
Vacation rentals in San Regolo
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Top-rated vacation rentals in San Regolo
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Other great vacation rentals in San Regolo
Guest favorite

Apartment in Pogi
4.94 out of 5 average rating, 89 reviewsBorgo Iesolana Suite Superior
RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Top guest favorite

Home in Castelnuovo Berardenga
4.97 out of 5 average rating, 35 reviewsCasa il Cipresso
DebbieRating, 5 stars3 weeks ago
Guilia, Donatella & Antonio were excellent to deal with responding very quickly to any questions. This is the cleanest air b & b I have ever stayed in and very well equipped (lots of coat hangers!!) The view from the patio at the rear of the property is so beautiful and peaceful. All we wanted to do was sit and enjoy the nature. Village centre only 5 minutes by car where there is several restaurants (best to make reservation) of varying price ranges. You can also walk into village. If you cross the main road at the bottom of the track to the air b & b you can walk on a track through the olive trees and come out in the village centre save walking on road). Small but excellent supermarket (closed on Sunday) 10 minute by car. Lots of interesting places to visit nearby. Enjoy your stay.
Top guest favorite

Home in Bucine
4.96 out of 5 average rating, 80 reviewsThe Biricocolo Cottage
PaulRating, 5 stars1 month ago
Serene, tranquil, verdant: a profoundly beautiful place. We just loved it. Chiara and her mother could not have been more friendly and helpful. We were there a few days for a wedding nearby. We can't wait to return for a full holiday. Well done super hosts! Thank you. Paul and Bridget
Guest favorite

Apartment in Castelnuovo Berardenga
4.88 out of 5 average rating, 26 reviewsColle ai Lecci: Design Apartment in Tuscany
JamesRating, 5 stars2 weeks ago
Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!
Top guest favorite

Home in Radda in Chianti
5 out of 5 average rating, 20 reviewsVilla le Scope 5*
ColeRating, 5 stars3 weeks ago
Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!
Top guest favorite

Farm stay in Greve in Chianti
4.98 out of 5 average rating, 59 reviewsCasa Giulia di Sopra Farmhouse
DarioRating, 5 stars3 weeks ago
What a great winery! The location is really unique, the accommodation is in the middle of the vineyard and very quiet. Alessandro our host was very nice, gave us a warm welcome and took a lot of time to show us everything (including the wines). We were also very happy with the accommodation, which was beautifully furnished and had everything we needed.
Top guest favorite

Cottage in Geggiano
4.99 out of 5 average rating, 133 reviewsVilla di Geggiano – Guesthouse
CharlesRating, 5 stars3 weeks ago
Everything about this place was magical and refined and peaceful. It was like stepping out of time and into a space of beauty and peace. Birds singing, frogs chirping, fire flies lighting up the night. Andrea was so friendly and so helpful and so generous. I definitely want to come back and stay longer. I can even imagine my daughter’s wedding there. We look forward to our next opportunity to stay!
Top guest favorite

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.
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- 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
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Teatro Verdi
- Nelson Mandela Forum
- Palazzo Vecchio