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Holiday houses in Chiassaia

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Top-rated holiday rentals in Chiassaia

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Apartment in Centro Storico

4.86 out of 5 average rating, 22 reviews

Tasso Cozy Retreat: 1-BR Airbnb

AshleyRating, 5 stars4 months ago
Masha was such a kind host and very communicative! The airbnb was in a neighborhood that felt safe and it was very walkable into town. The place was clean and we would definitely stay there again!
Guest favourite

Villa in Murlo

5 out of 5 average rating, 11 reviews

Pompana Rustic Charm Casale

VioletaRating, 5 stars4 months ago
Everything was just perfect and even better than it looks in the pictures. Scenic views, beautiful bedrooms, both has it's private bathrooms - kitchen is fully equiped, we didn't miss anything at all! The village is super small, we didn't meet any people during our stay, it seemed that we were alone:) would definitelly recommend it to friends!
Guest favourite

Apartment in Centro Storico

4.98 out of 5 average rating, 122 reviews

Complimentary wine w/ infra-red Sauna

RobertRating, 5 stars1 month ago
I stayed in two different of Donatella’s properties over the course of a week and a half in Florence. I only changed properties because we extended our stay in Florence and the majority of the family members had to leave, we went from 9 to 3 family members. The fact that Donatella was able to accommodate our extended stay in a different property with less people on short notice was wonderful. Both properties were outstanding on every level! They were beautiful, well located, very clean, and well stocked with anything one would require. The property manager, Erika, was a delight and an incredibly responsive. I can't say enough about how positive an experience we had in Donatella's properties. 100% positive feedback. We are already planning our next trip to Florence staying in one of Donatella's properties.
Guest favourite

Home in Prato

4.98 out of 5 average rating, 128 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

JacRating, 5 stars2 months ago
Charming, quiet country setting full of peaceful hikes and relaxation. Ilonka and Rob provide a lovely environment with all necessary amenities, with attention to detail. Arezzo and Assisi are both with an hours drive, Cortana a bit further. We departed our stay fully recharged. Highly recommended for those looking for time away from the pace of today. Deepest gratitude to Ilonka and Rob for their hospitality.
Guest favourite

Apartment in Centro Storico

4.92 out of 5 average rating, 38 reviews

David Suite [Florence Centre, Luxury]

KristenRating, 5 stars2 weeks ago
We loved staying at Sonia’s place!! It was one of our most favorite air bnb’s we have ever stayed in!! It was so nice and had so much character. We loved how fun the decor was but it still felt so elegant. It was clean and we felt right at home. Check in was easy and so was check out! An easy 10 minute walk to the train station and so close to many wonderful restaurants and shops. Would highly recommend, we hope to return again one day!!!
Guest favourite

Holiday home in Porto

4.97 out of 5 average rating, 125 reviews

La Dimora del Lago - Lake views Tuscany and Umbria

OliveraRating, 5 stars1 month ago
We had a fantastic stay! Jan's place is a Tuscan dream – invitingly designed, perfect for feeling good and everything was clean. Even before we arrived, we were greeted by Jan with so much warmth and great tips that we felt right at home from the beginning. Their hospitality and dedication make the stay memorable. Highly recommend! ☺️ Michael & Olivera 🌸
Guest favourite

Apartment in Centro Storico

4.9 out of 5 average rating, 31 reviews

Chic Apartment Macci

JawadRating, 5 stars4 weeks ago
Sergio was very kind and friendly. Apartment is located in nice neighborhood and walkable to many restaurants and public transport. If you are carrying heavy luggage then keep in mind that you have to walk up narrow staircases. Kitchen and bedrooms are spacious. The bathrooms are a bit tight and smaller than I expected but overall we had a good stay.
Guest favourite

Apartment in Peccioli

4.91 out of 5 average rating, 32 reviews

Il Jasmine-Podere Cornacchino

FabioRating, 5 stars3 weeks ago
New accommodation and the listing directions correspond to reality , a very quiet place in the Tuscan hills near the virtuous municipality of Piccioli . Very kind and thoughtful owners to make their customers feel good, you can see the care and passion they have for the property, they stay on the upper floor of the structure .
Guest favourite

Apartment in San Gimignano

4.93 out of 5 average rating, 103 reviews

Apartment "Il Nespolo" - Sunflower Location

LisaRating, 5 stars5 days ago
Stefania's house welcomed us and enveloped us in harmony and silence!!Simple, well-kept and super clean...closing the door behind us was not easy!! Hosts who are available, polite, and respectful. Lisa and Francesco
Guest favourite

Villa in Loro Ciuffenna

4.91 out of 5 average rating, 23 reviews

Villa with pool & view near Florence and Arezzo

WilliamRating, 5 stars4 months ago
I’m a frequent Airbnb guest, in different locations around the world, and I don’t think I’ve had a better experience than here. Simone was spectacularly helpful and friendly , and the meal he made us all on one of our evenings was Michelin star standard. The villa itself was incredibly well equipped, with everything that you could ever wish for, especially in the kitchen which was so well equipped ( and I speak as someone who booked a villa in Sicily in June this year, where the kitchen was quite the opposite) The location was ideal, with a view of the Tuscan hills and the Arno valley to die for. I can’t recommend this villa, and especially Simone, more highly
Superhost

Farm stay in Pienza

4.8 out of 5 average rating, 165 reviews

Holidays in Piandimaggio in Val d 'Orcia.

MarcoRating, 5 stars3 months ago
paolo's beautiful house and in a great location to visit the neighboring countries
Guest favourite

Farm stay in Greve in Chianti

4.87 out of 5 average rating, 188 reviews

The Bartaline Hut

BruceRating, 5 stars3 months ago
We had a lovely stay for 3 nights in Panzano in Chianti. The home was very quiet and peaceful, with beautiful views of surrounding hills and valleys. We stayed at the end of a more urban-focused trip in Italy, and it was wonderful to stay in Panzano and breathe clean air, drink great Chianti, and eat very good food. The hosts were communicative, and helped us with questions, and a good guidebook to the local region was provided. I'd stay there again if I get back to Italy.

Popular amenities for Chiassaia holiday rentals

Other great holiday rentals in Chiassaia

Superhost

Home in Poppi

4.8 out of 5 average rating, 5 reviews

Villa for 22 people w/private pool

Marie-ClaireRating, 5 stars4 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Guest favourite

Apartment in Mercatale Valdarno

4.98 out of 5 average rating, 80 reviews

Panoramic view from stone Apartment- Pool and A/C

ClaireRating, 5 stars4 months ago
While looking for a place to stay it’s often difficult to choose. If we had known how fabulous this place was it would have been a no brainer! We all agreed that this is the best Airbnb we have ever stayed in on all of our travels. Massimiliano was a delight and so personable. He made excellent suggestions one being having a cooking lesson. If you have a chance ask for Francesca! The BEST! One last thing…we left with amazing recommendations for the next part of our trip. Thank you so much for a wonderful stay! Good luck with the harvest!
Guest favourite

Farm stay in Camucia

5 out of 5 average rating, 7 reviews

Il Giardino degli Ulivi | Casa Ippocastano

ViktorijaRating, 5 stars4 months ago
Everything was perfect! Nice place to rest with a wonderful chill lounge and a pool. Federica and Enrica were responsive and helpful hosts. Thanks for the time and all the recomendations.
Superhost

Holiday home in Petriccio

4.57 out of 5 average rating, 7 reviews

Pietra Giglia in Tuscany

TomRating, 5 stars1 month ago
Casita isolated in the middle of Tuscany, 40 minutes from Florence and Siena. 1h from Pisa. In the middle of the Chianti valley. Ideal for visiting both cities and small towns in Tuscany.
Guest favourite

Villa in Asciano

4.95 out of 5 average rating, 75 reviews

Podere on the Crete Senesi

ChulaRating, 5 stars3 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.
Superhost

Villa in Terranuova Bracciolini

5 out of 5 average rating, 3 reviews

Casa al Fiume - Villa with exclusive pool

Patrick Et ElsaRating, 5 stars102 months ago
Ciao, This house and his environment are amazing. It's a real paradise world. A realm of peace and well being. The garden is wonderful, the swimming pool is excellent with the diving and long enough to swim a lot, the river and the forest all around look like a fairy tale. The place is so calm and relaxing. Each morning, when we woke up, we went outside to have our breakfast under nature noises such as birds, trees and waterfall... And what about Barbara and Fulvio? They're so nice and so helpful without being intrusive. They're always available and ready to improve our stay. They are concerned by our confort and they don't hesitate to make us discover typical meals. Thanks to them and we're so happy to meet italian people like them.
Guest favourite

Cottage in Volterra

4.92 out of 5 average rating, 77 reviews

Podere Grignano, beautiful Tuscany.

DanieleRating, 5 stars3 months ago
We had a very nice stay at Roberta and Stephano's place who are friendly and smiling. the cottage is very well equipped especially in the kitchen. you can find everything you need. Sufficient cutlery and dishes. the bedding is comfortable. And the outside of the cottage is very beautiful
Guest favourite

Home in Tavarnelle Val di Pesa

4.94 out of 5 average rating, 125 reviews

La Casa di Nada Home

AustinRating, 5 stars1 week ago
Our stay at this hillside home was nothing short of magical. Tucked away down a private road, the home offers stunning views of Tuscany, and a peaceful atmosphere that we’ll never forget. The house itself is beautifully appointed, with three bedrooms, each with its own attached bathroom, making it perfect for a group or family. The fully stocked kitchen had everything we needed, and the house felt so welcoming. The host was the most gracious and accommodating person we’ve met during our travels. She went above and beyond to make sure we felt at home. The friendly cats roaming around added a nice touch of warmth to the place, too! One of the highlights of our trip was the cooking class hosted by her daughter and her husband. They are not only wonderful cooks but also fantastic company, making the experience truly memorable. It was a real treat to learn traditional Italian dishes while sharing great conversation. This was one of the best experiences we’ve had with Airbnb.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Chiassaia