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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 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.
Superhost
Holiday home in Casole d'Elsa (SI)
4.89 out of 5 average rating, 225 reviews

Studio in Tuscan farmhouse with pool & views

BarbaraRating, 5 stars1 week ago
Fabio and Sarah's farm is a true oasis of peace and tranquility! We were warmly welcomed and immediately felt at home! It was an extremely pleasant stay in the name of nature and the beautiful surrounding landscapes. The pool, overlooking the valley, is really beautiful! The accommodation provided is well maintained and tastefully furnished! Fabio was very helpful and kind: he was a great help in solving a problem we had just arrived! We will definitely return to this paradise... a wonderful place where you slow down and rediscover the beauty of nature 💚 Thanks Fabio and Sarah!
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 stars3 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!
Top Guest favourite
Holiday home in Poggibonsi
4.93 out of 5 average rating, 60 reviews

Il Casale di Villore, Poggibonsi, Siena, Tuscany, Cardisco Apt.

InesRating, 5 stars1 month ago
Perfect! Quiet and beautiful views everywhere. The apartment was so lovely in decor, and so pristine. Lush bedding and towels. Beds were heaven. Shower was amazing. Plenty of activities outside on site. Easy to get to lovely villages by car. I will tell everyone I know how wonderful this estate experience moved my soul. Thank you so much Antonio
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 San Gimignano
4.78 out of 5 average rating, 219 reviews

San Gimignano, Montegonfoli SIX

BillRating, 5 stars1 week ago
Paolo was away so we were left in the quite capable hands of Bruno. Bruno handled checking through checkout (10 days) with ease and humor. Our lodging was as advertised and it was really nice... not luxury but rustic and comfortable and well worth the cost. We highly recommend these lodgings and a big thank you to Bruno!

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.
Guest favourite
Holiday home in Umbertide
5 out of 5 average rating, 16 reviews

Casa Monte

AdamRating, 5 stars10 months ago
Umbria gem. This place was beautiful, clean, comfortable and peaceful. highly recommend it for an Italy getaway we will be back. Gabriele was a kind and welcoming host.
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!
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!
Guest favourite
Holiday home in Bagno A Ripoli
4.91 out of 5 average rating, 33 reviews

Studio apartment in the hills near Florence

JamesRating, 5 stars3 weeks ago
We had a fantastic stay with Violetta! She was warm and welcoming. The place had everything we needed and was clean and comfortable. Was quite close to train stations to link into Florence, but would recommend you have a car. Also, the nearby little town of Villamagna is so charming and worth a day on its own to explore and walk about.
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 gave us 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!
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 stars3 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 stars4 weeks 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 starstoday
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 Pistoia
4.98 out of 5 average rating, 133 reviews

Podere Docciolino Vacation Home

VanessaRating, 5 stars1 month ago
beautiful rustic but modern renovated, furnished with care as if it were an inhabited house. Spotless cleanliness of the rooms and linens, generous and perfectly organized spaces. I wanted to live there all year round! Very kind host and always available. Really great stay. Thank you
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!
Guest favourite
Holiday home in Poggibonsi
4.92 out of 5 average rating, 51 reviews

App.Cavallo - Megognano,2/A

MeridithRating, 5 stars1 week ago
Flaminia’s place was perfect for our few days in Tuscany ! Andrea was quick to respond and help with anything with needed , the place was beautiful and clean , perfect location for the wineries we wanted to visit ! Thank you :)

Destinations to explore

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