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Holiday Homes in Casentino

Find and book unique holiday homes on Airbnb

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Popular amenities for Casentino holiday homes

Family-Friendly holiday homes

Guest favourite
Holiday home in Passignano sul Trasimeno
5 out of 5 average rating, 24 reviews

Antico Casale Tiravento - Apartment with balcony

Marcel SarahRating, 5 stars4 days ago
Antonella, Andreas and not to forget Lullu are perfect and so relaxed hosts. They sweetened our mornings with fresh bread, croissants, and coffee. The apartment is well equipped and of high quality. We felt very comfortable right away. The garden invites you to linger and is particularly well maintained. Thank you for this special stay!
Guest favourite
Holiday home in Cortona
4.98 out of 5 average rating, 46 reviews

La Pergola | Farm House with fantastic view

Rasmus RudRating, 5 stars10 months ago
Authentic working home with great views. Lovely location secluded and close to hiking route makes it nice to have a dog with you.
Top Guest favourite
Holiday home in Siena
4.97 out of 5 average rating, 60 reviews

Apartment in historic Villa in Siena_"LE CONTRADE"

PaulRating, 5 stars3 weeks ago
Located a long walk or very short (5 min) drive outside of Siena. Upon arrival, we had a little difficulty locating the apartment parking lot (small entrance off street), but once we knew where it was it was very easy after that. The apartment was wonderful, big for us, and cozy. Cristina was very communicative with us, and recommended many wineries and restaurants in Siena. We really enjoyed our stay and would stay here again.
Guest favourite
Holiday home in Montespertoli
4.95 out of 5 average rating, 136 reviews

Tuscan Orchard

MaryseRating, 5 stars1 month ago
Our host was really warm. and attentive. We had a chance to try their products. She gave us some good recommendations. She was very responsive to our late arrival due to our delayed flight. We would highly recommend this beautiful home and will definitely come back. Thanks for your hospitality. ❤️
Superhost
Holiday home in Asciano
4.87 out of 5 average rating, 101 reviews

Charming home Crete Senesi

TaraRating, 5 stars4 days ago
We had the most wonderful time here, the host was very kind snd helpful, we even met a few of the neighbours, all really friendly and helpful. The views and peacefulness of this house/area made it so special. Waking up to birdsong and roosters everyday. Everything was perfect, thank you.
Top Guest favourite
Holiday home in Lastra a Signa
4.99 out of 5 average rating, 85 reviews

Apartment for 3 agriturismo in Tuscany

Henry & RosalindRating, 5 stars1 week ago
What a beautiful styled property to relax and enjoy the Tuscan scenery in a tranquil setting! We stayed in one of the self contained apartments equipped for cooking. An open dining & kitchen area with a floor-ceiling window allowed us to enjoy the breeze; as all windows have mosquito screens. For morning coffee or sunset glass of wine we could adjourn to an outside table and chairs. The immaculate landscaped garden gently slopes down to an infinity pool inviting you to immerse in the cool water or take shade on a garden lounger under surrounding olive trees as you overlook the wonderful country view. With only few occupants we could enjoy the pool exclusively for a time. Cristina has considered everything and a meticulous eye for design and order is evident all around. The beautiful working kitchen and dining area mimic those in interiors magazines and a culinary prowess is apparent if you choose to enjoy Cristina's luxuriant breakfast, which we implore you to experience at least once!
Guest favourite
Holiday home in Borgo San Lorenzo
4.98 out of 5 average rating, 80 reviews

Villa Porcigliano Olive Grove

FrancescoRating, 5 stars5 months ago
Really nice location in a peaceful environment. Jacopo has been really responsive from the booking until the check-out, giving us also useful advice.
Guest favourite
Holiday home in Florence
4.9 out of 5 average rating, 710 reviews

charming studio ponte vecchio/ lift

ZijunRating, 5 stars2 weeks ago
It was a fantastic stay ! The apartment is cozy and clean with great recommendations of the best restaurants and places to eat and drink. Maria Paola is super friendly and welcoming. Communications with her is super fluid. The location is perfect with walking distance to the touristy spots! Super great stay highly recommend !

Holiday home rentals with a patio

Guest favourite
Holiday home in Greve in Chianti
4.96 out of 5 average rating, 72 reviews

Sangiovese house with mini-pool in the center of Greve

JustinRating, 5 stars1 week ago
Alessandro is a fantastic host. The apartment is exactly as described and was perfect for a week long stay with four adults. The restaurant downstairs, the convenient bus stop, the convenient parking, all made this such a unique and perfect place to enjoy the region. This is simply the perfect balance of what our adult family of four was looking for. We are already trying to make plans to return and we would change our dates to make sure we can stay here again.
Guest favourite
Holiday home in Monteroni d'Arbia
4.9 out of 5 average rating, 73 reviews

White lily with a view of Siena

JoanRating, 5 stars1 week ago
we all loved White Lily. it was serene with a beautiful setting in the countryside. we would return if we were n the area again.
Top Guest favourite
Holiday home in Umbertide
5 out of 5 average rating, 16 reviews

Casa Torre

JoannaRating, 5 stars8 months ago
We had a magical stay at this house! He surroundings are breathtaking and lots of space for my kids to run around and explore the natural beauty. We felt right at home in this house and it was the perfect base for us to go out exploring everyday. We can only hope to return on our future travels.
Superhost
Holiday home in Ulignano
4.72 out of 5 average rating, 18 reviews

★ Relaxing apartment & stunning view of Tuscany ★

Anna-LenaRating, 5 stars10 months ago
We went there for the second time and it was just perfect as the first time. Diego's property is beautiful overlooking San Gimignano, it is quiet and very idyllic so you can really unwind. The apartment was great, is well equipped with everything you need. We felt very comfortable and would love to come a third time next year. Thanks to Giorgia for the good communication and flexible check-in.
Guest favourite
Holiday home in Certaldo
4.93 out of 5 average rating, 15 reviews

La Selva , Country house, 130 mq, Stunning views

LindaRating, 5 stars1 month ago
Staying with Carmine is top. We have been to Carmine and Alessandra in Certaldo for a month (mid-April / mid-May) and we can recommend that to everyone. Not only the reception ( in our case very late) was incredibly warm, but throughout our stay we felt very comfortable, this host is always open to questions, is proactive with giving information, tips about everything like where it is nice / tasty/ beautiful to visit. In addition, the house is very nice, it is great in the Tuscan hill country, between the wine and olive farmers, nice beds (we always find important especially if you are staying there longer) and really good Wi-Fi which was important for us to be able to work from here. The location is perfect. You are close to Florence, Siena, Pisa, and many special other villages/towns that are more than worth visiting. The month was over too soon! If we visit Tuscany again for sure with Carmine and Alessandra!
Superhost
Holiday home in Impruneta
4.84 out of 5 average rating, 51 reviews

Home La Mimosa: between Firenze and Chiantii

Cinthia MarjoryRating, 5 stars6 days ago
A place where nature is noticed, and the kindness of Roberta and her son have been key to having a beautiful and comfortable place to stay. We appreciate your service, we look forward to returning soon.
Guest favourite
Holiday home in Gaiole in Chianti
4.96 out of 5 average rating, 28 reviews

The Piccola Villa of Borgo Argenina

MeghanRating, 5 stars3 weeks ago
This was our favorite place we stayed in Italy and we went to three other locations. The view is unbeatable and so much to do nearby. We went to a few wineries and ate at Malborghetto (Highly recommend for an authentic experience and small town feel!). We hope to come back! Communication with hosts was great. amenities such as the pool, breakfast, the kitchen, were awesome. Thanks so much for a wonderful stay!
Top Guest favourite
Holiday home in Pieve Vecchia
5 out of 5 average rating, 36 reviews

Il Casale di Lucullo, your home in Tuscany!

AngelikaRating, 5 stars2 weeks ago
The little cottage was very nice and cozy. There was everything you need. The reception was personal, very nice and friendly. Michaela showed us everything and made many recommendations. Even when we had questions, she answered very quickly. The whole family is very nice and friendly. We felt very comfortable. Thank you!

Holiday home rentals with a washing machine and dryer

Top Guest favourite
Holiday home in Casole d'Elsa - Siena
4.97 out of 5 average rating, 30 reviews

Elegant farmhouse surrounded by nature, Terra

EdytaRating, 5 stars1 month ago
We stayed ar Romina's and Riccardo with a couple of friends. We enjoyed our lovely apartment and beautiful peaceful property surrounded by olive trees and herbs. Our hosts were super friendly and helpful, especially since airline lost one of our friends' luggage. Romina helped us communicate with DHL and went above and beyond to make sure it was delivered. Riccardo gladly explained the kind of plants they were growing and harvesting for essential oils. We enjoyed the company of Luna the cat who came visit but was politely staying outside. Wildlife is abundant and nature unspoiled - truly a magical place! The area is quite remote so it may not be convenient to everyone. The closest little town is Casole d'Elsa where you can find 2-3 restaurants and a pharmacy, larger supermarkets are within 20min drive. It's a great starting point to visit Siena, San Gimignano, Volterra. The apartment is well equipped with small stove, dishwasher, fridge and microwave. Highly recommend!
Superhost
Holiday home in Laterina
4.73 out of 5 average rating, 11 reviews

Apartment with pool and restaurant

StefaniaRating, 5 stars1 month ago
the stay was perfect. The attention to detail distinguishes it. The possibility of bringing the puppy was super appreciated. The restaurant deserves a great applause. I highly recommend it.
Top Guest favourite
Holiday home in Figline e Incisa Valdarno
5 out of 5 average rating, 42 reviews

Farmhouse in the countryside with swimming pool Solatìo

ZachRating, 5 stars1 month ago
We highly recommend Marco's Airbnb! The apartment itself is stylish and spotlessly clean, with exceptionally comfortable beds ensuring a restful night's sleep. What truly stood out was Marco's outstanding hospitality. His local recommendations were spot on, and when we had a slight navigation mishap, he went above and beyond by personally guiding us to the property. Marco's responsiveness and care made our stay truly memorable. Thank you!
Guest favourite
Holiday home in Florence
4.91 out of 5 average rating, 274 reviews

Melarancio Residence

PeggyRating, 5 stars4 weeks ago
We stayed here for 4 nights. 3 of us had enough space and the place was exactly as described. The location could not be better than this. Lots of great restaurants around it and all the main tourist sites are walking distance. Also walking distance from the train station (we came to Florence via train from another location and we walked to this place. It was short distance so we were able to walk with very large luggage). We were so relieved that the building has an elevator. Check in process was easy and flexible. I highly recommend this place.
Guest favourite
Holiday home in Fiesole
4.87 out of 5 average rating, 52 reviews

[Colline Firenze] Borgo Le Palaie

DannyRating, 5 stars1 month ago
Beautiful Home! Highly recommend for anyone visiting the Tuscany region
Top Guest favourite
Holiday home in Florence
5 out of 5 average rating, 53 reviews

GREEN like hope in Florence

AmyRating, 5 stars1 day ago
The most wonderful Airbnb we have ever stayed in! Claudia was delightful! The apartment is beautiful and so thoughtfully designed. It is a work of art! The location is perfect - close to everything!
Top Guest favourite
Holiday home in Florence
4.98 out of 5 average rating, 47 reviews

Appartamento Donizetti24 (D24)

WesleyRating, 5 stars1 week ago
One of the best Airbnb’s I’ve stayed at during this trip. Sara was very helpful and responsive. It was very peaceful. The bus station is right around the corner and easy to get anywhere. Very pleased!
Guest favourite
Holiday home in Florence
4.92 out of 5 average rating, 165 reviews

TOSCANELLA QUARTZ STUDIO

PedramRating, 5 stars2 weeks ago
Great host, great communication, friendly! Great spot close to attractions and amazing restaurants! We will definitely come back!

Destinations to explore

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