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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
Autentisk fungerende bolig med fantastisk udsigt. Dejlig placering ugeneret og tæt på vandrerute gør det dejligt at have hund med.
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
Il podere di Fabio e Sarah è una vera oasi di pace e tranquillità! Siamo stati accolti amichevolmente e fin da subito ci siamo sentiti a casa! È stato un soggiorno estremamente piacevole all’insegna della natura e degli splendidi paesaggi circostanti. La piscina, con veduta sulla valle, è davvero splendida! L’alloggio messo a disposizione è ben curato e arredato con gusto! Fabio è stato molto disponibile e gentile: ci è stato di grande aiuto per risolvere un inconveniente che abbiamo avuto appena arrivati! Torneremo sicuramente in questo paradiso..un luogo stupendo dove si rallenta e ci si riappropria della bellezza della natura 💚 Grazie Fabio e Sarah!
Guest favourite
Holiday home in Montespertoli
4.95 out of 5 average rating, 136 reviews

Tuscan Orchard

MaryseRating, 5 stars1 month ago
Notre hôte était vraiment chaleureuse. et à l'écoute. Nous avons eu l'occasion de goûter à leurs produits. Elle nous a donné de bonnes recommandations. Elle a été très réceptive suite à notre arrivée tardive dùe à notre vol retardé. Nous recommandons fortement cette belle maison et y reviendrons assurément. Merci pour votre accueil ❤️
Superhost
Holiday home in Asciano
4.87 out of 5 average rating, 101 reviews

Dimora di fascino 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

Casa Sangiovese con mini-piscina in centro a 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 con vista su Siena

LouisaRating, 5 stars2 days ago
Wir hatten tolle Tage bei Marta und haben uns sehr wohl gefühlt. Die Unterkunft ist etwas außerhalb und man ist auf das Auto angewiesen. Die Unterkunft ist sehr hübsch und man hat alles was man braucht. Wir würden wieder kommen :)
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
Wir waren schon zum zweiten Mal dort und es war wie auch schon beim ersten Mal einfach nur perfekt. Diegos Anwesen ist wunderschön mit Blick auf San Gimignano, es ist ruhig und sehr idyllisch sodass man richtig gut abschalten kann. Das Apartment war super, ist gut ausgestattet mit allem was man braucht. Wir haben uns sehr wohl gefühlt und würden uns freuen nächstes Jahr ein drittes Mal zu kommen. Danke an Giorgia für die gute Kommunikation und den flexiblen 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
Verblijven bij Carmine is top. Wij zijn een maand (half april / half mei) bij Carmine en Alessandra in Certaldo geweest en dat kunnen we iedereen aanraden. Niet alleen de ontvangst ( in ons geval heel laat) was ontzettend hartelijk maar gedurende ons hele verblijf hebben we ons heel comfortabel gevoeld, deze host staat altijd open voor vragen, is pro actief met geven van informatie, tips over van alles zoals waar het leuk / lekker/ mooi is om te bezoeken. Daarnaast is het huis hartstikke fijn, het ligt geweldig in het Toscaanse heuvelland, tussen de wijn en olijf boeren, fijne bedden (vinden wij altijd belangrijk vooral als je er langer verblijft) en echt goede wifi wat voor ons belangrijk was om zo ook van hieruit te kunnen werken. De locatie is perfect. Je zit dichtbij Florence, Siena, Pisa, en vele bijzondere andere dorp/stadjes die het bezoeken meer dan waard zijn. De maand was te snel voorbij! Als we nog eens Toscane bezoeken zeker weten bij Carmine en 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

Monolocale in collina a due passi da Firenze

MoritzRating, 5 stars2 weeks ago
Wir waren für einige Tage Gäste bei Violetta und können die Unterkunft sehr empfehlen! Vor allem durch die freundliche und herzliche Art und Weise von Violetta haben wir uns von der ersten Minute an sehr wohl gefühlt und konnten unseren Urlaub sehr genießen. Sie spricht akzentfrei Deutsch und hat sich immer Zeit für uns genommen und uns beim Planen für unsere Stadtbesichtigung in Florenz oder auch Restaurants mit Insider-Tipps unterstützt. Ankunft, Abreise und auch alles vor Ort war sehr flexibel und unkompliziert. Wer neben Tagesausflügen (zentraler Parkplatz in Florenz ist in ca. 30 min zu erreichen) vor allem die Ruhe und Natur genießen will, ist hier genau richtig! Die Aussicht über die Hänge und der entfernte Blick auf Florenz sind toll und wir können die Unterkunft für Toskanaurlauber nur wärmstens empfehlen. Ohne Auto ist die Unterkunft jedoch nicht zu empfehlen, da man nur über eine enge Straße zur Unterkunft gelangen kann und hier mit dem Auto schon knapp 15 min braucht.
Top Guest favourite
Holiday home in Pieve Vecchia
5 out of 5 average rating, 36 reviews

Il Casale di Lucullo, la tua casa in Toscana!

AngelikaRating, 5 stars2 weeks ago
Das kleine Häuschen war sehr schön und gemütlich. Es gab alles was man braucht. Der Empfang war persönlich , sehr nett und freundlich. Michaela hat uns alles gezeigt und uns viele Empfehlungen gemacht. Auch wenn wir Fragen hatten, hatte sie sehr schnell geantwortet. Die ganze Familie ist sehr nett und freundlich. Wir haben uns sehr wohl gefühlt. Vielen Dank!

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

Elegante agriturismo immerso nella natura, 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

Casa colonica nel verde con piscina 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

JuliaRating, 5 stars1 week ago
Der Aufenthalt war sehr schön. Die Wohnung war perfekt und schön und ruhig gelegen. Wir kommen gerne wieder!
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 casa vacanze

VanessaRating, 5 stars1 month ago
bellissimo rustico ma ristrutturato moderno, arredato con cura come se fosse una casa abitata. Pulizia degli ambienti e della biancheria impeccabile, spazi generosi e organizzati alla perfezione. Mi è venuto il desiderio di viverci tutto l'anno! Host gentilissima e sempre a disposizione. Davvero un ottimo soggiorno. Grazie
Guest favourite
Holiday home in Florence
4.92 out of 5 average rating, 165 reviews

TOSCANELLA STUDIO QUARZO

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

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  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Casentino
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