
Holiday houses in San Polo in Chianti
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Top-rated holiday rentals in San Polo in Chianti
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Guest favourite

Condo in Centro Storico
4.97 out of 5 average rating, 119 reviewsLuxury Suite Pinti (frescoed suite in the centre)
DavidRating, 5 stars1 week ago
Yes, it is spectacular for all the reasons mentioned by others. The frescoes in the rooms and loggia are most remarkable, and of great historical significance. There’s a manual on site that details all the history, and additional information can be found online on Wikipedia and elsewhere about the frescoes and the garden. Gian is a most excellent host. Thank you thank you thank you.
Guest favourite

Apartment in Centro Storico
4.96 out of 5 average rating, 91 reviewsPanoramic loft with terrace near Ponte Vecchio
SethRating, 5 stars2 weeks ago
This was the perfect place to stay! Just minutes to the bridge leading to city center along with some fun spots right outside the door. Lots of steps but WORTH IT! The view from the terrace was great and the apartment itself was better than we could’ve asked for! Would definitely recommend this spot to anyone else planning a trip to Florence!
Top Guest favourite

Apartment in Centro Storico
5 out of 5 average rating, 114 reviewsSuite vista parco - Bracco Florence G.V.
ShawnaRating, 5 stars5 days ago
Giovanni and llenia were the best hosts I've come across. From their immaculate apartment to cleanliness and stocked fridge was unmatched. Thank you for providing a home away from our home! We HIGHLY recommend booking with this couple. Walkable restaurants, close to a sweet park and boutiques. Thank you, thank you, thank you!
Top Guest favourite

Villa in San Casciano
4.97 out of 5 average rating, 110 reviewsLuxury Villa in the very heart of Chianti
MelissaRating, 5 stars1 month ago
Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!
Top Guest favourite

Villa in Rignano sull'Arno
5 out of 5 average rating, 16 reviewsvilla "La Fonticina"
ClaraRating, 5 stars1 day ago
The villa is beautiful and the host Cesare is incredible. And I mean incredible. We have had excellent hosts before but he is beyond belief. He even helped us when there was a train strike by picking us up in Florence. He is warm, responsive, friendly, funny. He answered every text in a minute. Family with kids went and the place is beautiful, spacious and the pool is large and fabulous. It was the best week of our vacation. We also had a wonderful cooking class at the villa that Cesare recommended. Gabriella was so much fun. Florence is 30 minute car or a train ride but we always took train. We hope we can return.
Top Guest favourite

Home in Vaiano
5 out of 5 average rating, 243 reviewsThe MOONLIT & SUNNY COTTAGE near Florence
MeganRating, 5 stars4 days ago
This place is absolutely stunning! Alessandro is the most amazing host- very flexible with our late check in and early leaving time- even brought us a cappuccino at 3:30am before we left! Couldn’t recommend more- we will definitely be back- thank you for the most amazing stay!
Guest favourite

Loft in Centro Storico
4.96 out of 5 average rating, 422 reviewsCharming and quiet loft with garden
RaeganRating, 5 stars1 week ago
Guillaume & Giulia’s place was absolutely beautiful. Both they and their property manager Duccio, were so responsive, helpful, and wonderful to us. They had a great book of very good recommendations (for all budgets and tastes!) in the Kitchen with very detailed instructions/tips and tricks. You could really tell they put a LOT of effort into creating this for people to benefit from, and the whole space felt like this as well. It was so homey and lovely. Honestly the best stay we’ve had in all of our travels within Europe! Thank you so much for having us, if we ever find ourselves in Florence again, we will be sure to book with you and would recommend you to anyone we know!
Guest favourite

Apartment in Castelnuovo Berardenga
4.93 out of 5 average rating, 161 reviewsVilla di Geggiano - Perellino Suite
RachelRating, 5 stars2 weeks ago
This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.
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- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Ponte Vecchio
- 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
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Pinocchio Park
- Teatro Verdi
- Nelson Mandela Forum
- Palazzo Vecchio