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Holiday rentals in Sestano

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Popular amenities for Sestano holiday rentals

Other great holiday rentals in Sestano

Guest favourite
Flat in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo 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 reviews

Tuscan 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 reviews

Crete 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 reviews

Casa 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 reviews

Two-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 reviews

Wine 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 reviews

Bed 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 reviews

XIII 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.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Sestano