
Holiday houses in Montisi
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Top-rated holiday rentals in Montisi
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Other great holiday rentals in Montisi
Guest favourite

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!
Guest favourite

Home in Asciano
4.94 out of 5 average rating, 36 reviewsFamily Forest - Pool in the Crete Senesi
JánRating, 5 stars1 week ago
The apartment really enchanted us, the rooms are nice, clean with air conditioning, stylish, in the living room a large TV, kitchen with everything that should be here. The "resort" itself was on a hill with beautiful views, a huge garden, a swimming pool, all stylish Tuscan, the surroundings beautiful, peace, quiet, peace, everything you need here you will find. As the Italians say, it's "Tutto bene" here
Guest favourite

Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 64 reviewsLuxury Tuscan countryside villa with pool/WiFi/AC
Devon And DavisRating, 5 stars1 week ago
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!
Guest favourite

Place to stay in San Giovanni d'Asso
4.93 out of 5 average rating, 70 reviewsVilla "The memory of time"
JoshRating, 5 stars1 week ago
Jaw-dropping beautiful location in a small valley, surrounded by scenery right out of a painting! The villa was perfect for our group of 7. We had plenty of parking for our 3 rental cars, and there was a convenient grocery store in nearby San Giovanni D’Asso. We ate twice at the nearby Trattoria Del Umbilical de Mundi, which was an amazing local experience! The kitchen is full service and we cooked several times, the above ground pool was very refreshing. And the amazing dining area inside is so large and grand we called it “The Situation Room”. Can’t recommend this place any higher it was a truly special experience. FYI at night it’s nice to take a walk up the driveway and see the stars and fireflies!
Guest favourite

Condo in Montepulciano
4.92 out of 5 average rating, 127 reviews"Dimora Valinda" Montepulciano Piazza Grande +A/C
CassiRating, 5 stars6 days ago
Maria’s place was beautiful and exactly as described! It was bigger than expected and had a cute balcony we really enjoyed spending late afternoons relaxing! We had a great time in Montepulciano, it was relaxing and slow paced after a busy few weeks before ☺️ Maria provided local recommendations and was always responsive. If you’re thinking of booking here I highly recommend!
Guest favourite

Farm stay in Campiglia D'orcia
4.91 out of 5 average rating, 470 reviewsPoggio Bicchieri Holiday Farm - Memoria apartment
RamonaRating, 5 starstoday
Super recommended! Flavia welcomed us in a very friendly and kind way, she gave us tips for great restaurants. The house is cozy, clean and is in a spectacular and very quiet location. We'll be back!
Top Guest favourite
Loft in Montepulciano
5 out of 5 average rating, 458 reviewsLa Piazzetta - Cozy open space in the historic center of Montepulciano
KatieRating, 5 starstoday
I wish I could give this place 10 stars! After a long day of travel, Guiliano welcomed us into the charming loft with cheese, crackers, Prosecco, cookies, and a bowl filled with ripe fruit. He also stoked the fridge with yogurt, cheese, eggs and a few other items. We made a delicious breakfast the next morning. The loft has the most picturesque postcard view. We just sat and stared often. The bed was extremely comfortable. There were also fresh flowers in small vases throughout the loft. It had so much character. 50 steps away from the front door is the main historic town with all the restaurant and shops. The town is extremely beautiful. This was better than any 5 star hotel. If it is available, Book it now!
Guest favourite

Farm stay in Montepulciano
4.97 out of 5 average rating, 89 reviewsUnique view 3 bdr villa with pool & A/C in Pienza
MarciaRating, 5 stars2 weeks ago
Andrea’s house is one of my favorite Airbnb’s ever. The setting is gorgeous - sitting outside with coffee in the morning was a highlight for me. The house is even better than the pictures, the pool lovely, and both Andrea and Ramona were extremely helpful with recommendations and responsive to questions. It truly felt like being a welcome guest in someone’s home.
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Lake Bolsena
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Kite Beach Fiumara
- Marina di Grosseto beach
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cala Di Forno
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Tenuta Le Velette