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

Flat 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 favourite

Guest house in Macciano
4.96 out of 5 average rating, 165 reviewsTuscan cottage with an heavenly view
BridgetRating, 5 stars6 days ago
I can say enough about his beautiful Airbnb. My husband and I stayed for four nights, and Alistair and Maria were the most gracious hosts. From start to finish we felt welcomed and cared for, and the cottage itself - not to mention the grounds - was simply gorgeous. Nestled in the little town of Macciano, the cottage has great proximity to so many beautiful towns, attractions, and restaurants. We took multiple little day trips and were able to cover a lot of ground, and still be home in time for a dip in the pool and a glass of Prosecco with our charming hosts. Maria even offered to cook with me one night, and I had the opportunity to learn about the local fare, all lovingly made from scratch by Maria. This is a very, very special place filled with beauty and tranquility. We can't wait to go back!!
Top guest favourite

Cottage in San Martino in Grania
5 out of 5 average rating, 42 reviewsCrete Senesi - Asciano Cavoni Hut
InezRating, 5 stars2 weeks ago
Laura is the perfect host and the house is really amazing: very large and stylish, with a nice private garden and pool area. The best rental place ever!
Guest favourite

Villa in Asciano
4.93 out of 5 average rating, 88 reviewsCasa Bianca, a gorgeous Tuscan home in Crete Senesi
JulieRating, 5 stars2 weeks ago
Photos do not do justice to the amazing views. Very special place.
Guest favourite

Barn in Le Mura
4.89 out of 5 average rating, 47 reviewsTwo-room apartment in a Tuscan barn
JaapRating, 5 stars4 days ago
Had a great stay in this place! Very friendly people, and a really clean facility! More than 5 stars!! Would stay there again for sure!
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.
Top guest favourite

Home in Castelnuovo Berardenga
4.91 out of 5 average rating, 200 reviewsBed and Breakfast CASA CERNANO
KarlaRating, 5 stars4 days ago
We truly enjoyed staying in Catherine’s place. It was the perfect spot after being in Rome for a week. Her hospitality, peaceful days and the Tuscan landscape were just what we needed! Catherine was also so helpful at recommending things to do in the area, and we enjoyed them all! We hope to be back to her place one day!
Superhost

Villa in Siena
4.8 out of 5 average rating, 272 reviewsXIII Century Tower with Private Panoramic Pool
PaulaRating, 5 stars1 week ago
Our family had the dreamiest stay at Alessandro’s. We had a large family of 12 and had plenty of place to sleep with plenty of bathrooms. About a 20 minute taxi ride from the main siena center. We also had our own private pool which was a short walk through the olive trees. We enjoyed the wine from the property, cooking class with Stacey, and enjoyed a wonderful private dinner in the outdoor courtyard. Laura was also very responsive to anything we needed during our stay. Our family had the most memorable stay! Would 10/10 recommend staying here.
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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
- Mugello Circuit
- 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