 64 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 San Gimignano
4.99 out of 5 average rating, 189 reviews

Garden House

MargaretRating, 5 stars1 week ago
My husband and I spent a wonderful week staying in Mario’s beautiful Casa del Giardino. Everything about the house and its beautiful garden, complete with resident tortoise Mr T, is perfect. Full of charm, it’s a real oasis right in the heart of San Gimignano. The house is very well equipped and Cristina was a wonderful hostess who responded very quickly to any questions we had. The welcoming wine was a much appreciated treat. I would definitely recommend this as an ideal place to stay in San Gimignano.

Private house rentals

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

Hidden gem in Tuscany

MitchellRating, 5 stars3 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.
Guest favourite
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars2 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
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!
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!
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.
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.
Top Guest favourite
Home in Arezzo
5 out of 5 average rating, 12 reviews

Villa Medici Donnini Superior Apartment

RobertRating, 5 stars3 weeks ago
We had a wonderful week-long visit. I wish we had stayed longer. The villa is beautiful. It is spacious, clean, with modern amenities and appliances but also has some very nice antique furniture and decor. The outdoor patio is really amazing, with views of distant Tuscan hills and farms, olive and cypress trees - a great place to eat and relax outdoors. Nearby Arezzo is a great place to visit. There are many interested museums, churches and places to visit in the older section of the town (including the Basilica di San Francesco with frescoes by Piero della Francesca), but there are also more modern parts of town with shops and restaurants, and ample parking. The villa is also within easy driving distance of many other surrounding towns (such as Cortona) and places to visit. Our hosts were super helpful and friendly, and we especially enjoyed the olive oil that is provided and made from the trees growing on the property. We would definitely stay here again.
Superhost
Home in Lucignano
4.95 out of 5 average rating, 38 reviews

La Casetta

LauraRating, 5 stars1 month ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!

Destinations to explore

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