
Holiday rentals in Castiglion Fiorentino
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Top-rated holiday rentals in Castiglion Fiorentino
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Castiglion Fiorentino
Guest favourite

Cottage in Castiglion Fiorentino
4.96 out of 5 average rating, 28 reviewsCharming Cottage with Pool
YaoRating, 5 stars4 weeks ago
We stayed a week at the cottage and had a wonderful time. The surroundings were so beautiful. There are quite a few beautiful towns nearby, perfect for day trips, but you’ll need a car, even to go to Castiglion Fiorentino, the nearest village. Fausto and Flavia were very welcoming and checked in us several times. The cottage was very clean and had everything we needed during our stay.

Villa in Castiglion Fiorentino
4.83 out of 5 average rating, 18 reviewsSuite Apartment ~ B&B Palazzo Robicci
SusanRating, 5 stars6 days ago
I just can’t say enough about how much we enjoyed our stay at Francesca’s. The massive and ancient masonry walls and window openings make for a magical atmosphere - and consistent indoor temperature. The garden and views are absolutely wonderful. There’s a fabulous restaurant on the same square and many great coffee shops nearby. And Francesca is delightful and knowledgeable. I highly recommend visiting Castiglion Fiorentino, and staying in this marvelous AirBnB!!
Guest favourite

Holiday home in Vitignano
4.97 out of 5 average rating, 34 reviewsPodere Vittoria Apartment: Heart of Chianti
CraigRating, 5 stars2 weeks ago
We absolutely loved this apartment, it was spacious and spotless, with modern bathrooms and the most perfect “farmhouse” kitchen. The view from the apartment and infinity pool was breathtaking. It’s the best Airbnb we have stayed in!
Guest favourite

Flat in Castiglion Fiorentino
5 out of 5 average rating, 5 reviewscasa Sonia
SilviaRating, 5 stars1 month ago
Perfect house, clean, quiet, and equipped with everything you need

Flat in Castiglion Fiorentino
4.54 out of 5 average rating, 26 reviewsthree-room wallbox included
MassimilianoRating, 5 stars1 week ago
Great accommodation at a really affordable price. Spacious, clean rooms, well-equipped kitchen, clean, comfortable, new bathroom, well-cleaned sanitary facilities. It was a pleasant experience at Daniel's, and when I return to Castiglion Fiorentino, I will definitely return.
Guest favourite

Apartment in Figline Valdarno
4.87 out of 5 average rating, 54 reviewsAgriturismo Casavecchia, l'Olivo
AnthonyRating, 5 stars3 weeks ago
We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.
Top guest favourite

Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 44 reviewsWine Loft in the vineyards
HilaryRating, 5 stars2 weeks ago
The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.

Home in Castiglion Fiorentino
5 out of 5 average rating, 3 reviewsBeautiful and cozy country-house, sleeps 11
AshleyRating, 5 stars9 months ago
Paolo's villa was beautiful! He and Marta were incredibly responsive and ensured we had everything we needed for a relaxing vacation. The villa feels luxurious and welcoming. It's a really beautiful location in Tuscany. I'd recommend going into Arezzo or Cortona for dinner or site seeing. The villa also has a host of amenities and recommendations. We hope to return!
Quick stats about holiday rentals in Castiglion Fiorentino
Total rentals
90 properties
Nightly prices starting at
₹2,596 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
40 properties have a pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Teatro Verdi
- Palazzo Vecchio
- The Boboli Gardens
- Santa Maria della Scala
- Nelson Mandela Forum
- Teatro Tuscanyhall
- Casa Barthel